Gay Men’s Dating: What Your Dates Aren’t Telling You

Gay Men’s Dating: What Your Dates Aren’t Telling You

It’s been a long time (32 years in 2024) that I’ve been a gay men’s specialist psychotherapist (California),  AASECT Certified Sex Therapist, and life/career/relationship/sex coach (worldwide).  In that time, I’ve worked with hundreds of single gay men who share the rewards and challenges of their dating life, and I’ve coached many guys on how to date successfully, and even to be a better sexual partner (although sex therapy is still “talk therapy;” it’s not sexual surrogacy or any physical contact – that’s different).  And, of course, hundreds of gay male couples and polycules over the years.

I’ve had to be tough sometimes.  I have a saying that the older I get, the stronger my opinions get, because I see gay men doing the same things over and over that self-sabotage and generally fuck up their lives, and, fortunately, I see the same strategies work, over and over, that very reliably make your life better, personally and professionally (isn’t it great when things work?).  That’s my job; that’s what gay men hire me for.  Providers like therapists and coaches can never ethically make “guarantees” for an outcome, but we can share what we’ve seen work for many other guys over time.

Gay men come to me with a lot of dating complaints and frustrations.  Being single is not really easy for anyone (just ask single straight cisgender women), but there are unique challenges for gay men as sexual minorities in society.  To find the right partner – and guys do it every day, despite all the challenges – you have to have some combination of luck and skill.  There’s not much you can do about serendipity and luck – that’s up the Fates or the Universe or God or whatever – but you can help your skills.  Sometimes, you’re the last one to know that you lack certain skills that – if learned – would help your dating success.  And, you really don’t want to be the last one to know.

Guys often de-brief with me about their past week, since their last session, and they report back to me how their dates went.  And, they aren’t shy in sharing what they did not enjoy about them.  I wanted to share, here, some of what I hear them telling me about their dates that they certainly are not frank enough to tell them.  Let’s look at some that I hear, in no particular order:

1. Chatty vs. Listener – It’s just human nature and part of our ego that we like to be listened to, validated, and admired. There are times when, actually, flattery will get you everywhere (especially on a second date, or in bed).  You don’t want to be that guy that, perhaps out of nervousness or social anxiety, talks too much about himself.  It’s such an easy pitfall of dating to fall into.  If you talk too much about yourself – either about what you are, or have, or earn – you’re going to turn off your date.  Same thing if you complain too much about society, your job, your family, and certainly your exes.  If you’re going to talk about yourself, speak about your passions, what brings you joy, what amuses you, what gives you pleasure, what you’re rewarded by, and certainly what excites you.  Excitement is contagious and makes you charming; bragging – even “humble bragging” – is not.  You don’t want to be that guy that when your date goes home, and he’s asked about his date (with you), “Oh, my god, that guy just would not shut up.”  He’ll never tell you that – but he will tell his roommate or his friend or his therapist that, and you won’t hear that.  In fact, you won’t hear from him again – especially about having a second date.

2. Kids – I’ve written before about when you’re in a relationship as a gay man, and one of you wants kids, and the other doesn’t. But it’s best to avoid the whole kids topic on a first date.  If you bring up kids too early in the dating process, it tends to make your date feel smothered and obligated, like you’re trying to force him to commit to big life decisions (with you) drastically prematurely.  Even if you know you’re dating because you want to find a partner and also co-parent with them, that’s a topic for discussion further down the line after you know there is a strong foundational relationship there.

3. Ambition – This one is tough, because it’s about balance. If you don’t have enough ambition, if you appear lackadaisical, lazy, and goal-less, it’s a turn-off.  Your date worries – even unconsciously – that you’re going to be a mooch and he’s going to have to support you on his salary – low or high – while you languish and fail to really launch professionally.  That isn’t sexy.  Having – and discussing – some dreams and goals, however short-term and realistic, or longer-term and challenging – is good.  Not knowing what you’ll do in Life past this weekend’s parties is not.  But, similarly, being Mr. Log Cabin Republican and bragging about how you are – or have – made your first million dollars because you’re just “all that” – especially in a way that reveals that you ruthlessly exploit others – is a turnoff.  So much of dating is about balance between two extremes, and that’s what makes dating hard – it can feel like a tightrope walk.  The key here is discretion and balance.  And you can’t always gauge how you’re doing by their reactions, because even if they can’t stand you, they probably won’t show it on your date.  You just have to live with the ambiguity that they may, or may not, be enjoying this.  You’ll know they do if you find yourself on subsequent dates.

