My brother met his boss through his girlfriend at the time. He was working for him and dating her for about 7 years. they had a BAD breakup, BAD BAD Breakup.

anyway my brother is now co-owner in the company and the relationship with the father couldn't be better. Oh and he's now married to someone else and sees his ex every once in a while at company/family meetings.

So it can work, it just depends on how honest you are with the father. Her father pretty much knew what was going on almost the entire time.

 

Yeah for all you know she might think your gay and she's looking for someone to go shopping with.

 

I would talk to your boss about wanting to take her out first. If he gives you the okay, then ask her out. Its the only way to keep trust with him.

 

Look at your gross earnings on your last year's W-2 and ask yourself if you have ever had any ass that was worth that. 'Cause that's what you are going to lose when it goes bad.

 

This man speaks the truth.

 

 

It's a gamble either way you look at it. From the sounds of it your boss is a pretty straight forward guy, and I would hope he could keep the professional separate from the personal. If she didn't say anything, then Id lean towards just keeping it cool and not dating or pursuing her.

However, she has confronted you, which takes a little weight off your shoulders. Like someone else said, you never know, your boss might have wanted that to happen and maybe was trying to set you two up. He obviously knows you well, and trusts you. In many ways, he'd probably rather have you date his daughter then some random dude she brings in.

I think telling her you are dating someone else is a mistake. What if your boss finds out you lied? Then what judge of character would he have of you? Think about your boss and how he has reacted to things in the past etc. If you feel comfortable with who he is as an individual, then I wouldn't worry to much about it, unless your REALLLLLLLY **** up.


Overall, I think there are way too many pessimists in this thread. I say proceed with caution...

 

epic win if you ask me

 

I wouldn't get publicly involved with my boss's daughter. I would however, take her to KFC and poke her in the car twice a week. No one has to know.

 

Go for it, I know a few couples that met at work and being the boss' daughter can be a good thing. I say go for it.

You seem to be pretty genuine that you even stopped to think about this rather than just going for it. Treat her as a gentleman would and take things slow, opportunities like this don't come up every day. And do keep your boss in the loop if you are going out, no sneaking behind his back!