Why Are Gay Friendships So Hard?

[00:00:00] Michael DiIorio: Welcome to Gay Men Going Deeper, a podcast by the Gay Men’s Brotherhood that showcases raw and real conversations about personal development, mental health, and sexuality from an unapologetically gay perspective. Today, I’m your host. My name is Michael DiIorio. And joining me is Pepper from the Gay Good.

Today we are doing an expose on gay friendships. We’re lifting the hood on that polished exterior and revealing what’s really going on beneath the surfaces in our friendships. The competitiveness, the cliques, the fakery, and that quiet loneliness that so many of us feel but don’t talk about.

But this episode is not just about throwing shade on gay friendships. We’re really actually going to unpack what’s going on beneath the surface. And because ultimately, what Pepper and I want you to get from this episode is understanding, first of all, that you’re not alone in feeling alone in your friendships and offering a pathway to friendship that actually feels good, nurturing and fulfilling to you. So returning to the show today to help me with this is Pepper from the Gay Good. Pepper, say hi.

[00:01:12] Pepper: Hi. Thanks so much for having me.

[00:01:15] Michael DiIorio: And guys, just so that you know, this topic was actually inspired by a few things, but Pepper did a couple posts. Maybe you can share them later in the links about some issues with gay friendships and green flags. So we’re going to be using that as our basis today. Now, if you’re new here, please subscribe to the channel on YouTube. And if you’re listening on your favorite podcast platform, please subscribe and leave us a review which helps us get into the ears of the people who need us. And remember, guys, this podcast and YouTube channel are listener and viewer supported. So if you enjoy what we’re creating here, you can support us by making a donation to the show and using the link in the show notes. You can also tap on that thanks button on YouTube to show us some love.

All right, let’s get into it. Let me talk about why I wanted to do this episode. I’ll do a little intro here. I’m going to put my coach hat on for this bit here. So I coach in one week, anywhere from 15 to 20 guys, most of whom are gay, bi, or queer. So I say this with authority. Our community is struggling with friendship. And what’s worse is we are afraid to admit it because no one’s actually talking about it. So what’s worse is we’re not talking about it. And then you look on social media and it looks like everyone else has a crew, has this chosen family, has a clique, and they’re having fun and they’re kikiing with all their gay buddies. And so it’s really easy to fall into that compare and despair trap of, oh, they have it and I don’t. But my friends, let me tell you, when we take a deeper look into those gay friendships, not all of those are what they seem on the outside.

Some are very performative. A lot of them are overly shady. Some are outright toxic. And again, I say this with authority. Some of the loneliest men I’ve met are the ones who on social media look like they have lots of friends.

An astounding number of gay, bi, and queer men are actually craving real friendship, genuine friendship, not just that performative, what it looks like on Instagram kind of friendship. Friends that are fun. Yes. Friends that you can kiki with. Absolutely. But also friends that you can feel safe with and that have that nurturing, nourishing sense of connection. I call it friendship that soothes the soul. When I think of my closest friends, sure, we can be kicking, having fun, and even throwing shade with each other, but ultimately, when I’m done, like, hanging out with them, it just soothes my soul. It fills my cup, not drains me. So instead, what I see a lot of guys are doing out there are settling for that ultra shadiness, competitiveness, and fakery and then calling it friendship on the outside.

So in today’s episode, we’re unpacking that. We’re unpacking the pretty lies we tell about gay friendship and the ugly truths that keep us from the friendship that we deserve. And we’re going to be doing this episode in three segments. So one, we’re going to be looking at the shady side of gay friendships, and then we’re going to talk about what’s going on beneath the surface. And finally, we’re going to pivot towards what we actually want from our friendships and how to get it. All right, so let’s start off. Pepper with the pain points here. What do you think gets in the way of fostering true gay friendship?

[00:04:14] Pepper: Yeah, I think something you said in your intro, which, by the way, hats off to you. That was a great intro. You ate that. Michael, something you mentioned was the word settling. And I think scarcity has a lot to do with it. We are a mighty community, but at times it feels like we’re a huge community, but we’re not that big of a community. You know, when you’re in college or boarding school and when you first get there, it’s kind of like a mad rush to make friends and everyone’s best friends within a week. And then you start seeing the cracks in those formations a few weeks later. I felt just like that when I first moved to Los Angeles and I didn’t know anyone and I started making queer friends here and there and those relationships developed a little bit quickly. And now looking back, it really was a lot like settling. Those friendships were based on superficiality. They were based on when are we going out? Who are you dating? Is that guy cute? I feel like many gay, queer, bi men don’t have necessarily the tools, especially when first coming out, to get deeper in their relationships to talk about what’s really on their mind. What are your insecurities? What are you comfortable? What are you not comfortable with? Do you even want to be going out tonight or are you just doing so so you’re not feeling alone, you’re not looking alone, you have something to post on social media. So I feel like we don’t always have the tools, especially when coming out, to advocate for ourselves or to look in the mirror and ask yourself, is this person, like you said, soothing my soul? How do I feel when I leave them? When I think of my friendships taking a step back, A big reason I’ve made a number of posts about queer friendship over the past year and a half is because I’ve really started being very intentional about who I give my space and time to think. Over the past year and a half, I’ve noticed what friendships weren’t necessarily serving me, what friendships sort of looked good on social media and I’ve sort of reprioritized, I guess, people in my life. Not in a shady way, just in a sort of looking for that connection and that soothing. But it took a lot of time for me to get to a place in my own discovery and growth in my coming out journey to to ask myself those questions of how am I feeling? What do I want in my friendships? What’s being reciprocated? Was that shade that went too far, Was that fun, playful shade because I can take a read and I love that. I’m actually thinking about having a roast for my birthday. But then there’s a difference between the shade that seems like it’s coming from an honest place and seems like it’s coming from a place that was meant to hurt you.