4. Closeted – Dating a closeted guy can have a certain naughty “hotness” to it, such as the idyllic affair with a straight guy who is married. But, this gets old fast.  The annoyance of his having to do somersaults to avoid being “caught” by his wife or his kids or his work obligations gets old fast.  Plus, it’s very invalidating to you as a gay man to be treated by someone else as their “dirty little secret” they “have to” (which is B.S.) hide.  And being told he’s going to “come out soon” and leave his wife or parents or whatever almost never happens in reality, because he’s too comfortable (emotionally, financially, and socially) with the status to risk all that, even for you.  He wants both the life of Heterosexual Privilege and he wants dick – and while that might be great for him, if you want a serious, adult, romantic and domestic relationship, you will never find it as long as you’re wasting dating time with Mr. Closet Case over here.

5. Douching – Most guys will never say what they really feel about sexual situations, but they are thinking it, and they will probably talk about it later, just not with you. Problems in both oral and anal sex are definite dating pitfalls.  Using your teeth when you’re performing fellatio.  Not swallowing and being a spitter.  Not douching as a bottom and giving him a little something “more” than he was expecting or asking for.  Sure, some “hygiene accidents” can happen in sex, and gracious gay men understand this and move on, but you can certainly do your part to prepare, that if you’re going to bottom – or even if there is a reasonable chance you will – attend to your sexual health by performing a reasonable (not excessive!) anal water douche, take your fiber, and watch your eating so that you’re not with diarrhea or gassy on the night of your date, if possible.  Lots of resources about sexual preparation for bottoming are out there; use them.  Lots of books on better oral sex performance are out there (one is “Blow Him Away” by Marcy Michaels), too; read them.

You also don’t want to be the “lazy” lay who just kind of lays there and says, “do me; I’m beautiful.”  You want to be an active, enthusiastic (not “spastic”) participant in the action, that is hopefully varied (see my previous writing on “being a better lover.”) You can be verbal and “into it” but you don’t have to wake the neighbors, or, these days, your seven roommates that it takes to make rent.

You want to be skilled in oral, anal, manual, and lots of sexual techniques that you can cultivate over time, including possibly kink play and its various equipment; get coaching if you have to.  But you don’t want to be that guy who is labeled the “bad lay” for whatever reason after your date debriefs with others later.  (Plug:  I’m going to be offering a new online course, “Gay Men Improving Sexual Self-Confidence,” available on the Thinkific.com platform, shortly, after the finishing touches are put on that.  I’ll be announcing that in future blog article, podcast episode, or Instagram post.)

6. Bad Breath – I hear this one so often, and it’s so simple. You’re going to be close to a guy, kissing him, with your mouth front and center.  You want to make sure that mouth is a clean, fresh, pleasant environment to be “this close” to.  Consult with your dentist if you have concerns.  Practical steps like brushing your teeth, using mouthwash (or strong mints after dinner), flossing your teeth, using a WaterPik, scraping your tongue (that’s a huge one), and avoiding certain spicy foods (garlic being the classic one) are all good tips.  Even asking your date, “Hey, I ate onions on a burger at lunch earlier; do I need a mint?” and let your date tell you if the answer is yes.  If so, just excuse yourself and do something – retreat to your bathroom – or even his, at his place – and use the mouthwash or even his toothpaste (not his brush, or course) and do a quick freshen-up, then get back to the business of making out as foreplay.

7. Nails/Nose Hair/Ear Hair – If you don’t notice in the mirror what’s happening before your date, your date will notice it an hour later on the date. Look down.  What do your nails look like?  Dirty nails is actually a complaint I hear about casually often.  Bitten nails are not ideal, but somewhat forgivable; everybody is anxious these days.  But clean them with a basic manicure kit you can get at a drug store.  Take a look slightly up in the mirror and assess the nose hair situation; the older you get, the faster it grows.  What about your eyebrows?  If you’re young, they’re probably “on fleek” (as the Internet influencer coined) and probably fine, but if you’re older, you can get scraggly single hairs that need trimming.  Check your ears; if you’re younger, they’re probably fine, but if older, you can get odd little hairs there that look better shaved off.  Even if your look is overall edgy, a certain basic neat-ness mirror check before you leave home for your date is always impressive.

