I (34F) have been working with James (40M) for the past year. I always thought he was cute, but that was the end of it. I’m easily able to appreciate a good-looking guy without developing feelings etc. Never thought much about him beyond that and work related things. Here and there things were a little flirty, but nothing consistent.

My whole life I’ve been responsible and professional. I work in a very male-dominated field and lots of women (often unfairly) earn themselves a reputation just for dating or hooking up.

My career is the most important thing to me, so I’ve always been very careful never to even flirt or make any suggestive comments. As such I am largely seen as an equal and am well-respected with a pretty promising future.

Anyway, about two weeks ago we were involved in a work project and things got a little flirty. It spread over to text and for the past two weeks it’s been getting increasingly flirty. I’m going to be honest, it’s been so much fun. It was nice to feel attractive and wanted. There’s nothing more there than flirty fun, I don’t think either of us has any kind of thoughts of serious dating, but it’s definitely building up to a hookup. It’s been a long time since I’ve ever felt like anyone wanted me or looked at me that way. If I’m being honest it’s just been a fun boost to my self esteem. I’ve never been courted this way before and it’s been awesome.

I know for the sake of my career I should put an end everything, and in fairness shouldn’t lead him on. But I’m so tired of being the responsible and professional one. I’m 34 years only and I’ve only ever had serious relationships, and I just want to have fun. He’s fun. There’s no pressure, there’s no attachment, we’re both adults, we’re both attracted to each other, there’s lots of chemistry, and we’re both having fun.

What do I do? Do I put my reputation on the line for a fling? Do I allow myself to have some fun and take the risk that no one finds out? Or do I just stay the same old cautious me and end everything?

TL;DR My career is super important to me (34F). Things have gotten flirty with a coworker (40M) and I’m dying to have a fling with him. But should I take the risk to my career?

EDIT:
Well the consensus is pretty clear that I should end it all immediately. This by far isn’t the first time I’ve been hit on at work, and it won’t be the last. It IS the first time that I’ve ever felt like following through with it though. I think I knew the answer before posting, but just needed the reminder. It’s frustrating to always be responsible and I’ve been that way my whole life. But you’re all right, it’s not worth the risk.

Maybe like someone posted I am having a midlife crisis and he was just in the right place at the right time.

Several people also suggested I get hobbies or meet people outside work. I have several hobbies, but like I said in my comment, that’s not really a priority for me right now. I’m not too long out of a very long term relationship and I’m happy on my own. This was unexpected fun and an ego boost, but I’ll just hold onto the memories of that fun and cut things off when I’m back at work tomorrow

Thanks everyone

33 comments
  1. Generally, it’s not a good idea because of the complications if you break up, especially if it’s with a supervisor.

    But many, many people have met their future spouses at work. That’s where you meet most of the people in your life. If it works – happy for you.

  2. Honestly if you trust him and can have an honest conversation where what happens outside of work stays outside, everything remains professional no matter who’s feelings end up getting hurt – and you just want to hook up on occasion no strings attached…go for it. But ONLY if you TRULY think both of you are emotionally mature and trustworthy enough to handle a situation like that.

  3. Think about how awkward it would be to work there if you ended up hated him for some reason. If you can deal with that, then go for it. Plan for the best but expect the worst, just in case.

  4. Protect your career – fling/date/hookup with men who do not work in your office/company.

  5. Don’t shit where you eat. If your career is that important to you why do you even want to risk it?

  6. Nope … far too much risk, for an unknown (but probably not worth it) reward.

    Join a group activity (dancing, art club, dining group, etc.).

    Get out and socialize, it’s a big world out there!

  7. Speaking as a man that has ruined a few careers in my life because I yielded to temptation with coworkers I can tell you that the most fun I ever had in my life was in those flings but looking back it cost me a ton of money and a few ruined careers.

    DANGER!!! Run, don’t walk away from that fling. You’re suffering a midlife crisis and about to endanger and likely even ruin your career and I can guarantee you that your fling WILL be outed and it will at least damage if not destroy your career!!!

  8. I personally have found in these situation that anticipation (ie the flirting etc) is two thirds of the pleasure. The reality is fun, sure, but if you feel like it is just going to be a fling and nothing more, is it really worth it?

  9. What you’re feeling is totally legit and you deserve to have some fun. There are so many other places to find that well deserved fun though! Your career is not worth it, and usually it’s those “fun” times and can end up leading to huge regret if you mix your personal with your professional. Your gut feeling about it is not wrong!

  10. First real job after college and was interested in a woman in a lower level role. Not affecting my work and next thing the CEO was lecturing me about not messing on your own doorstep. Ironically he had two assistants one to do the work and one to look good

    Fast forward and had to leave best job I ever had over involvement with woman at work.

    Don’t do it. But I see you’ve already taken this on board

  11. I’ve done it before. It resulted in a marriage and we had to work under two different buildings. Today? I wouldn’t do it. I’ve seen the good, the bad and ugly when it comes to work relationships. You might be quiet about it But dudes talk just as much as females do.

  12. Have you tried Tinder or any dating apps? Tinder is that just hookups, I found my fiance there. Plus is just fun to flirt and chat with people. It’s definitely good for an ego boost and it’s not in a way that would affect your job.

  13. I guess I have terrible advice haha. I was going to tell you to have some fun with him.

    The way I see it, you constantly resist these urges but this one is different. Much stronger. Maybe your gut is telling you there might be something there. This guy really makes you feel good when you flirt with him. Thats a good sign in my opinion but yea. Professionalism and stuff…

  14. Unless you’re absolutely dying to do him, don’t. Not worth it.

    Be irresponsible and fun outside of work, meet strangers irl/on dating apps, get courted, highlight you’re seeking being courted in interested ways/sapiosexuality. There’s an ocean of men who can fill this gap/need for you, who aren’t your coworker, you got this!

  15. don’t pursue it, you guys are coworkers and something always happens. i hooked up with a couple of coworkers before and it just makes things incredibly awkward and uncomfortable and people can feel that tension/uncomfortable feeling. so no matter how well you play it off, people will know something happened. i wouldn’t pursue it.

  16. I’d go with the flow girly. Dont over think it. If you think you should stop, stop. If you think you’d like to see where it goes do it!

  17. Usually work places have a policy on work relationships. Whether it is as simple as you can not date a direct report or someone whose job you could impact to as complex as many different levels and having to disclose the relationship to HR. Bottom line, it usually isn’t worth it and inevitably someone gets hurt and leaves the company. If you value your career, there are plenty of ways to find companionship without jeopardizing your career.

  18. You are in a field that is male dominated and has an existing reputation where women are viewed as hooking up with coworkers.

    Be one of the Bros not one of the stereotypes.

    Yall can be flirty, but both yall are risking each other’s jobs and everyone else is going to have to attend one of those “dating at work” seminars if things go sideways.

  19. Be careful. I had a work fling once with someone. Neither of us wanted anything serious out of it. We just had great chemistry and wanted to have fun with each other, so we decided to be FWB until we got tired of it. Long story short, we fell in love and now we’re getting married. Happiest accident of my life.

  20. No way, the risks far outweigh the benefits… there’s no shortage of men who’ll give you a fun flirty hookup and just disappear into the void

  21. I would do it. You only live once and who knows where it might lead. Don’t stay the same old cautious — you’ll end up regretting doing so when in 20 years and will probably be wish you did it. Have some fun and if it ends up being a mistake, you weren’t the first and definitely won’t be the last to make it.

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