Why would a guy in his late 30 still be single?

[Anonymous]

There is a guy I like from who who is 39 and he is single. I don’t think he is married or has kids. But have had the feeling he likes me. But is not taking action. (Most likely because of work) i have given him a few hints that im into him but he doesn’t seem to get it. I was thinking either im not being obvious or maybe he is gay? After all he is a really sweet guy. But definitely masculine and not a typical gay guy.

[OlderAndWiser]

1. Some guys don't settle down until their late 30's. He may have been in a relationship that ended traumatically and be scared of getting involved again. Maybe he simply doesn't see an advantage iin being in a committed relationship. The only way to learn the answer is to spend time and get to know him. That's what dating is all about.

2. He is a co-worker or a supervisor?

3. Maybe he has noted your efforts and is not interested.

4. Girls always want to give hints and then complain that guys don't take your hints. MAYBE you should try being more direct.

5. Do you work with people who might occasionally go out to a happy hour after work? Organize an outing and invite him as part of the group, then spend some time talking to him in this group setting. Far less pressure.

[Asker]

@olderandwiser he is a supervisor but not my supervisor. I moved to his department in November and didn’t know him until then. He seemed to be attracted to me and was friendly with me. We interacted online and only met him for the first time in person two weeks ago. He was watching me a few times and really nice. The next day I sent him a message and asked about a concert he went to but didn’t reply. Today I saw him and he completely ignored me.

[OlderAndWiser]

He may be reluctant to proceed because he is a supervisor and your company may have very strict prohibtions against him socializing with you.

[Asker]

My company doesn’t

[OlderAndWiser]

How do you know that?

[Asker]

@olderandwiser because a few other people have dated and also supervisor dated other staff.

[OlderAndWiser]

They may still have a policy but enforcement is lax. And he may be afraid of being the guy who gets t enforced against him. Maybe not, but it's a possibility. And maybe he is just worried about people gossiping at work.

[Asker]

@olderandwiser he probably realised I like him and it worried him. Hate that at work awkwardness. Happy to be friends. How can I get him relaxed about me again?

[OlderAndWiser]

Organize a happy hour event and talk to him but spend more time talking to other guys. That sends the message that you are not focusing your attention on him. Or engage him in conversation at work and mention a new guy that you have started dating; that is something that you likely wouldn't do if you wanted to pursue him.

[serious]

Okay so why does that surprise you so much?

I am 35 years old and I have always been single. I wish to be single for life. I never even had any proper friendship in my life. For me yes I have my reasons behind my decision

In the same way men who have been single or who are single of course will have their reasons behind their decision and that is not surprise at all. It is also a fact that no matter how good a person maybe, they may even be one of the best people out there but still not everyone is meant for love and relationships. Yes everyone deserves love but not everyone will get that. It is true.

[milkov]

You might have to spend time with him more to observe his behavior. Being gay is not just being "gay gay", I've seen a lot of masculine man who are heterosexual. So let's not jump into conclusions about his sexuality.

Anyways, you need to ask him why he's still single and you may be able to find out that he wasn't over her ex or something or maybe he's just too cowardly to ask a girl out.. or worse, he's waiting for someone.

There are a lot of possiblities to point out. The only way to know is to ask and observe.

[midnightcavern01]

Chances are he's divorced or had troubling relationships so unless you're up front about it, he probably won't acknowledge you

[abc3643]

I doubt he is gay.

I was that guy, basically, although I did get married at 38.
Don't give hints; be active in talking to him about the possibility of going out; it's not hard.

In fact, use the damsel-in-distress method...

This means fabricating some "problem" in which you need advice or his assistance.
If he is a straight male, he will respond and help you. Consider offering to "pay him" for his help by making him dinner or taking him out to dinner. This becomes a de facto date and you can take things from there.

[EA1988]

You said "But is not taking action. (Most likely because of work)" do you work together? If so that's most likely why. Me myself I've skipped on potential romantic opportunities because of this particular situation. Even if I like a girl i work with and she seems interested i usually will not push it, unless I'm sure there is a real possibility of something serious. It is just not worth the off chance, as a man in the work place to misconstrued the situation. There is too much at risk as a man particularly if you are in a professional environment.

[MrCommodore]

It can easily happen if his last relationship broke down in his late 30's. He probably is just afraid to misread your signs, as in a work environment a wrong move can have lasting consequences, so he may tell himself that you are just being friendly.

[Nivinxus]

How would we know? There are at least 4 billion dudes on this planet, a sizeable portion that is single. Understand they can be single for any reason, doesn't exactly have to be logical. For example, he might be recovering from a bad relationship, maybe he is on some sort of spiritual journey, maybe he is an asexual guy. Whatever the reason, you won't know by asking us, our guess is as good as yours.

[Harryortho]

You need to be direct at some point and be ready to hear something you like or not like I think. Let him know you like him directly and want to be more serious with him, to see how it is to date each other and maybe become boyfriend girlfriend. He might say he isn't ready or other things or he might say he likes you too. I guess you need to be ready for that risk.

[BeMuse]

Ah he won't give you the time of day so it's not you it's him... He must be gay because obviously you're the center of the fucking universe. Fucking lame.

[Anonymous]

Some guys are single their whole lives. They just prefer it that way.
That doesn't mean they're not having sex though. A lot of them have on and off girlfriends or even hire a hooker (which is way more common than you'd think)

[TrillXHippy]

Are single women in their late 30s lesbian? 😐

[FunkyMonkee]

HE CAN'T FIND A BROAD!!

[Anonymous]

I am autistic.