I think sometimes we just don’t have the tools to ask ourselves those tough questions. Perhaps it comes from a place of being closeted for so long and just wanting to get by, maybe being out of the closet and wanting to find that group, desperately wanting to find that connection. So you settle for these friendships that aren’t necessarily serving you and you settle for friendships with these guys that perhaps don’t have your best interests at heart. And I think that comes from a lot of pain, perhaps shame as well.

And yeah, I’ll start with that. It definitely comes from a lack of tools and social awareness for how you are feeling and what it feels like in this friend group. Because we didn’t really, I’ll speak for myself, I didn’t have that growing up. I didn’t have a group of friends.

And it took me a while once coming out to really sit in those feelings and think about how is this actually landing on me? How do I feel when I’m texting these people and making plans, you know?

[00:07:54] Michael DiIorio: Yeah. And I think it’s important that, I mean, at least the way that I’ve had my closest friends show up and a lot of my friends is, it can start in that fun. Are we going out tonight? What are we doing? Is like, I like all that stuff that you said.

[00:08:06] Pepper: That’s great.

[00:08:07] Michael DiIorio: I still do that with my closest friends. Right. But the difference is like there is the option to go deeper if and when I need to. So if I’m having a bad day or I want to talk to someone and I’m having a hard time with something, I can easily call up those same friends who we can have, yes, surface level conversations and say, hey, listen, like let’s talk about this thing that I’m going through and I know for sure that they’ll be able to hold me through that and we’ll be able to have that in depth conversation where I can let down my guard and be vulnerable. I think that’s the difference. So we’re in. And we’re not saying that that has to be the only way to have it, but I think what we’re advocating for here is let’s play in both ends of the pool.

[00:08:44] Pepper: Speaking of the pool, I remember first moving to Los Angeles and meeting one gay guy, then another gay guy. And then I think social media as you touched on plays a huge role in this. I can vividly remember like being alone in my bed, like clicking on this guy’s profile and saying, oh, he’s at this pool party. All these good looking guys and their speedos. I want to be a part of that. I want to meet them. Just got to this city. This looks amazing.

And I kind of got lost in that vision and in what I felt like that life must have been like, you know, I live In Los Angeles, but it’s different in every city. But there are certain, I guess, aspirational places and posts and where you feel like, why am I not a part of that? If that’s what you’re looking for and we can talk about it. There’s plenty of other venues and spaces to foster queer friendships. But those posts that blow up and get the likes and looks like everyone has abs and they have their high noons and their trulies and they’re having a good time. I kind of got lost in the performance art of that and really wanted to be a part of that, that scene in my early 20s when I first moved here. And when I look back, even before I was invited to those parties and got to know the peoples in the photos, I definitely developed a bit of a negative self critique on myself. I’m like, well, my body doesn’t look exactly like that and oh, I don’t think I can afford that Speedo Lion. And it sounds really shallow looking back, but that’s where my mind went, you know, as a young gay boy looking at these guys and thinking, oh, so I guess that’s what I have to look like and that’s what I have to buy in order to fit this scene. And in my years of like 23, 24, 25, it was a lot of wanting that and pushing my body to a limit that wasn’t necessarily healthy to one just not be alone. I feel like that’s the greatest thing we struggle with is that feeling of connecting. Especially when first coming out, that rush of freshman year of college and there’s so much happening, it’s so overwhelming.

And I would sit there just thinking, well, if that’s what I have to do and if that’s what I have to look like, then I guess that’s the path I have to take. And I didn’t have the tools or the foresight yet to consider other options. Or again to ask myself, what am I actually looking for in friendships? I think social media definitely clouded that for me and that’s one of the reasons I started the gay Good. One of my very first posts, which started it five years ago now, just a little insane, was five years ago last week. So I was looking through my first post to be like, what was I posting about originally? Like, where did this come from? One of my first posts was all about these images, these bodies, they could have been edited. Like you don’t understand what goes through the lens and the editing process while you’re looking at these photos of these fabulous Friend groups, and I’m sure we’re about to get into it, but you don’t actually know what goes on at these parties and how people are feeling once that photo is taken and uploaded.

[00:11:47] Michael DiIorio: Oh, my gosh, I love that you said all that. And I think for you, your experience was your early 20s. But I want everyone out there to know that this is still what Pepper just described. There is very real. For people that are in their 30s, 40s, 50s, this is still very much the case. And that would be my answer to what gets in the way of fostering true gay friendships. If I had to pick one, and I could pick more than one, but I don’t want this just to be a shit talk. But I would say that tendency, if you will, to use friendship more as a social currency than as actual genuine friendship. And this is exacerbated for sure by social media and Instagram.

[00:12:29] Pepper: And.

[00:12:29] Michael DiIorio: And one of the things I’ll ask people is like, are you looking for friendship or followers? Because it’s so clear to me when I’m out and about with the gays or wherever, whatever event, it’s like, oh, yeah, add me on Instagram. Add me on Instagram, add me Instagram. And I’m like. And then like, do you even talk? Like you just want that follower and then you want to take the picture with that follower, Especially if you know he’s got a lot of other followers that you might want to be like, it’s just this constant game almost of like, we’re just exploiting each other for follows. And it’s a dynamic that we need to stop and that also exists. Azerbaiz. A whole bunch of other things here. I’m gonna go into a rabbit hole and I get a little bit fiery on this topic, so I apologize, but fiery.

This whole notion of like the a gays, I hate that when I hear that word, I’m like, oh, it grates me. And not much grates me. But that is a dynamic we need to completely stop.

