Guys Reveal The Struggles Of Flirting With A Cute Guy You Are Not Sure Is Gay

A gay man posed a simple question on Reddit this weekend, asking if “anyone had a story about introducing yourself to a guy who you were not sure was gay?”

khubbar2 writes:

Today I was sitting in a coffee shop and saw this guy I have seen a few times. He is insanely handsome and sat on a couch with poetry and looked as if he was writing himself. SO, I decided to move my stuff and sit next to him on the couch. I asked him if anyone was sitting there and he smiled and said no. So being 100% distracted, I decided after an hour or so that I am going to use the bathroom and ask him to watch my stuff. When I did, he smiled and said sure. After returning, I said thanks and that I was sorry if I interrupted his writing (he was balls deep it seemed like). But he didn’t spark up a convo and I didn’t gain the courage to either. I’m pretty pissed at myself for being a pansy but idk I have yet to go up to a guy that I wasn’t 100% sure was gay.

Thoughts? Stories? Rants?

A Redditor began by offering khubbar2 this piece of advice:

“Do you mind if I ask what you’re writing?”

If the guy’s doing any kind of creative writing, he’d probably enjoy telling someone about it, whether it’s his “novel” he’s been working on or he’s a journalist or whatever.

Let’s get down to brass tacks, though. If the guy’s writing in a coffee shop, it’s likely something he does a lot. All you have to do is go back to the same place occasionally and keep an eye out.

If you see him again, that itself is your in. Say anything (comment on the weather, sip your coffee when it’s way too hot and go “Ow fuck!…oh my God, excuse me”, whatever) and then “Oh hi, I think I’ve seen you in here before. I’m ____ btw”

Jake shared his story:

I was at a party, and I had started chatting up a cute guy. Not really getting my hopes up or anything, but the conversation was interesting. He mentions if I think any of the girls at the party are hot, to which I’m just like “honestly, I’ve been eying the men mostly”. After a while he’s like “well I actually am eying both” and that’s how I met a new friend who I sometimes bang…

Another redditor shared his experience:

I have a pretty similar story. A few years ago I was studying abroad in London. One morning, I was waiting on the platform for the tube (London’s subway) and I noticed this really cute guy also waiting. We smiled at each other, and kept catching each other’s eyes as we got on the train. I kept thinking that I should say something to him, but before I could think of anything to say, he got off.
I was kicking myself for not saying anything to him. So I, like yourself, vowed that the next time I saw him, I would say something. But I was sure I would never see him again, cause what are the odds of seeing the same person on a subway platform two days in a row? New trains come every 2-3 minutes, so theres a really fast turnaround.

So the next day comes around, and sure enough, I see him again. We do the whole smiling at each other thing again, and then get on the train. I kept thinking back to what happened the day before, and how I hated the feeling of not saying anything. So I figured the feeling of potential rejection would be better than the feeling of regret over missing my chance. So I walked up to him and said hi. We ended up hitting it off and exchanging numbers before he got off at his stop, and then hung out a few times after that.

I think it helped that I was only studying abroad there, so it was easier to put myself out there. But knowing how crappy it felt to regret not saying anything is what really pushed me to say something. I think you should definitely just strike up a conversation with him. Even if he isn’t gay, it’s still a good way to make friends.


User deebo2008 writes:

A few weeks back a cute guy sat next to me on an airplane. About midway through the flight, I finally worked up the courage to talk to him and it went great. We talked for the rest of the flight and then after we landed all the way to ground transportation where we had to part ways. All I got from him was his name and I’m still only about 80% sure he was gay. I never asked for his number, but I wish I had. Either way, I’m really glad I talked to him!

jpfleong details his struggle:

I’ve been constantly making eye contact with this guy on these weekend classes, and really wanted to ask him if he’s interested in grabbing coffee. I’ve said “hey, how are you?” three times already, and that was as far as I got.
Last class next week, and I’d totally regret it if I chicken out again!

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sdsinger80 shared his story:

Right about the time I realized I was ready to start an actual dating relationship, I also joined a community choir. The choir was mostly seniors who needed a social activity. They were all older, grandparent types. The choir director was about my age though; He was quirky, passionate, and very focused. I found him funny and interesting—but just because he liked music didn’t exactly made him gay right? But you know, my gaydar did seem to “ping” so…why not?

I waited until after our concert season was over. I figured that if he said “No thanks” to a date with me, I didn’t want things to be awkward in rehearsals. I sent him an email after our last concert, and just said something like “Hey, I only know how to be direct, and I don’t know if you are interested in guys or not, but I was wondering if you would like to go out to dinner with me sometime?”
He emailed me back, and seemed appreciate that I was direct and asked him out. But then he stated “Actually I just started dating someone, and things are going really well with her.”

WITH HER!

Ooops. Good thing I waited until after the season was over. I didn’t go back to choir. HA!


LaughKookaburra writes:

So, I’m at this holiday party thrown by some friends from church. This particular church had a pretty heavy gay contingency. And a visiting pastor from another church was in attendance. He was friends with a lot of the guys. We started chatting and all the signs were there, great conversation, that tingly new crush feeling. In my head I’m 20 miles down our future path wondering how I’ve adapted to being a pastor’s wife. I ask him out to dinner. He accepts. I’m skipping home in a tacky sweater with a reindeer on it.
Fast forward to our date. I pick him up. We’re in the middle of our meal when it “comes out” that he’s straight and that I thought we were on a date.

We had a good laugh about it. And remained friends. You know, my gaydar still questioned him. And all my friends gave me the “No fucking way!” when I told them. But he was such a genuinely good guy that I didn’t care and was just happy to have him as a friend.
TL/dr: introduced, asked out, and quasi-dated. No regrets. Ended up with a good friend.

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Cendruex writes about his struggle:

I’ve been trying to work up the courage to ask out the guy in one of my classes for a while now, and I’ve just been trying to figure out if he’s gay or not. He’s really quiet unless you talk to him and is mostly absorbed in a book or his notes, so we don’t make eye contact or anything like that a lot. But he’s caught me looking at him a few times (the professor stands off to the side, so I can get away with checking him out for half the class period if I wanted). He’s always bright and smiling whenever I ask him anything, but we haven’t talked that much. We have an exam on Tuesday, but I told myself I’m going to ask him out to lunch on Thursday, now or never!

Do you have a similar story? Share them in the comments section below.

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