[Simplex3]

Originally Posted by trndobrd

You are already dating the boss's daughter, what you are really wanting to know is if you should tell the boss. I'm guessing that he is OK with you spending time with his daughter since he paid for you to take a week long trip to Mexico and share a hotel room with her. It almost seem like he set you up.

Tell the boss. Here are a couple ideas on how to present the idea:

1)"Bob, something I wanted to ask you about. Sally and I had a great time hanging out in Mexico. I know it's a little awkward, but I would like to ask her out."

2)"Bob, it seems a little strange telling you but your daughter is a a freak. I was hitting it in Mexico and I would like to keep nailing her, if that's OK with you."

3)"Bob, your daughter is pregnant and I think I know who the father is."

Glad I could help.

I'd probably go with #1.