There’s no such thing as that. And let me tell you, those a gays quote unquote, that you’re talking about are probably, again, they probably have some of the most toxic friendships or connections. Again, if you look beneath the surface, I’m not saying everybody, I’m just saying that that tends to be the case. But be careful of that story you tell about these people.

Now, here’s the thing we can try, as you had said, Pepper so much, and I’m guilty of this too. When I had first moved to the city. Okay, this is how I need to look, and this is the clothes I need to wear and have to get these kinds of shoes, and I have to get that kind of body and have that kind of hair. These are, like the unspoken rules of, you know, gay culture and gay friendships. And, you know, just go to any beach or circuit party or any gay event and you will see very quickly that, sure, you can fit in and you can be part of our group if you are within this age range, if you look this way, if you wear these clothes, and I’m going to even say it, if you are a certain skin color, God forbid, my friends, if you are older, if you’re the older one in the group, or if you are not fit as the others, or if you are not as masculine presenting or you’re not wearing the right Speedo or you’re not wearing the right accessories, and even if you are black or brown or the Asian one in your group, right? And yes, I’m calling all y’ all out. As a white guy, I can safely say that we are excluding other people, whether we know it or not, because they do not fit.

So I think that has been what I see as an observer, as a casual observer now, but even when I was younger. But I know this is happening now, and we, you know, it’s easy to say, oh, yeah, that’s just for people in their 20s and 30s. But no, my friends, I’m 42. It’s still happening. I still see it. So it is very exclusionary and it’s very annoying because we create this echo chamber of people that we think we need to look like. But that said, it’s just about the look and not about the true connection.

[00:15:15] Pepper: Yeah, I think a lot of that goes back to I mentioned, like, the tools we might not be equipped with when entering the gay scene. And, like, beautifully said, that can be at any age. For me, it was my early 20s. For others, it’s 30s, 40s, 50s, or even earlier. Younger than your earlier 20s. You know, for me, the way my. My closeted life was, and I always am weird about admitting this, I was a fuckboy. I’m a fuck boy in high school, dated a lot of girls, a player, very masculine, Miami. So weird to admit 10 years later, not because I’m ashamed of it, but just it feels so like, that’s not me.

But because of that, I was so equipped with the skills of deception and lying and passing as something I wasn’t. And I feel like other queer men might relate to that. So when you do come out, you still have those skills and you still play to those potential strengths, those, like, dark strengths of lying and putting a smile on your face when you’re not actually smiling and just getting through the day or the party to fit in and to look the part and to not look alone. So there’s a lot of sacrifice, self sacrifice, self joy, self fulfillment. I feel like queer men do in practice in order to fit the scene or to make it look like they have all these friends around them. I remember being invited to a party about a year and a half ago by this guy I met maybe once or twice. Really fun guy. Big, big following on Instagram, even more so on Twitter X. And I was like, why was I invited to this? My roommate was invited too. And we kind of clicked to us both at the same time. Oh, he just wants to fill the room. He just wants it to look like there are 40, 50 plus guys there celebrating him. And made us kind of sad because, yeah, this is a party. Great. Let’s go have fun. But then I wondered, like, how many people there are close friends of his. Like, do you exhibit the green flags and the beauties of queer friendship? We’ll talk about later in this discussion. And who are you inviting? Just to have that look of a big, fabulous gay lifestyle. And I see that room filling and those, like, patterns of deception or performance art, if you want to call it that, that a lot of queer men practice in order to, again, fit that bill and have that photo and that illusion that everything’s right and that they found their way and their tribe and they’re thriving, they’re successful. You know, all those buzzwords you want to throw in there.

[00:17:55] Michael DiIorio: Yeah, exactly. And I’ve seen that play out myself. Like, I’ve actually witnessed that happen.

Uh, Pepper, did you ever watch White Lotus season three?

[00:18:02] Pepper: No.

[00:18:03] Michael DiIorio: Okay.

[00:18:03] Pepper: Don’t watch a lot of things.

[00:18:05] Michael DiIorio: Anyone out there who watched White Lotus Season 3, and I know a lot of y’ all did, there are in the last season, three girls, three friends. Jacqueline, Kate, and Laurie, and the arc there.

I think a lot of gay guys can relate. It’s these three girlfriends who go on a trip to Thailand, and they’re like, they’re kind of kicking and having a time, but beneath the surface, there are these very complex, even toxic dynamics between these three women. And it kind of reminds me of what you were just saying. Like, we’ll make this post on Instagram and I’ll tag you. And it looks like we’re like, best friends. And then like, as soon as you turn around, I’m going to be talking shit about you and like dragging your name through the mud. And I see that happen so, so much. And if you watch White Lotus, this is kind of what happens in the, in that storyline, but I won’t give it away.

[00:18:51] Pepper: Yeah, and that happens a lot too with the shit talking.

[00:18:54] Michael DiIorio: Yes.

[00:18:54] Pepper: As I, as I spoke about, like, kind of reprioritizing my friendships and like, who I’m spending my time with there. I can think of one friendship where I didn’t really like him, but we were, we were really close friends, which is still kind of a mind fuck to speak about now. And that was one of the friendships that like, made me start thinking, like, what am I actually looking for? Who am I going to spend my time with? But it was a lot of like, venting and trauma dumping and then turning around and perhaps not saying the most flattering thing about him, which I can own up to. I know it happened the other way and things were said about me and it gets me thinking, like, why are, why are we stating we’re such close friends when there’s so many things we don’t actually enjoy about each other? There are a lot of things we had in common and sure we looked good together in photos and had a lot of the same interests and like to go to the same parts of towns and same parties, but looking back at that friendship, while I wish them the absolute best now, it’s, it wasn’t a true friendship. There was a lot of mistrust there that at the time I was willing to, I guess, deal with or give a pass to. And I think that goes back to the scarcity of it is a lot of gay queer men don’t have the capacity or don’t feel ready to open up. So when you do open up to someone, you kind of like latch on for better or for worse.

