Going out with female boss...advice?

[Colopez]

I had a crush on my female boss for a while and I believe she was aware. She eventually suggested we meet outside the workplace and we've been out twice, but nothing has happened yet. We haven't hooked up or talked about any interest for each other. We've had a good time, but I haven't really made a move because I was concerned with the whole boss thing...even though I'm only at the office about two or three times per week and hardly interact with her.

Some time has passed since we last went out and she said she would like to meet up again. I feel that if I ask her out I need to make a move. While I still think twice about mixing business with pleasure, I also believe in taking risks and not being left with doubts. We've never discussed anything about us dating or hooking up, but it was quite obvious that she was interested in some way.

What are your thoughts on this? How should I approach her next time?

 

[thorwynn]

Ask/invite her to go out while she's interested, don't keep the dating part too long. I think (based on my experience) she already wants action from you and you just need to take a little risk. Just don't try to act or show some desperation

 

[Tomo]

1) BIG No.1!!!! - Are you willing to suffer the repercussions? Have you ever heard the saying and numerous posts here about not sh*tting where you eat? If you are prepared for the fallout if things go sour then kudos
2) Unless you two have set the boundaries, know each others intentions i.e. FBies, take it SLOW. Don't move too fast - don't build a castle without its foundations.
3) Prepare for workplace glossip.

Now to answer your question, just treat her like any other girl you are keen on. Conversate normally and slip into the conversation when relevant, flirtations and asking her out. You two have already gone out a few times now so for the next date simply escalate your touching and flirtation to gauge her interest. If she responds then kiss close.

 

[gravityeyelids]

are you planning on still being at this job and working for her a few more years down the road? If so, don't go after her.

But if you decide to... find an area where there aren't people nearby..slam her against the wall, grab the back of her head, and gently (well..not too gently) pull her hair down and shove your tongue down her throat.

If she's the one that suggests that you meet outside of work, she's probably into you...do you guys flirt and stuff when you go out?

 

[Cremasta]

Is she planning on leaving her job? It sounds like she might.
Any boss halfway competent will know that you don't date one of your subordinates, it's just looking for trouble. She may be able to keep everything on the level at work, but the perception from other workmates can cause dramas.

If she's planning on leaving, then full steam ahead.
If she isn't then tread carefully my man, you're playing russian roulette!

 

[TheGambino]

Suck her titties

 

[VladPatton]

Huge mistake. This is not a risk, this is a 'regret maker'. She's gonna be your boss in the relationship as well, and when you don't comply, things will get real messy real fast. Abort mission.

 

[Dgwizdal]

Huge mistake. This is not a risk, this is a 'regret maker'. She's gonna be your boss in the relationship as well, and when you don't comply, things will get real messy real fast. Abort mission.

This.

 

[Johnny Alias]

I'm your bud on this one... I did date my boss!

It was a long time ago but we went out for like 3 months. It was fun! She made the first move on me and it was a good laugh. Don't let anyone talk you out of it! Contrary to what everyone thinks... YOU HAVE THE POWER! That's right! You do!

Superiors aren't supposed to go out with people below them. It's very frowned upon and is considered an abuse of power... but you're not the superior! SHE IS! She's the one breaking the rules. If push came to shove you can say she bullied you into it!!!! Therefore you can ride this out and have a laugh. Even if you two break up she'll be wicked paranoid you'll tell people and she'll be putty in your hands...

Trust me. This happened to me. I couldn't even knock on her office door without mine getting all frantic after we split. GO FOR IT!

 

[TheCWord]

Huge mistake. This is not a risk, this is a 'regret maker'. She's gonna be your boss in the relationship as well, and when you don't comply, things will get real messy real fast. Abort mission.

Yes, almost a 100% chance of regret.

However, I once started going out with a girl who was my superior but I absolutely crushed her with my frame in the relationship. It was always fun to be at the office where, officially, this girl was above me... then we'd get home and she'd be on her knees.