8. Sports – Gay men can go either way on sports. Some like not at all, some like a lot (how butch), some like some but not all, some are nonchalant, and others are raving super-fans.  Discretion on dates might be to ask your date about his sports interests, and leave it alone if he has none.  And if he has some, even if you don’t, it can be validating for you to listen to his interests and let him share his enjoyment of them.  Like any topic, even if you don’t share the same interests, he’s going to like you if you’re willing to listen, and you get to share your interests, too.  Ideally, you have some in common.  But even if you don’t share his level of (fanaticism) enthusiasm, it can be charming for a guy to talk about what he loves.  Don’t yuck his yum.

9. Femininity – It’s a pitfall to say that “more masculine” gay men are superior to more feminine gay men. It’s such misogyny in general against anything that seems “womanly” (whatever that means) and it’s misandry in the idea that men can’t be themselves, whatever their style of expression or personality or demeanor is.  Butch men are not superior men; they are just butch; femme men are still men, unless anybody is identifying as trans or nonbinary.  These days, it’s especially important to validate someone’s identity; gender role enforcement rage (I’ve written on that earlier) is just passe at this point.  But how butch-femme you are, on a spectrum, might be a point of compatibility in dating.  Something to keep in mind, but don’t be someone you’re not.

10. Belly – We want to get away from the old days of Adonis Complex and Body Fascism and all that, but right or wrong, I do hear guys (many, over the years) either appreciate an athletic physique or criticize overweight, obesity, or “belly.” While some guys specifically like “Dad Bod,” others do not.  You can avoid any guy who doesn’t have eight-pack abs, but you might be lonely doing that, especially in the long-term (today’s eight-pack abs are very often “Santa without padding” in about 20 years, if you’re lucky enough for your relationship to last that long).  It’s a stark reality that gay men do tend to like a muscular or lean physique, which is why gyms and trainers are a multi-billion dollar business, even with just gay men, worldwide.  Decide what’s right for you – both what you are, and what you like – but accept that body shape preference is going to be a variable in dating.

11. Messy Place – You don’t have to be Architectural Digest in your home, but if your date sees where you live, you can at least take care of the basics. Before a date, if you think you might end up at your place, or if he’s picking you up there, or even if you’re having him over for dinner and “Netflix and chill,” take a look around.  What would a potential visitor be turned off by?  Is there pet hair on your couch cushions?  Is there any trash around that needs to be thrown away?  Is there anything cluttering that needs to be put away?  Is something dusty or smudged or stained that could benefit from the quick application of some cleaning supplies like Windex or Formula 409 or one of those?  Are there outdated magazines stacked too high? Are all of your clothes put away? Is there any lingering scent from last night’s dinner in the air?  Is the bathroom mirror clean?  Is the toilet free of drip spots?  Are the trash cans reasonably emptied, including in the bathroom?  Like it or not, if your place is messy at all, your date will notice, and it will lower his impression.  Even if you can’t afford expensive furniture or appliances or devices, or even if your place is older, with older carpeting or drapes or window treatments, you can still make the most of what your place is.  And if he’s going to be mad because your furniture isn’t designer and new, then there are more problems going on than that.

12. Pet Behavior – Take care to think about how your pets behave, if you have them, when your date is visiting. If you have a dog that barks a lot, or jumps up on people, try to control your dog; your date doesn’t want pet hair all over his black jeans.  Or if your dog is being distracting with noise or hyper behavior.  Or a cat that likes to jump in people’s laps and possibly snag is new sweater.  Or a boa constrictor who wants to get really close (kidding!).  Sure, you love your pet, but to your date, it’s a new thing to get used to, and he’s there to date you, not your pet.  Put pets in another room if you go to bedroom together.

13. Negative Content – In conversation with your date, be careful of the classic “red flags” guys say on dates that turn off your date. Talking shit about your ex, complaining too much about your job, emphasizing your insecurities or flaws, or the opposite of bragging too much and alienating your date with your “impressive resume recitation”, or criticizing whole groups of people (ethnicities, races, national origin, disabilities, etc.) are all no-no’s on dates in terms of the content of what you say.  When in doubt, ask him about himself – maybe where he’s from (although that might trigger bad memories, if any, from his Family of Origin), what he does for work (although he’s “off the clock,” so careful there), and certainly a safe area is asking what he enjoys – from movies, to TV, to sports, to books, to crafts, to any kind of pastimes.  People like people who ask them to talk about the things they like, even if you don’t like the same things.  Let him express his joy of what he likes to do, especially the dorky things like comics conventions or video games you’ve never seen.