And it takes some time to, to think and to process, like, am I latching on to the right person? What else is serving me here other than the fact that I just dumped all this shit on them and they seem to dump some back and we’re, we’re trauma bonding.

[00:20:30] Michael DiIorio: Yeah, I think a lot of friendships are, are in that category as well. Well said.

Let’s take a moment now to check in with our audience. So Pepper and I have been sharing a lot of our own dumping on what we think are the barriers in, in developing true gay friendships. So let us know in the comments if you’re watching us on YouTube. What’s been your biggest barrier in developing genuine gay friendships and viewer, listener. If you are enjoying the conversation that we’re having here, I want to invite you to our weekly events within the Gay Men’s Brotherhood. Okay, this is the antithesis of what we were just talking about. In the Gay Men’s Brotherhood, we have sharing circles and Connection Circles. We have one each week. Sharing Circles are where you have a chance to share in a bigger group setting the topics that we discuss here in the podcast. You can come and join us. You can share if you want to. If you want to just be a passive listener, you can do that too. We also have our Connection Circles, which are a little bit different. In our Connection Circles, we take everyone in the room and we put you into breakout rooms of three, and you guys go in those rooms and discuss certain topic conversations that we have similar to what we do here on the podcast with Matt and Reno and I. So if you’re interested in any of these events, please go to www.gaymensbrotherhood.com and check out the events section to RSVP. Now, don’t worry if you don’t have Facebook. Not a problem. Just make sure you get on our email list and we will email you the Zoom link. All right, let’s pivot now, Pepper, and talk a little bit about what’s really going on beneath the surface. We touched on it a little bit with the fact that we weren’t taught this and we might have some wounding and trauma from our childhoods and coming out. So why do you think so many gay friendships stay surface level or. Or performative? What’s really getting in the way of that deeper connection?

[00:22:11] Pepper: I think unfortunately, a lot of us carry a great deal of shame, a great deal of embarrassment, a great deal of narratives and trauma that has been under addressed. A lot of, and I’m sure you’ve seen this, there’s a hesitancy perhaps in your clients, the men you work with at first to. To open up, to let loose a little and show the good, the bad and the ugly.

And because of that, we’re not really sharing what’s on our minds. We’re not sharing. Oh, I’m actually not too comfortable with this plan. I’m not sharing. I’m having a bad day. I’d rather not go out. You want to just come over and chat?

We’re not sharing the fact we might be going through a moment, whether it’s a sexual health moment that we might be scared of and not comfortable talking about, whether it’s a relationship that is a romantic relationship that you’re having troubles with. Perhaps there’s some infidelity going on. Just an example. Going back to not having the tools. Sometimes we’re afraid to show the less pretty parts of what’s going on. So we tend to stick to the script of, well, let’s talk about Drag Race, and let’s talk about the new Charli XCX album. And let’s talk about, oh, that cute boy over there, which is all good and fine. And, you know, I’ll do that every day of my life. That’s fun. But every day of my life, too, I want to talk about what’s really going on and what I’m struggling with and parts of myself I’m working on.

And there’s a vulnerability that’s missing sometimes in these friendships that’s preventing people to go deeper and to, you know, grasp onto the green flags. We’ll talk about that. Really do make those relationships that, as you mentioned, feel like are soothing your soul. It’s that lack of vulnerability to really. To really go there with someone and to go there in a intentional, loving way that’s filled with, you know, compassion and understanding and a little bit of liberation, if you will.

[00:24:07] Michael DiIorio: Yeah, I think that, you know, I’ve had the benefit of coaching a lot of guys on this very topic about authenticity vulnerability, not just platonically, but even romantically. So this applies to that as well. But we’re going to focus on Teutonic friendships today. You know, it’s important to realize that for a lot of us, depending on your coming out story, when you came out and how you came out, a lot of us learned that being ourselves, being authentic, was not safe. And we learned that at an early age. Right. I’m speaking for myself here as well. I learned to default to inauthenticity and performing and faking it, really, because to be myself was to come out. And that put me in danger.

Sometimes physical danger, but mostly emotional danger. I mean, I was a teenager when I. When I knew that I was gay. And so I became really good at playing the part. Similar to what you were saying about being that fuck boy in high school. But for me, that lasted kind of well into my 20s, and for some people, it’s lasting into their 40s and 50s and beyond. So, you know, we have to remember that when we default to that our brains are. Our wiring is really good at saying, hey, let’s play the part. And that authenticity, in fact and vulnerability, in fact, is scary. And it’s something that we don’t want to do. And actually revealing our true selves and our vulnerability is a dangerous thing because in those days it led to, or could lead to rejection, abandonment and disconnection. Like exact opposite of what it is that we want. So that survival strategy that may have kept me safe in high school has now become a barrier to the true friendship that I actually want in my 42 year old brain. And that’s the vulnerability we need to like say, oh, this is something that I don’t know how and have learned is scary, is actually the very thing I need to move towards to have connection.

[00:25:54] Pepper: Yeah, that’s tough. And on the flip side of that, I’ve noticed that the more vulnerable you are, the more selfless you are with, with your inner demons. Not only the closer do I get to my friends, but I feel like it gives them a bigger snapshot into what’s going on in my mind. Earlier this year, I’ve come to realize that I still struggle a bit with the concept of friendship abandonment. I had a few friendships in college that I thought would span my entire lifetime and they seemed to have dissipated within a year of me moving to la. And then Covid hit, so I had thought I worked on them. And then watching episodes of the Real Housewives of Salt Lake City, Mary Cosby talked about being in a dealt with abandonment issues. And it really struck me and I struggled with that for a week and then told some of my closer friends about that sort of rediscovery. That I do fear abandonment and friendship. And perhaps that’s why I was sensitive when this happened, or perhaps that’s why I took this event a little bit more to heart. And having those discussions were really, I’d say, triumphant in even furthering our friendship along. So they know what my particular sensitivities are. And that if I now know, if something ever does struck me in a way, or I’m feeling insecure or maybe even slighted due to the work I still need to do, I am more than comfortable to share that with my friends.

