Is he taking his time or am I wasting mine?

[Anonymous]

This coworker and I have been flirting for many months. It seems to be consistent and slowly but steadily increasing.

We joke and tease each other verbally and physically all of the time. He constantly finds ways to be around me even if that's just coming to my office to blow bubbles "at" me. We are both often caught watching each other and the times we lock eyes, we just kind of silently hold that from across the room a little bit and he'll usually run over with a smile and just ask "what"..

there are tons of "indicators" that he feels the same way I do, but if so why does it seem like it'll never progress? Does he like me?

Possible contributing factors -

age gap (never dated a younger guy, he is much younger than me)

Our families (again age gap, I have kids, I know his mother seems... weary? of our interactions)

We work together, on a management team together, but I'm still his boss (no rules are violated, many coworkers relationships are or have been present)

I'm very open about the fact that I don't date and never really intended to after my divorce (although he does know that at one point my friend stated I liked him - and his flirting increased at that time too)

He has also not dated or been involved with anyone since his last relationship over 2 years ago.

Is this just an endless fun thing for him? Am I wasting my time thinking about anything more than this odd friendship/relationship we have?

[Oliverlogan263]

Dang, that's a tough situation you're in. There's definitely some mutual flirting and chemistry going on between you two, but it's also understandable why he might be hesitant to take things to the next level.

The age gap and the fact that you're his boss could definitely be contributing factors. Even if there aren't any official rules against it, the power dynamic and family dynamics could make him feel uneasy about pursuing something more serious. And if he knows you've been open about not wanting to date after your divorce, that might be making him hold back too.

At the same time, the way he's constantly finding excuses to be around you and the way you two lock eyes seems to indicate he's pretty into you. The fact that he hasn't dated anyone else in over 2 years is also a sign he might be waiting for the right opportunity with you.

My advice would be to try to have an open and honest conversation with him about it. Let him know you've noticed the flirting and the connection between you, and ask him how he feels about it. Make it clear that you're interested in exploring something more, but also understand the complexities involved. See where he's at and if he's willing to take the risk.

If he still seems hesitant, you might have to make the tough call on whether it's worth continuing to wait and see, or if you need to start putting some distance between you two for your own well-being. As much as it sucks, you don't want to waste your time on something that's going nowhere.

Trust your gut on this one, love. You know the situation best. Just don't let yourself get strung along if he's not ready to commit. You deserve someone who's all in. Wishing you the best with this - let me know if you need any other advice!

[ProbablyClueless]

Neither? Lol You said it yourself; you've been very clear that you don't date and never intended to after your divorce. If anything, you'd be the one wasting time because you're the only one who knows that you'd be willing to date him, but you aren't doing anything to communicate that change.

I'm not sure what is supposed to happen here. We're talking about a borderline inappropriate workplace connection that makes other people uncomfortable, where one person has stated a clear boundary that they aren't down to date.

[Asker]

Let me add that he did ask me if I liked him romantically when my friend said that, and I was honest, so he is fully aware that I'm not against exploring something more.

[ProbablyClueless]

Honestly, I would NOT make that assumption at all, if I were you.

If you made a comment like that to me, I would hear that along the lines of "you're fun, but I'm not looking to make any changes." I would not pursue you.

[Babebytheshore85]

@asker he doesn't like you. Let it go. you're too old to be acting like thos grow up

[Anonymous]

Usually women try to date either their age or older because mentally we are ahead of men. Like if you date someone your age you’re already maybe 3 years older, so with this guy it’s like you’re much older all the way around. You’re his boss, you have kids, been married, like you’re so ahead of this guy and too old to feed into mind games. As of now this is just harmless flirting and for all you know that’s as far as he intends to go. But you won’t know for sure unless you ask and if I were you I’d be doing that sooner rather than later.

[Babebytheshore85]

1. He doesn't like you. 2. You're 35 years old acting like a high schooler at work. Grow up, do your job and go home. 3. How are you this old acting like this on the job? He doesn't like you and he sure doesn't respect you. He's just not attracted to you let it go.

[Asker]

didn't know there was an age limit to mutual flirting or wondering about a connection with someone 😅 and I'm 30 sweetheart. I'd rather be youthful and fun than bitter and uptight at only 25 like you ✌️

[Babebytheshore85]

@asker it's work not a play ground you don't mix the two. See this is what happens when you're ugly. Ugly women are known to be desperate and do dumb shit.

[Asker]

Lol yea okay hun. You have a nice day, sounds like you need it 😉✌️

[PeachyPie93]

Well you are saying you don't date, so he probably doesn't want to make the first move. But if he is early 20's I would say leave him alone lol.

[Anonymous]

C'mon, what is the other option here? To work? Who wants to do that. So no. Working would be the real waste of time. This is just killing time.

[In_Trance]

Wasting your time