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Phil is here to help you through your loneliness and get the

soul-nourishing connection you need and deserve

Dating as a gay man: how Angello worked through loneliness to find real connection

Updated: Jan 24

Did missing out on dating men

when he was younger feed

Angello's loneliness?


Very few gay men seek out and then read articles about loneliness unless they’ve come to the realisation that they’re lonely. The stigma and shame we feel is real, and it takes a lot of courage to even engage with the subject.

I’m proud of you for opening this article. I recognise and admire your courage. Now that you’re here, let’s start getting you connected to yourself, those most important to you and to your community.

This is the next article in an ongoing series where we're exploring loneliness as a lived experience from others in the global gay and queer community. If we are to de-stigmatise gay loneliness, then we must know that there are other gay and queer people thinking experiencing loneliness like we are. I'm here to have The Loneliness Guy as a forum for that to happen.

Enter Angello Floresco. Angello is a Vancouverite and a follower of The Loneliness Guy on Instagram. Angello and I have been chatting about his loneliness and his reflections on it. Angello shared that he has been reflecting on feelings that he missed out on many firsts when he was a teenager growing up gay in a time when same-sex dating was not something anyone did.

I know that this is an experience that resonated with me and would resonate with many of you, too. I asked if he'd be open to sharing his experience on this blog and an upcoming episode of the podcast. It felt like he said yes without hesitation. You're about to read his words.

I've not changed a word. I want to honour Angello's courage, curiosity and his beautifully human story.

Before we go on, this article was published on Ngunnawal country. I wish to acknowledge and respect the Ngunnawal people’s continuing culture and the contribution they make to the life of Canberra and the surrounding region. I would also like to acknowledge and welcome other Aboriginal and Torres Strait Islander people who may read this post.

~ Phil

* * * * *

I grew up on the west coast of Canada to religious Eastern European parents. Although they were Orthodox, they figured it would be a good idea to keep me within the sphere of Christianity and they enrolled me in an all-boys, sports-focussed Catholic school. I was, of course, different, and always wrestled with loneliness because of this “difference”. In elementary school I made the mistake of bringing my She-Ra dolls to school. That story followed me for years, and it didn’t help that I was at the same school for all twelve years.

As a younger teenager, my group of friends was limited, and I spent a good portion of my time in front of the TV either obsessing over Madonna videos or playing video games. Those were my main forms of escapism!

Further into my teens I did try to socialize more. I gained more confidence in myself when I started working in a restaurant, and my social circle expanded beyond what I was exposed to at school. People actually liked talking to me, thought I was funny and fun to be around, and these were the types of interactions I didn’t experience in my school setting.

I tried my hand at dating girls because that's what I was supposed to do. This never led to anything meaningful: No emotions, no first kiss, no hand holding, no butterflies. I was certainly curious about how it felt to have those feelings, and seeing romantic, “first love” teenage movies almost reinstated my loneliness.

In my graduating year I felt something for another man… but I didn’t know what it was until I actually came out years later. He was my teacher. He ticked all the boxes of things I now find attractive in men: athletic, intelligent, articulate and he was nice to me. I couldn’t understand why I thought of him so much and why I felt excited to go to his classes. Looking back I realise this was my first crush, but I never understood the feelings back then, so I never acted on it. I wonder if this situation in my past set my behavioural patterns up for adulthood: Keep a low profile, don’t trust your feelings, it won’t be reciprocated.

When I was 20, I lived by myself in Japan for a year as an English teacher. I had a chance to live on my own, away from my family and really learn more about myself. Navigating yourself through a foreign country where you don’t have a good handle on the language puts you in a forced position of self-discovery. After coming back to Canada, I started going to gay clubs more and more. The great music lured me in but the feelings I felt kept me coming back. I finally came out when I was 20 and my parents weren’t too happy about this. It was a very rough time for me and the relationship with my parents broke down several times before finally getting better.

Going through my 20s, I finally met up with my tribe: DJs, drag queens, performers, and gay men. Yes, I was having lots of sex, but more importantly I was kind of living the chaotic life that a teenager would. I didn’t have a lot of social interactions as a teen. I even did drag for a number of years to feed my need to entertain others and connect with them through performance.

During my 20s, I wasn’t facilitating my needs for intimacy because I was having too much fun not thinking about it.

Into my 30s, I started to move away from club life to focus on my career and my relationships, but dating was incredibly hard for me. My identity as a performer wasn’t the biggest secret in the world. I also was able to live out my childhood dream of collecting toys and dolls from shows that I grew up with as a kid and young adult - Jem, She-Ra and Sailor Moon. Those were my superheroes!

I was typically subject to criticism from guys I tried dating as I wasn’t masculine enough. This seemed to be a barrier for me as I tried to navigate the dating world. It got to a point where I believed something was wrong with me because I was single. I believed I was unworthy, undesirable and unrelatable.

I had a very hard time with this for a while and it took a series of heartbreaks for me to realise I was in fact doing something wrong: I was looking for a relationship and intimacy to validate me. I wanted to have a boyfriend as a sign to the world that I was worthy. It’s like I wanted to have a relationship to show the world how cruel and wrong they were to make me feel unworthy.

So while I was experiencing loneliness, my motivation for trying to remove this feeling was poorly aligned.

I needed some more time with myself to appreciate what being single is, and also not fall into the trap of being a serial relationship seeker.

Now in my mid-40s, I feel like I’ve addressed and accepted my single life. Although I may be a bit too guarded, I am pushing myself out there again, to at least experience life instead of running away from it.

Recently, I’ve come across the Netflix show ‘Heartstopper’. It’s a great show, but it has really opened up some thoughts about me and my development as a teenager. I really do love seeing a story about two teenage boys navigating their feelings and eventually finding love. I hope more younger boys can explore their feelings more easily, with the support of their parents and peers, without the fear of insults or violence.

It’s my sincerest hope that it gets easier and easier for the gay men that will follow me. I hope they get a fair chance to really explore their emotions and feel love and not reduce their first encounters to something physical only. Watching this show though makes me wonder how my life would have been different if I was openly out in my teens. Would I have intimate conversations with other guys? Could I explore my feelings without fear and enjoy those types of moments I saw in the movies? I find dating a challenge, as I’m sure it is for most people.

Some part of me feels my teenage years were “ripped off”, or missing, because I was too afraid, and knowledgeable of what to do with myself.

I don't want this lack of life experiences to affect my entire life, however I’m curious if other men my age have been in a similar situation and have the same thoughts. I’m in a good place now, but I’m hoping more conversations will help me navigate these feelings better.

* * * * *

Angello - an ENORMOUS thank you to you for sharing your loneliness story with us. It's always a privilege to receive someone's loneliness story, and I greatly admire and respect your courage.

Reader - you may need some help after reading this article. Please, reach out to your partner, a friend or someone in your orbit who you know is trying to put themselves into the world just like you are. That could be me through my mentoring services. That could be a therapist or a counsellor – including a crisis counsellor. That could be a coach. It could be a combination of all.

Be sure to check out this page when you need help.

Let's have a chat with Angello about this beautiful article. Join us for a coffee and a chat in the upcoming episode of my podcast for gay men ‘Connection over Coffee with The Loneliness Guy’ from Thursday 18 August 2022.



Important notice: All views expressed above are my own/the authors and are intended to support, challenge and inspire gay men to consider the issue of loneliness and increase awareness of the need for authentic connection with themselves, with others and their communities as an antidote to chronic loneliness. They are not intended to, nor should they, replace the advice of a licensed helping professional. Please consult the Services page if you feel that you need the services of a licensed helping professional where you are in the world.


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