Is it worth pursuing a woman your family knows? (20M, 19F)

Is it worth pursuing a woman that your family knows?

I’ve had this problem a few times in my life, and typically my answer has been “no, its not worth it,” but theres a recent scenario that has me rethinking whether or not it’d be worth my time to see if I should make a move.

In the past, I’ve always felt that it wasn’t worth the risk if things didn’t pan out, or didn’t even pick up at all. Frankly it’d be pretty fucking embarrassing actually.

Specifically, this girl is very well known by my ma, she used to work for her (she may still), and I’m fairly positive that my mother and hers are close friends.

A bit more specific, but the question still stands. It’s one I’ve asked myself a few times in my life.

TLDR: basically the title. Is it worth the potential embarrassment of a flop to go after a girl that your family knows?

1 comment
  1. Both of you are dating just 1 person and not dating their family.

    The problem isn’t her or her relationships with your family and vice versa. The problem is you and your relationship with your family and vice versa. Is your family the kind of people that interfere in the relationships of other family members? If they are you MUST insist on a boundary between your family and them meddling in your relationship and it will probably require a lot of effort on your part.

    It’s her job to advocate on your behalf with her family and maintain a healthy boundaries between her family and you and act on your behalf when her family treats you badly. It’s your job to do the same. If you can’t do that, none of your relationships are going to go well.

    If you think you can do it, ask her out.

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