I am in love with my boss! Now what?

When I broke up with my ex three years ago I thought I would never feel this way about another woman. Fast-forward to now: My current boss at work is about two years younger than I am, I think we have amazing chemistry and she is very cute.

I've worked with her for almost a year, when we first met I thought she was a dweeb, but then I began to admire her, and then I began to think she is beautiful although she is not the sort of person I'm typically attracted to. We don't have much time at work to talk but I always feel like we have a lot in common and would have fun if we could spend time together. I feel this way about very few people so I feel I can't waste this opportunity, how can I ask her out? What can I do to improve the chances that she'll say yes? I hope she will at least give me a chance.

I was going to talk to her before she leaves work and hand her a piece of paper that says:
Hi Her Name, Although I usually prefer to keep my work and private life separate, I think you're really interesting and want to know if you will go out with me this weekend.
I promise not to talk about it at work, and if you say no I won't mention it again and it won't be a problem but I had to ask because I think we would be fun together.
I'll put a box for yes and a box for no; what do u guys think?


Most Helpful Girl

  • My job forbids inter office dating. If something like that were to happen we are to talk to our supervisors and someone well be let go or transferred.

    It makes sense businesses don't want the drama or favoritism at work.

    • So, do you have to talk to YOUR supervisor if your subordinate ask you out?

    • Only if I'm interested in going out with them.

    • Damn I like this job, pretty sure I could find a new one but I'd rather not leave, she is higher up so she has a lot more to lose than I do.

      And if I left that would really suck if she still said no anyway, but she seems lonely...

Have an opinion?

What Girls Said 1

  • Ask to go to lunch with her to talk about work.. Make up a reason. Like how to advance faster etc.
    disclaimer: you may jeopardize your job.


What Guys Said 4

  • She is your boss, it probably isn't going to happen. Her job could be threatened at most companies. If you were in a different department, that might be different.

  • It's unethical for her to go out with you and a risk for her in most businesses so the odds are shit and there's nothing you can do about that unless you can pay her current payroll.

  • This sounds just like the theme of a Mexican telenovela.

  • fuck her right in the pussy