So when it comes to vulnerability, I feel like that’s something I never would have done three years ago, four years ago. It didn’t seem safe. It felt selfish in some fucked up way.

And now I share those moments a little bit more willingly. And it’s definitely come to a brighter place and a closer place with the friends I do consider near and dear now.

[00:27:48] Michael DiIorio: And yeah, those endings of gay friendships, when they happen, hit really hard because of everything that we’ve just been saying right from the beginning how, first of all, there’s so few of us. So when you do meet someone you get along with, it’s like this sacred, beautiful thing. And when it ends, it equally hurts just as bad. And actually something else you just. I just thought of as you were speaking was like, when you were talking about that, I imagine, like, collaboration, like two people coming together, moving close towards each other, like, connection. And yet what happens so often in the gay culture, it’s competitiveness. And it’s not always spoken, actually. In fact, it’s not spoken very much at all. But it’s there and you can see it. It’s just under the surface. It’s palpable. Again, if you go into groups of gay men, especially if we’re at a beach or at the pool and our bodies are out at the club, that competition of, you know, looks and bodies and success, that envy, that compare and despair, absolutely kills that collaborative connection energy, you know, oh, he has a better body. He has a nicer house. He has a. He gets more guys than I do. He’s having more fun than I do. He’s getting more attention. He’s got more followers. Whatever that is. It’s there. And I think for a lot of people, yeah. And this is unsaid, but I’m going to say it. I think it’s simmering beneath the surface and it prevents us from getting close to one another because there’s that envy. And part of me wants to, sure, maybe I want to connect with you, but also, like, I kind of want to take you down.

[00:29:11] Pepper: Yeah, that’s definitely there. And there’s a part of me that’s like, oh, I can’t believe we haven’t talked about that yet. But I feel like the reason is because we all know that. You know what I mean? Like, we sense that. One of my most recent posts on the Gay Good was about, you know, when you meet a gay guy and just something seems off and it kind of seems like you’re sizing each other up. And I got a lot of response to that just based off a quick interaction I had in Chicago last month. And I’m like, I can’t be the only one that’s going through this. And, like, this weird, like, are we friends? Are we kikiing? You just laughed at what I said. But, like, do you hate me?

Which sounds so weird to say out loud, but it happens all the time in our community. And it is this little competitive storyline that seems to be, as you mentioned, simmering beneath the surface almost constantly. And my way to circumvent that was just to start chatting and get out of your head and get into your the moment and be present and, you know, ask that guy that you might be having a weird first impression of more about him. And, hey, what are your hobbies? What makes you happy? What is something you’re looking forward to this weekend to just sort of break that mind fuck that we feel sometimes and get into more of an honest conversation at a regulated pace that can potentially, hopefully lead to, you know, a more compassionate discussion and more of a seeing each other instead of conflating all of the things running through our minds when interacting with a new queer man.

[00:30:41] Michael DiIorio: Yeah, let me give you a great example of this that happened with me.

Was it last year? But anyway, I was recently came out of a relationship. It was my first Christmas after my relationship, and all of my best friends, all my besties had partners. And so New Year’s Eve plans come around and it’s like, oh, fuck. Like that, that sinking, like, oh, my God, they’re all going to be doing something, and I have no one to do anything with. Am I going to be here all along?

So I could have just been said nothing about it and kind of quietly resented them for having all these lovely relationships to enjoy New Year’s with. But no, what I did is I said exactly that. I said, hey, guys, I just want to put this out there. Like, New Year’s Eve is coming, and I’m feeling a little bit on edge. I’m feeling a little bit, like, sad, because I know y’ all are going to be with your boyfriends, as you should. It’s New Year’s Eve, but I’m feeling like I’m going to be at home and it’s going to be a bit of a hard moment for me. And just naming it was good enough as it was. But fortunately, you know, one of my friends was like, hey, listen, why don’t we have a little house party? We can all be together. Yes. We’re still going to, you know, kiss our boyfriends at midnight. That’s all fine and dandy, but at least you’re not alone for years. And so that moment, first of all, we have nurtured that connection over years. These are the chosen family that I’ve had before on the podcast. We had a culture where we can, in our friendship dynamic, where we can say these things, right? It’s not out of the norm necessarily. And even if they didn’t, even if they weren’t able to offer that for me, it still would have felt good that I named it. And they still would have probably checked in on me and messaged me at 12:01 to say, Happy new year. We love you, Michael.

[00:32:15] Pepper: Yeah, that’s special. Thanks for sharing.

[00:32:18] Michael DiIorio: Yeah. And I think that’s kind of. And this is a great segue for our next section. That’s kind of the friendships that I would love gay, queer, bi men to have where you can open up like that and really reveal the truth of where you’re at emotionally.

Okay, let’s check in with our listeners and viewers again. So I want you to check in and reflect on your friendships. What gets in the way for you when it comes to having a deeper connection? And I want you not to think about in this particular question, not to think about other people and, like, what’s wrong with other people? But to ask yourself what within you is holding you back from maybe being more vulnerable and having those more intimate conversations? And if you want to take this topic to the next level, we do have several online courses and coaching videos within the gaming going deeper coaching collection. That is our collection of two courses and 45 coaching videos that you get lifetime access to. One of the courses is called healing your shame, and then the other one is called building better relationships, which is very much focused on the conversation we’re having here today. And you get lifetime access to all of this when you go to www.gaymangoingdeeper.com and you can check out an entire module on platonic friendships, community and vulnerability and authenticity. All right, Pepper, let’s talk about the friendships we actually crave. What does a truly nourishing gay friendship look like to you?

