Dating as a Gay Man – Advice from a Matchmaker

Gay dating advice: a guide on finding love, navigating differences, and building connections.

While I’m happy to work for people of all walks of life here at Tawkify, I spent the very first few years concentrating exclusively on matching gay men. I’ve worked for gay men of every shape, color, age, and net worth across the US, and I’ve learned a lot. I’ve observed trends in thought and behavior, how they might relate to the generations to which we belong and how they’re informed by our experiences. We grew up different. We remain different, in some way, from our straight peers, and our approach to dating is no exception. It’s through my work with my clients that I’ve learned to be very grateful for being queer. I feel lucky to say that I would not have it any other way–words that would cause a 17-year-old me to shudder.

While the world slowly becomes more accepting of diversity, in what feels like a three-steps-forward, two-steps-back, awkward waltz, we’re forced to dance along. I’ve written down a few steps that I hope will help you or a friend on your own journey. As a note: the bulk of these take-aways have been informed by work with cisgender men who identify as gay, but you may find at least some overlap with other iterations of the LGBTQ+ or gay dating experience.

Shifting Paradigms in Dating

A quick Google search on the decline of gay bars will provide you a lot of context as to how LGBTQ+ community spaces are changing, and may empower you with some knowledge of older times. A quick distillation of this shift will tell you that rising social integration and a sea of phone apps and digital platforms have rendered hubs for queer social gathering less essential for finding a partner. Whether you view this as progress or a major loss may be influenced by your generation group and what you’re used to. In either case: you’re more likely to meet someone online these days, and products created for LGBTQ+ dating specifically have provided us safer spaces than ever before to connect with others, whatever your pronouns may be.

When you’re putting yourself out there and ready to find your person, as a man dating men, there are a few considerations we thought to talk about.

Being Different

One of the most terrifying and empowering things about living romance and exploring love as a queer person is that the road hasn’t been paved for you. Every experience is different, but many of us are not as securely fettered to the conventions of our straight grandparents, and while you may encounter more traditionalist views on concepts like monogamy and how “straight-presenting”/”traditionally masculine” people choose to show up (or date), there are indeed lids for every pot in this community. You have the opportunity to define your own values from scratch, and when you marry that with truly dating with intention, it’s a potent mix.

Intersectionalized Gay Men

While the concept of intersectionality has been around awhile, it’s only more recently come into the modern lexicon. If you’re unfamiliar, consider it an overlapping of marginalized identities in one person. Many of my clients of color, for example, grew up in a white-centric society and a heteronormative home, nursing feelings of discomfort or moments of rejection essentially everywhere. Whatever your history or identity, our coming out stories and experiences may have influence on how we build intimate relationships, and knowledge of that can be helpful, especially when dating people who have had an experience unlike yours. A note on this: I don’t recommend discussing coming out experiences on a first date. Many of my clients have cited using this as a conversation starter, but for many, this was a difficult period in their lives, and some may not have come out much at all.

Accepting Identity

We encourage dating people whose values align with yours, whatever that means to you. I will say that the conventional position that being “totally out” to everyone is the only way to live a free and actualized life is based on a number of presumptions. Our cultures, nuanced relationships, and personal preferences play a huge role here, and a little patience might go a long way if you find someone who wields their queerness differently than you. 

Finding Mr. Right

We recommend being open-minded to the idea that your prince charming may arrive in different packaging than you expect. It’s valuable to know what you like and need, but when defining your qualities of a good partner, consider making sure your list of non-negotiables vs. preferences aren’t in your way.

Sexual Dynamics

You might not have to look hard to find sex positivity in the queer community. Your dating expectations are your own to define, but I do have some anecdotal context to this. My composite conclusion from living as a young gay man in New York City and hearing from my many clients from around the country is that if you’re dating with intention, it might be worth it to hold off on sex. At least for a bit. The first date?

…a moment?

The rapid availability of partners, especially in major cities, might make it challenging for us to invest. You may feel more comfortable giving something a real shot once you’ve established an emotional bond with someone, first. If you’re reading this and have been on at least one great first date that ended the next morning, only to never see him again (whether by his hand or yours), give this one a go.The good news is that if you do see clear signs of compatibility, and you give it a little room to breathe, it could be even better later!  

If you’re not apt to delay intimacy and prefer more freedom in this area, you’ll get no shame from us. It’s worth it, though, to arm yourself with some information on steps you can take to stay safe. An open conversation with a doctor about your lifestyle might be helpful to identify whether PrEP and or DoxyPEP might be right for you to prevent the transmission of infections. Additionally, medicine has come a long way, and stigma over HIV infection in our community can be remedied with information. If you haven’t already, consider reading Undetectable=Untransmittable.


I’m happy to report that all this paranormal activity isn’t unique to our world, but it is ours too. Our take? You are entirely capable of avoiding breadcrumbing or a sudden disappearance on someone investing hope or energy in you. It’s hard to tell someone you’re not that into them, but it’s kinder than the alternative. What’s very good to know, and please remember it if you yourself encounter a ghost: it likely has a lot more to do with what’s going on with them than anything to do with you. 

Generational Divides

I’ve been intrigued much of the time in observing some of the generational differences in our community, and how they manifest in ways you might expect. We’re not defined by our environment, but we are informed by it. A twenty-year-old male figuring out how to love other men might come to different conclusions through the ages, and for a number of reasons. Our cultural landscape and level of social integration as queer folks are observably different when assessed comparing an era of the Stonewall Riots, and era of the AIDS epidemic, an era of the Matthew Shepard and James Byrd, Jr. Hate Crimes Prevention Act, or our current, digitized world, enriched further by open social discussions of sexual and gender fluidity. When you’re out there dating someone older or younger, it’s worth zooming out for a second to consider their experience (and ask questions!) as that context might make it easier to foster real connection.

Get Started Toward Your Last First Date

Try Tawkify today. We only accept candidates we believe we can match.