...Go for it, OP! hahaha.

 

[GS750]

Are you effing kidding me? Dating your boss? Holy sh*t. This will get ugly.

 

[Eph]

...Do you really want to date someone, of a gender driven by their emotions, who could fire you if anything went wrong? This is why they say, "don't sh!t where you eat". If you think she's interested, tell her nothing can ever happen between you two. Driven by emotions + power = irrational decisions.

I'm your bud on this one... I did date my boss!

It was a long time ago but we went out for like 3 months. It was fun! She made the first move on me and it was a good laugh. Don't let anyone talk you out of it! Contrary to what everyone thinks... YOU HAVE THE POWER! That's right! You do!

Superiors aren't supposed to go out with people below them. It's very frowned upon and is considered an abuse of power... but you're not the superior! SHE IS! She's the one breaking the rules. If push came to shove you can say she bullied you into it!!!! Therefore you can ride this out and have a laugh. Even if you two break up she'll be wicked paranoid you'll tell people and she'll be putty in your hands...

Trust me. This happened to me. I couldn't even knock on her office door without mine getting all frantic after we split. GO FOR IT!

As for the above, if you honestly believe anyone's going to take your side if you get fired, then you're living in a fantasy world. Its way too easy for women of any position to play victim.

 

[Jaylan]

Career > Women

Don't do it OP. Id tell a woman the same thing--Career > Men. Money is how we take care of ourselves. We all need it.

Your job is your livelihood. And you could fvk yourself for years to come if things go bad.

 

[DragonBlood]

Just go for it Colopez. Most of the people in my office are dating someone else from the office or close friends of. The only problem I see here is you are over thinking it.

 

[Jaylan]

Just go for it Colopez. Most of the people in my office are dating someone else from the office or close friends of. The only problem I see here is you are over thinking it.

Dating someone in the office is A LOT different from dating your boss. Sure id chance dating a coworker. But dating a superior and having great potential of sabotaging my source of income? Nah.

 

[Johnny Alias]

...Do you really want to date someone, of a gender driven by their emotions, who could fire you if anything went wrong? This is why they say, "don't sh!t where you eat". If you think she's interested, tell her nothing can ever happen between you two. Driven by emotions + power = irrational decisions.


As for the above, if you honestly believe anyone's going to take your side if you get fired, then you're living in a fantasy world. Its way too easy for women of any position to play victim.

She can't fire you dude. You could sue the company for sexual harassment and what's more she knows it! She's the SUPERIOR and should know better! That's the point! But whatever. AFC it. Hell, me and that old gal are still friends on FB.

 

[VikingKing]

Your going to have a bad time.

https://www.youtube.com/watch?v=ynxPshq8ERo

 

[Eph]

She can't fire you dude. You could sue the company for sexual harassment and what's more she knows it! She's the SUPERIOR and should know better! That's the point! But whatever. AFC it. Hell, me and that old gal are still friends on FB.

I don't know where you live, but at least here in the US, the chances of a male succeeding in suing a female for sexual harassment are slim. Besides, a woman who just got dumped or heartbroken would fire her ex in a heartbeat to "get even" with him. Superior or not, the fact of the matter is she's a female who's seen as innocent and "can do no evil", while the OP is a male. This is bound to be trouble for him.

 

[Johnny Alias]

Well I have to disagree there. I do live in the US. As long as he has incontrovertible evidence that they were dating he'd be gold. E-mails, pics, whatever. This is her abusing her power in the case that a termination occurs. Pure and simple.

And for the record a friend of mine name of Mark once got a superior fired for sexual harassment. It's simply not that difficult. She would corner him in file rooms, leave panties in his backpack, etc. She got the sack while he got a nice check.

OP its up to you. Its not often that I'm the dissenting opinion but based on my experience it was a definite win. I don't know many other dudes who can say they fvcked their boss.

 

[skinnyguy]

My advice?

Put it in her butt.