14. Behavior to Others – Guys will complain about their dates they just had if the date treats others badly. Certainly, being polite to server staff, valet parking attendants, coat-check staff, restaurant host/hostesses, theatre ushers, parking attendants, the people at the next table, running into people you know in public, etc. are all going to be interactions that he’s observing and possibly judging you on.  Introduce him if you run into friends of yours inadvertently.  Even how he drives and treats other drivers is a factor, especially if he’s driving aggressively or takes up two spaces parking.  It’s always good to be polite to others, but on a date, it’s especially important.

15. Money Miserliness – If you really can’t afford to “treat” your date at dinner or the theatre or something, be up front. You can explain that you’re “having a tight month” and suggest that you split the dinner bill or the cost of tickets (although you might mention this before the date), or suggest that you’ll “get” the dinner tab and he “can” get the movie tickets, something like that.  It’s so cliché to do this stuff like “oh, you should pay for everything if you ask someone out,” and it’s outdated.  A lot of people today – especially young people – cannot afford to pay for cocktails, dinner, dessert, tip, parking, movie tickets, movie concessions, etc. all themselves, or they couldn’t go out very often.  Just be up front.  But also understand the “cost of doing business;” if he invites you to his uncle’s cabin at a ski resort, offer to “cover” something; don’t just sit there and be treated for everything. Even if you don’t make much money, or as much as he does, there is always something you can spend on – buying snacks at a gas station on the road trip, or buying some groceries for breakfasts at the cabin.  You don’t have to over-extend, but you also don’t want to be stingy or entitled, either.  Most people will know the difference.  If you ask a guy out, and he works as a server at a little coffee shop and you’re a CPA, don’t ask him to split the dinner bill at a four-star restaurant.  Cover dinner and tip, and then if he offers to pay the valet parking tip of $5 or whatever, let him do that.  Be aware of the relative proportion of your incomes (which I’ve written about before, “income disparities in gay men’s relationships”).
16. Tentative Tops or Bottoms – If things progress to sex, give him a good time. It all has to be consensual, reasonably safe (discuss things like PrEP and/or condoms, etc.) But lots of guys complain to me about guys who are “tentative” tops or “bump on a log” bottoms.  Be into it; be enthusiastic.  Don’t violate your own boundaries, like agreeing to something that is painful, unsafe, or triggering, but it’s OK to get “into it” (my articles on “Overcoming Fear of Topping,” and “Overcoming Fear of Bottoming” might help with this).

This isn’t an exhaustive list on how to stave off or prevent your date griping about you later to their roommate or their friends, but it covers the basics.  You can’t account for everything in attraction, chemistry, personalities, culture, values, etc., but part of being the good lover (I’ve written on that before, too) is also being the “good date,” and if you cover these basics, you’re much more likely to make a good impression and for both of you to have a good time – and, a second date!

If you would like more customized help that is specific to you and your situation, consider booking an appointment for psychotherapy (for guys in California, where I’m licensed for that), or Coaching, anywhere in the world (we just figure out the time zone difference when we schedule appointments).  There are some areas of overlap in those services, but also some important legal and ethical differences that are important to differentiate between these types of professional services; see also GayCoachingLA.com for Coaching services.  I can also answer any questions you have about this.  See also other Blog articles on this website, or check out my Podcast, “Gay Therapy LA with Ken Howard, LCSW, CST” heard in over 148 countries around the world, with over 150 episodes to date.  I also offer online courses, including one on gay men starting your own business, available on the Thinkific course platform.  Other online course offerings are in the works, including the upcoming “Gay Men and Improving Sexual Self-Confidence.” If you have suggestions for future blog articles, podcast episodes, or online course topics, your suggestions are welcome.  If you want individualized help sooner, email Ken@GayTherapyLA.com, or Ken@GayCoachingLA.com, or call/text 310-339-5778, and I’d be happy to help.  (Instagram: gaytherapyla)