Is it too weird to ask this girl out? Sister of a new friend of mine, but both old acquaintances from high school. Would that be awkward?

So, I grew up in a smaller town where most of my friends have to move to find a successfull career. I live in a bigger metropolitan area about 3 hours away and recently a bunch of people I used to know from high school moved here as well. So here's the dicey situation. I just joined a new gym to start working out with one of my friends from high school who is now in med school. We never really hung out or knew each other that well before, but whatever. So his one year younger sister lives here and is in nursing school. Hold on it gets even more dicey. I have another friend here in med school that I hang out with every now and then. We chat about hunting and whatnot. Anyways, He dated her for like 3 years back in college, but is now married so another girl! Keep in mind I never really hung out with these acquaintances back in high and I went to a different out of state college, so I haven't seen them in years.
When I first ran into this girl recently it was late at night at a chill bar and I was hanging out with her brother.
Would it be weird to ask this girl out since I've started working out with her brother and she used to date another friend of mine? Should I ask her brother if it's ok first since we have started to become friends?


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What Girls Said 1

  • No, it's not awkward. You're interested. You like her. Make it known before another guy swoops her. It IS polite (and kind of traditional) to ask the brother if he's fine with you dating his sister. To get brownie points, I would go ahead and ask him. :)

    • True. Yeah I figured asking her brother might be a good thing to do haha. Should I ask her brother for her number, ask her out on FB or just wait until I run into her again? I don't run into her very often so that could take awhile.

    • No! Lol. Just see if it's okay with your friend if you can date his sister. After he says yes, I would personally go to her.

      You don't want her to suddenly feel creeped out/affronted that you got her number from her brother and didn't consult her about it (there are women out there like that). I would simply tell her face to face that you're interested in her and would like to take her out sometime.

    • Haha alright. Thanks for the advice!

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