Biggest Mistakes Gay Singles Make On First Date

Gay Dating

7 Biggest Mistakes Gay Singles Make on the First Date

Mason Glenn

Written by: Mason Glenn

Mason Glenn

Mason Glenn has had a long career in the matchmaking industry and has spent his time helping high-caliber clientele in Los Angeles select eligible matches. He specializes in working with gay men.

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Edited by: Lillian Castro

Lillian Castro

Lillian Guevara-Castro brings more than 30 years of journalism experience to ensure DatingAdvice articles have been edited for overall clarity, accuracy, and reader engagement. She has worked at The Atlanta Journal and Constitution, The Gwinnett Daily News, and The Gainesville Sun covering lifestyle topics.

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Throughout my professional dating coaching and matchmaking career, I’ve noticed many bad patterns in terms of singles’ behavior, and a lot of the time, they don’t even know they’re behaving this way.

In case you keep missing the mark on your first dates, I’ll walk you through the biggest mistakes single gay men make when they initially meet someone they like. I’ll also share my top tips to avoid these mistakes from here on out.

1. Not Knowing Anything About Their Date

Do your research! There’s a reason why you want to go on a first date with this person, so take it seriously. The most desirable men are the ones who take that extra step to make positive and lasting first impressions.

Did the guy write something in his dating profile that stirred your interest? If so, remember it and bring it up on the first date. Showing that you took the time to learn about him and come up with some conversation ideas will keep the date flowing and fun.

And be prepared to share stories that show how unique — and maybe even weird — you are, too. Weird is always more interesting than you explaining that your favorite hobbies are going to brunch with friends, working out, and being outdoors. Please name a gay man who doesn’t like to do those things, in general.

What TV shows are you currently watching? What movies are you looking forward to seeing this year? What concerts do you plan to go to once things fully open up? Where is your next vacation destination? Sharing this kind of information will allow your date to get a glimpse into how you define your adventurous side.

2. Hooking Up Without Realizing Their Date’s Expectations

Gay men are notorious for hooking up after the first date. I get it. It is what it is. However, if you want to be in a relationship, but you keep hooking up on the first date and then things fizzle out, it may be time to recalibrate. Sometimes it’s best to wait at least until date number two to hop into bed with someone.

Photo of a gay couple in bed

If you want a relationship, hooking up on the first date won’t serve you well.

Sometimes gay men just want a sexy guy to have dinner with and sleep with at the end of the night. Sometimes this song and dance is for just one evening. Did you understand this expectation, or did you have an assumption that left you confused when you didn’t get what you wanted?

It’s important to set these ground rules even when you first hit someone up on your favorite dating app. This often keeps you more honest and feeling less defeated if some wires were crossed. When in doubt, be forward in your communication. Most gay men appreciate forthrightness rather than you playing nice or being ambiguous.

3. Being Late and/or Noncommittal About Availability

It’s never good to start off with an apology when meeting someone new. If time management is an issue of yours, address it before you start dating. There are plenty of articles on the value of being punctual you can read and online classes you can take.

When I was more single than I am now, I would rarely go on a second date with someone who was more than fifteen minutes late to the first date. I made an equal sacrifice to be on time, and all I expected was the same respect. Sure, if traffic was a little bit more than what my date expected, I totally understood. However, with so many ways to anticipate traffic these days, my issue was how could my date not know he was going to be late before he left his place? I was less forgiving then.

It was always refreshing to me when someone would suggest a specific time and place to meet. I always appreciated that gesture, and I would often reciprocate. This would normally lead me into second date territory.

When setting up your first date, be direct about your schedule. Don’t be that person who says something along the lines of, “I think I may have some time this weekend to meet, but I won’t know until the last minute.” What that really means is, “I may be able to fit you in if nothing better comes along.” You can do better.

4. Presenting Themselves Poorly

Gay men are extremely physical beings. If you are approaching a first date all sweaty from a workout, you will not be making the best first impression. Guys have done that to me, and I never wanted to see them again. Wouldn’t you feel the same way if a date did that to you?

Photo of a sloppy man

Tuck in your shirt. Brush your teeth. Comb your hair. It shouldn’t have to be said.

Comb your hair. Brush your teeth. Iron your shirt. Put on deodorant and cologne. Wear something that makes this experience feel special. Wear something that makes you feel confident and sexy. By taking this grooming time, your date will feel an energy that is highly attractive and desirable.

5. Not Giving Undivided Attention

If you are able, be completely unplugged for the duration of your date. Only keep your phone on ring if you are expecting an important call. For example, your mother is in the hospital, and you’re waiting for an update on her status from her doctor.

When I was more actively single, I actually would leave my phone in the car. Not only did this allow me to give all of my attention to my dates, but it also allowed me to wear my fitted jeans more comfortably.

It’s a bad sign when someone can’t take just an hour and a half not to think about work. It’s also a red flag if someone has to constantly reschedule dates “because of work.” Really? They can’t find one hour when they don’t work or talk about work or think about work?

One quality that gay men desire is someone with a really good work and life balance. This is probably ranked one of the top five qualities I hear from dating coaching and matchmaking clients.

If your life is dominated by your work, how are you going to remain focused on dating? The man who sacrificed his time to go on this first date with you deserves the same respect that you expect from him. If you aren’t willing to put work aside for a bit, then maybe you should step back from dating.

6. Not Practicing Classic Chivalry

Being chivalrous is a classic personality trait that never goes out of style, especially in dating. I have always said to my clients, friends, and anyone who will listen that chivalry isn’t dead; people are either lazy or emotionally unintelligent.

Photo of a knight

Open the door for your date, pull out their chair, offer to pay, or practice other classic chivalry skills.

Simply opening someone’s door is such a minor thing, but it makes such a huge difference in dating. It’s also often one of the things people tell me they remember about someone. Or, as another example, if you felt the first date went super well, offer to pay.Practice anything that you would categorize as classic chivalry.

7. Not Practicing Emotional Intelligence Skills

First date conversations should feel equal. Most of us have been on first dates where we were exhausted because we were doing all the conversational work, or we were being talked to without opening our mouths for over an hour.

If you have done your first date homework, you’ll be able to see what you have in common with your date, what you should explain, and what you’ll need to listen to more.

It’s always a good idea to have a strong conversational barometer. We all have first date jitters that can cause us to be in panic mode and do things we don’t normally do. Have you noticed that your date hasn’t said a word during happy hour? Ask him more questions. If you have been the one who’s a little bit more silent, think back to what you noticed in his dating profile and bring up those tokens of conversation.

Dating is All About Trial and Error

Dating can feel like a game, especially on the first few dates. And, to be honest, dating is a game. Games have rules, expectations, and end results. It’s your job to make this process fun. You need to try to find a way you and your date can enjoy playing the game.

What’s good about playing games is that the more you do it, the better you become at it. Keep rolling the dating dice, and I’m sure you’ll find your winner.

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