[00:33:40] Pepper: I feel so blessed and happy to have my tribe now. It’s like six of us. What I like the most about us is we don’t really look like each other. There’s a big age gap. I think our youngest just turned 23. Our oldest is turning 39. So it’s a bigger gap than you see in most groups. And I think in that and talking about vulnerability again, as we talk a lot about the struggle, just in the past year, our friend group has undergone losing jobs, losing housing, losing relationships, health woes, anxiety, mental health, et cetera, et cetera. And we go there with each other. We show up.

Yes, we’re still having fun. We’ll go to this party. We’ll go to this pool party. We’re at the beach all the time. And that’s. That’s amazing.

But I know 100% that if something is going on, if shit is hitting the fan that I I can call them and that they will help scrub the off the fan with me. And it’s happened and they’ve shown up for me and I’ve shown up for them. And it’s having the tools and the courage to reach out and say I need help.

And also the feeling of knowing that help will be received and I will be going there too. The showing up is really important. Whether that’s answering a phone call, whether that’s taking someone to dinner if they had a rough day, whether that’s helping someone move or move their boxes into storage. These are all real examples of what I’ve seen myself and my friends show up for each other in the last year.

And that is what I’ve been craving. It feels like a little village of men who are supporting each other in their careers, looking at our resumes, looking at job applications together. It feels very much like we’re all in this together. And when I think of community, that’s everything I ever wanted. Right now I’m not as concerned about how hot the photo looks. I’m just, I want to take as many photos as I can. Whether it’s a derpy face or not, I don’t care. And I don’t care enough to post it. I just want to have it. And sitting in that soul soothing feeling.

I think some certain other, I guess green flags I can talk about that I put in my post I was inspired by these Friends are one we can laugh at each other and ourselves and know the difference between loving shade and again, that biting shade I talked about earlier. Like I love to take a joke and queerness can be so silly. And our lives and sex lives and what we, everything we go through can be so ridiculous at times that like being able to laugh about it really does make a big difference. And also just a strong maturity is something I really look for. Friendships, they go through ups and downs. I’ve, over the last year, you know, have had some moments with my friends where perhaps I didn’t feel like the friendship was reciprocated or perhaps maybe I was a little bit more outspoken than I should have been. And we have these type of friendships where we can hold each other accountable, call each other out when something isn’t landing correctly. And I’d say there’s been two or three examples of me meeting with friends over the past year and a half where we met for coffee or maybe a drink and just hashed it out like adults and we’re able to share where we’re coming from. And more importantly, listen. Listen with intent. Listen not to be right or knowing when to debate or come back, but listening to understand.

And I think, were those conversations a little tough? Sure. But they were ultimately very grounding necessary and led to even stronger relationships. I’m totally happy with constructive criticism.

As mentioned, I’m a work in progress. There’s a lot I’m still figuring out as in this queer journey and in its lifetime.

And I feel like each of these potential roadblocks or conversations is helping me, helping my friends as well as we continue to live and support each other. There’s a great deal of maturity I find in these newer friendships and this chosen family I’ve made that is like truly beyond my wildest dreams. And something that wasn’t at all on my radar when I was talking about moving to LA and looking at the pool parties and stuff, I foolishly wasn’t on my radar. And now it’s, those are the type of relationships I crave.

[00:38:02] Michael DiIorio: Yeah, well said. And I want to ask you a follow up question to that because I think there’s a lot of people out there listening to this, hearing you, probably nodding their head, saying, yeah, yeah, I want that, I want that, I want that. Tell us, Pepper, what is one thing that you did to nurture this level of depth of intimacy with your friends?

[00:38:20] Pepper: Yeah, that’s a great question, Michael. Have you ever had like a friend crush on someone where you’re like, that guy seems great? Well, not. Well, that might sound different to gay men.

Let me, let me back it up. Like that feeling of I want to get to know you better. I feel like that can be perceived as like a pass at someone. But one of my closest friends, I remember seeing him out at a gay bar about like again a year and a half ago. I’ve been saying that a lot. I was like, I just told him, like, hey, like, I think you’re really cool. I’d love to get to know you better. And yeah, that could have sounded romantic, whatever. But I guess I took a risk and something I wasn’t comfortable doing when I was younger, to just tell someone, like, you’re really funny, you make me laugh. I would want to get to know you better. And that could have been received anyway, but it was pleasantly received and he reciprocated that. And he’s like, you make me laugh too. Let’s. I forgot what we did as our first, like, friend date. But just again, the vulnerability, putting yourself out there, reaching beyond the surface, just saying, I want to get to know you better is not something I had the tools to say or utter when I was younger. And it’s not, hey, follow me on Instagram. It’s let’s go out and tell me about where you grew up and, hey, when did you come out? It’s conversations like that that I think lead to sort of softening the barriers that we discussed earlier and eliminating those barriers that are in the way of fostering more genuine and authentic queer friendships. The putting yourself out there, it can be scary, and I’m not diminishing that at all. But you’ve actually taught me a lot about rejection and how to approach with respect and how to put yourself out there. So thank you for that. And it really does pay off when you find someone that’s willing to meet you halfway and have discussions that, again, go beyond the surface and still having those discussions about who are you dating? And, you know, what, are you listening to those more surface level things as well.

