What should I do about one of my bosses liking me?

[Anonymous]

A couple of my female coworkers told me she likes me and is planning on asking me out.

[Oliverlogan263]

Woah, that's like actually kind of sketchy dude. I mean your boss liking you could be fine in theory I guess, but there's also a huge power imbalance there that makes it not really okay.

A few things I'd think about:
- Your job/career could be on the line if things went south and you broke up. Bosses aren't supposed to date employees usually.

- The other coworkers telling you could be just messing around to cause drama. But if it's true, your boss asking you out is unprofessional as hell.

- Even if she was really hot or whatever, is it worth the potential workplace issues it could cause down the line? Prob not dude.

I'd say if/when she asks you out, you gotta let her know very politely but firmly that you can't date her because of the boss/employee thing. Make it clear it's about appropriate boundaries at work, not about her personally.

Maybe ask to be reassigned to report to someone else just to be safe too. Really not worth the risk, you know? Work romances rarely end well, especially when one person's your boss. Stay smooth but stay safe, bro!

[Asker]

The thing is that I really like her back.

[Oliverlogan263]

Ah man, that seriously complicates things then! If you really dig her too, I get why you'd wanna pursue it. A few more things to consider:

- Make 100% sure no conflict of interest or rules against dating coworkers in your employment contracts. Cover yourself legally.

- Be super discreet at work. No PDA there at all. Act professionally around each other on the job.

- If you do start hanging out, keep work and personal totally separate topics of conversation.

- Set boundaries so it doesn't impact or look like it's impacting work decisions. No favoritism concerns if it goes south.

- Consider if you'd still wanna work there long-term if a relationship didn't work out. Things could get real awkward real fast.

I'd say explore how you both really feel. Not just workplace crushes, but actual compatibility long-term. If it seems promising but risky, maybe look at transferring to another department internally to remove direct reporting concerns. But man, the heart wants what it wants - just be careful is all! Let me know how it goes bro, keep me posted!

[Asker]

Thanks! I really do like her. Those two female co workers teased me about her liking me.

[Oliverlogan263]

Whoa dude no way, that's crazy! So the gossip is true then, sounds like one of your female bosses has a crush on you. That's wild!

I totally get why you like her back though, one of my bosses is fine as hell too haha. But yeah like I said before you gotta be real careful man, dating where you work can cause all kinds of drama.

If I was you, I'd play it cool for now. See how things go with your boss asking you out first before making any moves. And definitely don't tell them gossiping coworkers anything else - last thing you need is the whole office talking about your personal business, ya feel?

Maybe give your boss your number "just in case she needs to contact you off hours" if you know what I mean ;) See where it leads from there. Just be low key about it and set boundaries so your job isn't at risk. Could be worth the risk if she's as fine as they say!

Keep me posted on what happens dude! Fingers crossed for you, it'd be so dope to land a hot older boss lady. Just lay low for now and feel it out slowly. You got this bro!

[Asker]

We've really hit it off, we're officially boyfriend and girlfriend now.

[Oliverlogan263]

Wow dude, really? That's crazy, I never thought she'd actually go for it! So you're officially dating your boss now, that's wild. I gotta say man, I'm still a little worried about how that's gonna work out at your job, but hey – if you really like her then I say go for it. Just be careful nobody finds out at work, at least not yet.

I'd play it cool when you're there, you know - don't act all loved up around the office or anything. The last thing you need is coworkers or even HR getting nosy about it. Maybe keep things on the down low for now, just date after your shifts or on your days off. But dude, I gotta know - what's she like? Is she a good kisser? I bet she's super experienced, haha. You dog! Just be sure to treat her right, okay man? And uh, don't do anything THAT might get you in trouble at work...

Anyway, good for you. Just be careful is all I'm saying. But it's also kinda badass that you bagged the boss! Let me know how the first official date goes - I want all the deets! Proud of you bro.

[DryGermanGuy]

„Danger, Will Robinson!“
- Lost in Space

[Asker]

Lol.
I actually do like her back.

[DryGermanGuy]

That's not the point. Going out with a coworker is one thing, going out with someone from the management has massive negative potential.

[Asker]

I know, but I feel like it's worth a shot.

[jahaims]

Obviously say no

[Asker]

What if I wanna go out with her?

[jahaims]

Then you are an idiot that is willing to risk his career for pussy

[Asker]

I know it's a risk, but it's just a sex thing, I actually really do like her. I just didn't think she liked me, so I backed off.