Should I explore a relationship with an older female coworker?

[purplewingsofdesire]

I'm 26 and she's 38 years old. Dating and relationships with coworkers are allowed at my workplace.

We first caught each other's eye at an event before she was married and have stared at each other over the past five years. She accidentally revealed she was separated because she swore and said I wasn't supposed to know.

When we go to lunch with other coworkers, they melt away, she’s always asking if I want to go to conferences with her, so it’s just us, and we look at each other after laughing in a group setting. I went on vacation and when I got back she said she missed me. Said she needed someone funny and edgy. Also, I was sick with a cold and she said my right eye was a little irritated but I looked good.

We talked about meeting up for Halloween but she had something going on. She got me to help on her side project. She told her boss that I was helping her. And her boss said they hoped we would have fun together.

Met in the parking lot and saw each other from afar and our faces lit up. She was unusually wearing perfume. We proceeded to laugh about inside jokes from coffee teeth staining to her apprehension about kimchi. Bantering for five hours and jokingly calling out each other's flaws We were working on something very close together and I mentioned the consistency being like creme brulee and she agreed, and we just looked so deeply into each other's eyes. I thought we might touch hands.

In the office two days later, at the office, she recently said we’re both controlling and perfectionists. I said I’m glad we haven’t butted heads. And she said that would happen elsewhere and then threw her head back and messed with her hair... then started laughing a lot and said she was just playing. A little later she knocked over some markers and I helped pick them up and we turned and just stared into each other's eyes.

Updates

8 mo

Interestingly, I was trying to gauge her reaction, so I mentioned other women who I was dating or getting set up with, and she said that she was surprised I was into women. I think maybe her comment was solely a test or something because we already seemed interested in each other.

Updates

8 mo

This is extreme, but in the office, I was talking about the difference between a forward slash / and a vertical pipe|, and she mimicked with her hand. I got up to show her computer and she asked if I’d t*ar her a new one if she used the wrong one.

Updates

7 mo

Yesterday we found out we liked the same color. We made eye contact, and she seemed surprised. She jumped up to go to the door and left her laptop behind. Not sure why the strong reaction. Under her breath, she said that she would have to change her yellow-blonde hair color since, I like yellow. As if it's somehow a problem. She also said I'm funny, but sometimes she wants to flip me off with multiple hands.

[Amy_Mi]

There’s undeniable chemistry, the kind that hums in the silence between laughter and eye contact.

But before you let the spark pull you in, recognize what’s at stake.

She’s 38, recently separated, and you’ve built a rhythm inside a professional environment.

That means blurred lines, emotional vulnerability, and potential fallout if the dynamic shifts.

Attraction doesn’t automatically mean alignment, sometimes it’s curiosity wrapped in timing and tension.

Ask yourself three things,

Would this connection still feel magnetic outside the workplace?

Is she emotionally available, or just seeking comfort after separation?

Can you both handle the professional consequences if it goes south?

If your answers are grounded not just driven by adrenaline then proceed with honesty, boundaries, and clarity.

But if it’s built on “what ifs” and stolen glances, maybe what you’re feeling isn’t love yet it’s temptation testing your discipline.

Be the man who thinks beyond the moment.

That’s where true power lies.

[SueShe]

Dating and relationships may be allowed at your work. I don't think that any company specifically prohibits them.

Even though they are allowed, that is not a good idea. Dating co-workers is only a source of problems. There will be jealousy and favoritism and that is going to make the work environment more difficult.

Also, she is separated and not divorced. Fornicating with her would be the perfect excuse for her losing a divorce court case.

Another serious issue I see here is that both of you are controlling. How do you think that will work if one has to give in. That is a recipe for a disaster.

Keep this relationship on a professional level only. Too many things can and will go wrong otherwise.

[Anonymous]

Maybe you should try, if you're really into older women, at least she is not 40 or older.

[Opinion Owner]

Thanks for MHO

[Unap0logetic_]

I’ve seen it people having sexual relationships with their coworkers, I feel that some people are able to do this without causing drama but not all people. I would be very careful if I engage in this kind of thing because some people don’t have your best interests at heart.

[butterly248]

U know what go for it

[purplewingsofdesire]

She seems pretty overt, which is cool, but also a little shocking

[Abbycado]

Nope

[purplewingsofdesire]

Thank you for the advice. I'll reconsider

[In_Trance]

Don't fuck your coworkers