[00:40:22] Michael DiIorio: Pepper, you brought up such. Not to go back to barriers, but you brought up such a good point where those connections of, like, I want to get to know you better. Even for me, I’m speaking personally, like, sometimes my dick will get in the way and I’m like, oh, I want to get to know him better. But, like, I’m confused about how or. Or that part of me will kind of lead the way. And I have to very consciously put it back and say, wait, no, we’re. We’re actually looking for friendship here, which I’ve had to do in the past. But I think that’s a huge thing that we didn’t even touch upon, is that those blurry lines of the people that we want to have friendships with are also potentially the same people that we might want to have sex with.

[00:40:58] Pepper: Yeah. And that is tough. And, you know, not to air my girls tea, but in my friend group, there’s been, like, experimentation, if we will, and like, people have gone on dates, people have dated, people have hooked up, but just to see how that feels and, like, that’s going to happen again. We’re gay. It’s silly. And it goes back to communication, honesty and vulnerability. How did that feel? Is this something we want to explore? Do we have the same type? Or would we be wingmanning each other? If a group situation came up, would we touch each other? These are all not the most, I guess, comfortable questions, but now I feel super comfortable having those discussions with my friends. But it definitely took time to get there. And yeah, our dicks do get in the way. I’m A horny boy. I’ve mentioned it on this podcast all the time. I used to. My first episodes with you here were usually always about the more sexier topics. And that’s all fine and dandy and I’m happy to discuss them and we’ll continue to, but there’s a lot more going on.

And when we talk about vulnerability, vulnerability with our bodies and our sex lives is definitely on the table as well.

And navigating the. Again, the mind fuck of we’re friends, but I also find you cute. Do you want to fuck or is this just platonic? That can be challenging. Would never diminish that. I still get in my head about it sometimes, but it’s a work in progress. And I think being able to stop and ask friends, how is this going? Like, I know we’re, we’re good friends, but there’s an attraction there. I think you’re cute. You think I’m cute.

How is that feeling for you? Those are friendships or those are conversations I’ve had with one friend recently and we’ve known each other for two years. I have this one friend where it is a little bit of a blurred line because we’re super touchy feely and I’m not touchy feely with many people. So that kind of triggers something in me that’s like, oh, this is moving into more of a romantic situation, more of a romantic territory. But in having dialogue with this friend, we’ve come to understand that it’s just a comfortability we have with each other. And while we absolutely adore each other to pieces, there isn’t. We don’t see a romantic, a true romantic relationship here. It’s just a sisterhood and a comfortability.

And I don’t like cuddling with many people, but I will happily cuddle with him.

[00:43:21] Michael DiIorio: I was gonna say bromance. Then you said sisterhood. I love it.

[00:43:24] Pepper: Yeah, it’s a bromance, man. Absolutely.

[00:43:29] Michael DiIorio: Yeah. With my friends, it’s like, it’s a bit of a mix. Some of my closest friends are people that I’ve dated, slept with, and then we’ve kind of transitioned into friendship, which makes it very easy because we already have that base.

Others. Some of my closest friends, I’ve never even, like, there’s nothing sexual has even happened once. I. I don’t see them that way at all. Yet I love them. So I mean, that’s maybe one piece of advice I’d give is just be open minded to all the different.

You can stumble upon a gay friendship. It doesn’t always have to look like the way it might in the heteronormative world where you meet somewhere and then you suddenly like, hey, you want to be my best friend? That’s what it looks like on TV sometimes. And that’s never how that actually works in the gay world.

[00:44:09] Pepper: Yeah, I think just going off that, like you briefly mentioned, queer friendship can look and feel so differently. Like, there’s no need to compare friendships or think, oh, this is strange. Like, be open minded, like you said, and allow your friendships to blossom and evolve. And if things do take a romantic route down the line, great. And if they don’t, that’s great too. It just depends on that one on one interaction or perhaps two on one interaction as well. There’s a beauty and again, a silliness to all the connections that we can form in our community and to not limit ourselves into what’s expected or what’s heteronormative. And that’s something I’ve been thinking about too in the last couple years, is what I want my next relationship to look like. And that’s also something I’ve discussed at length with my friends and their experiences and what they’re looking for and what their comfortabilities are as well. It’s all helped me kind of reach my own conclusions and continue exploring what it exactly is I’m looking for in that realm.

[00:45:17] Michael DiIorio: Yeah. One thing that I would offer for anyone out there listening who has maybe, maybe you’re one of those people who has a lot of acquaintances and a lot of quote unquote friends, a lot of followers, if you will, but not many friends, is to trade those hundred acquaintances for like one or two real deep friends and go, go deep, not wide. Because it’s not, it’s never about quantity. It’s really about quality. And I know that’s such a cliche, but it’s so, so true. I, after Covid, for a variety of reasons, my friendship circle just shrunk. I think a lot of people did because of COVID But when everything came back, I was like, well, the ones that I stayed close to are still here.

And that says a lot. And then also I’m just getting older and who has time for all that stuff? And so like, I know seeing those images on Instagram of like, you know, 50 people at the pool party, you could think like, oh, yeah, I want that. And those people are all really good friends. But that’s not true, first of all. And also, I don’t think anyone actually wants that. I think we all Just want to be seen and understood and heard by at least one other human being on the planet.

[00:46:24] Pepper: Mm. That’s so well said, Michael. I’d say, like, five months ago, six months ago, hooked up with this guy, and then we started talking about friendships, and we know each other from the same volleyball league. And I told him that I was kind of struggling with keeping up sort of a vision I had when I first entered the league. And what I was sort of known for is being friends with everyone, which is great, and I like being a little social butterfly, but he told me that that just wasn’t sustainable. And when he told me that, I felt like, oh, maybe that was one of the reasons I, like, trauma. Bonded with this one kid I mentioned earlier who I didn’t necessarily enjoy our friendship with is because I was really looking for a place to find that connection and be able to have these deeper discussions. And I didn’t know where to pinpoint them because there’s so many options, but not options that were truly safe and options that would have been respectful and reciprocated.

