What to do when your boss is coming out with you when you ask her out?

Hi, everyone how are you doing? Well I have a sweet dilemma. I asked my super cute boss out after reading all of those signs and she said yes.

I am prepared man so I know what I am going to do for a date but the thing is my boss makes more money than me and used to the authority over me at office.

Would it be okay if I pay for everything? She would not take it in a wrong way right? I know she is just my date outside of the office but should I mind if she instruct me in someway because of her daily routines in the office.

How much instruction can be counted as a result of some daily routines. For example if I want to go to the my bar but she wants to go to her bar. She did say that I should stop her if this happens but you know girls. Would it hurt her ego in someway? She is super professional so she would keep it outside of the work as far as I know but You know what I mean?

Anyone with the similar situation?


Most Helpful Guy

  • Away from the office she is not your boss and you should behave exactly as if she is a supercute girl you are dating. Never mention the office, she wants to get away from the persona and the rules imposed on her by her job, which may be isolating her from the social contact she needs. Back at the office, she is boss. As her date, you are boyfriend/escort. Keep it informal and relaxed. Again, forget the office when you pick her up.

    • Yeah exactly, actually I just received the text from her that please treat me just a normal girl who wants to spend quality time with you. Just don't worry about anything. Whatever happens happens. Just don't discuss things especially if we do anything beyond bar together (at any point) at the office to anyone. If you do it will be an end of seeing you.

      Does she mean sex?

Have an opinion?

What Girls Said 1

  • It doesn't matter that she's your boss at work. She's your date when you're on a date. Treat her like you would anyone else


What Guys Said 1

  • Don't try to buy love or compete with her.

    Don't worry about an accidental "boss mode". If it happens a time or two, it might not be a big deal. If it becomes a problem, then just gently let her know.

    Humility won't make you less of a man.