And now, like, it’s my birthday next month, and I was just with one of these, like, near and dear friends yesterday, and he’s like, what do you want to do for your birthday? And I’m like, you know what? Like, this has been a really hard year. I kind of just want the seven of us to hang out at your place, if that’s cool, watch a movie. And that’s kind of all I want to do is nurture that chosen family, create memories together. It’s so cheesy. A few weeks ago, for another one of our birthdays, we made a little.

What’s it called, A bucket list for the year of things we want to do. And again, some of them were parties and concerts, but a lot of them were like, let’s go to a water park. Let’s go bowling. Let’s scrapbook. Like, what do you like doing? Like, some of them really like cooking. I don’t cook. I hate cooking. But, like, I’ll cook with them because it’s just about that nurture. And I’m really happy I’m in a place with them where I’d be more than happy to perhaps do something that’s not my favorite thing, but it’s about doing it with the small group of people that I feel 100% myself with and never, never judged for any part of who I am. So, yeah, when you go and talk about quality over quantity, that shift and that conversation I had with that guy from five months ago was really, really eye opening for me. That fact that it was unsustainable to be friends with everyone, liked by everyone. And that’s not to say I won’t be charming and friendly who come my way, but it’s about the intentionality and the preservation.

I found it really hard to make friends when I moved to la and I used to look at cliques and chosen families and like, they’re so elitist, they’re so exclusive.

And now that I’m in my own, I don’t think we ever do so in a true exclusionary way. But now I kind of understand why sometimes it may be hard to infiltrate. I guess those groups is because it is tough.

It’s tough for a number of reasons. We talked about so many barriers so far that when you find it, you kind of want to hold on very, very tightly to it.

[00:49:23] Michael DiIorio: Yeah. And I think that’s another big pain point that I’ve heard of, is people wanting to like, New York is a great example. New York, these big cities, London. I hear this a lot from gays in big cities. Like, they say, the city’s unfriendly. There’s all these guys, but everybody just wants to fuck. Not many people want a relationship or they’re always looking for the next best thing. And there’s all these guys. But no one is really interested in making friends after a certain age. Like after you get out of school and when you’re an adult, it’s really, really hard to make friends. So this podcast has dedicated so, so many episodes to friendship, how to make friends, friendships for introverts, friends with benefits, friends with intimacy. We have dedicated like a lot of episodes to this topic for good, good reason.

[00:50:03] Pepper: Yeah. And I think one of the posts I’m most proud about the last year was something along the lines of, you mentioned competition. And there was a post I had that’s like, what if gay men transition to collaboration over competition?

So one of the posts was, instead of being like, oh, he looks like he has such great friends in this amazing little clique, instead of resenting that guy that you’re friends with, perhaps approaching him, like, I approached one of my friends last winter and said, when I said I’d love to get to know you better, you can approach him and say, you look like you have an amazing group of friends, would you mind introducing me? And yeah, that could be really nerve wracking. But it’s about that, putting yourself out there and searching for those friendships that can become, you know, more profound and intimate.

[00:50:51] Michael DiIorio: Yeah, I love that collaboration over competition is kind of what we were talking about as well. Like, it’s like collaboration over competition for all you guys who love alliteration like I do. And you want friends, not followers.

[00:51:01] Pepper: Yeah.

[00:51:01] Michael DiIorio: So take those two lovely little nuggets of alliteration from this episode. Pepper, anything else you want to say before I wrap this up?

[00:51:08] Pepper: Thank you for having me. I’m always happy to be here. Make sure to follow the gig.

[00:51:12] Michael DiIorio: Good.

[00:51:13] Pepper: I never mention. So follow the giga.

Yeah, you do it for me. So thank you. You are the one growing my platform.

And for anyone that’s watching this or listening to this and perhaps feeling a little behind, please know that I know I’m speaking for both of us here. We have felt that, too. And it’s taken trial, tribulations, ups and downs, failed friendships, successful friendships to get to a place where we’re comfortable speaking about this, where we’re coming to a place and can more easily pinpoint red flags and green flags in friendships. So go at your own pace, please. Don’t be too hard on yourself, as I am always hard on myself.

And if you’re ever feeling behind as we started this episode, trust me, you are not alone in that feeling.

And keep pushing, keep putting yourself out there. You’re as cheesy as it may sound like your people are there. And there’s so many other places to find queer friendship than the scene or the gay bar. There’s recreational sports. I met most of my friends who are volleyball league. That has truly changed my life.

There’s the gamers. You can find friendships at performances, book signings, volunteering.

Don’t limit yourself as you put yourself out there. And as usual, I just wish everyone listening a very, very happy day. And this is coming out, I believe, May 29, you said so. Happy pride, baby. Happy pride to everyone listening.

[00:52:41] Michael DiIorio: All right, thank you, Pepper, for that lovely little closing moment there. Thank you, Pepper, for joining us today for. I don’t know, I can’t even keep track anymore, I think. Seventh time at this point. Sixth, seventh, something like that. So thank you for coming on here today and telling us about your friendships and what you’ve learned. I want to thank our listeners and viewers for sticking with us for this episode. And remember, if you’re watching us on YouTube, please tap that thanks button to show us some love. If you’re listening on Apple Podcasts, don’t forget, you can subscribe on Apple Podcasts to get early access to episodes before they are released to the general public. All of your support helps us to make content for you guys and supporting our community. And remember, guys, just like Pepper was saying, if you want to find some connections outside of the usual gay bar situation, please do check out our events within the Gay Men’s Brotherhood. We have events every single Thursday, so we hope to see you there. All right, guys, have a great one. See you next week, Sam.