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How do I ask out an OLD crush?

Discussion in 'Family, Friends and Relationships' started by Will, Mar 27, 2011.

  1. Will

    Will Staff Alumni

    So this is my first 'attempt' at this sort of thing. Up until a few months ago, I was in a relationship. I was in it since I was like, 14. I never went to High School; I home schooled through it. That being said, I haven't really the faintest idea of how to date, or ask girls out. There is someone I like...but we've never really hung out. She is mutual friends with my cousin on Facebook.

    I've 'met' her before, you could say. We went to Elementary and Middle school together. In 5th grade, she had a crush on me. I liked her back,but being super-shy then I never really talked to her.

    In middle school (7th grade) I still liked her, but had kind of given up on it slightly, because my severe lack of self-esteem back then. My 'friends' in Middle school thought it would be funny to date her even though they knew I liked her. So Jon went out with her for a week or something. It might be possible she was aware I liked her then, too. But anyway, that's...almost eight years ago?

    She seems like a great person, and I've always thought she was cute. I don't have any real-life mutual friends that I can connect to her with. I've been told where she works (a phone support center) and there's not really any way for me to just 'bump' into her.

    I think the ONLY way I have to contact her is through Facebook. I'm not sure how to go about it without being weird.

    How can I start talking to her, and ask her out?
  2. Prinnctopher's Belt

    Prinnctopher's Belt Antiquities Friend SF Supporter

    Through Facebook, you could send her a message and request to be her friend. "Hey, I know you probably don't remember me, but we went to school back at [] and I just wanted to catch-up with some old acquaintances. How have you been and what are you up to nowadays?" Hopefully she'll respond positively. Don't think you can just ask out someone you barely know though who probably won't remember you. See if she's currently dating or single, whether she has children, etc. Don't ask those specifically of course, just check her page and see if she's published that information. It's a good start.
  3. Will

    Will Staff Alumni

    Hey, thanks for replying :smile:

    Okay, that sounds good. She has published a lot of things for everyone to see, and she is single, etc. Now, I guess if you don't mind I'd like to ask you what you think on something real quick.

    So I'm thinking, could this be a little less creepy if I start friending people I USED to know from school in addition to her? Maybe so it doesn't look like I'm singling her out?

    Or maybe that's counter-productive and she won't blink twice at me.

    She has basically everyone from school friended already, and friends more maybe once a week or so. I think if I can word this right, she might actually accept.

    I guess my next question is, if I get her as a friend, how do I socialize in a non-creepy way?

    I've figured to not ask her out right away, and what not. But she's not Facebook very much, maybe a few times a week. Any ideas?

    Thanks again.
  4. Prinnctopher's Belt

    Prinnctopher's Belt Antiquities Friend SF Supporter

    Don't look too much into it. All you're doing is friending her on Facebook. Nothing weird about that, especially since the two of you already share a network. Sure, friend some other people you knew back in the day as well, but not for the sole purpose of giving the appearance that you're not singling her out. Do it to connect with others. Maybe there will be an event you all could go to together.

    How to socialize? Well do you both live nearby? Use your senses. If there's something going on, get together with a couple of people you already know (if any?), and invite her. "Hey there's this thing going on, and I'm going with a couple of my friends. You're invited if you have some free time on your hands and you don't mind". The purpose of inviting someone new to an event where you're already joined by other people you know, is so that it's less intimate and it doesn't seem too personal or awkward. And it allows you to have some casual conversation and check if you're feeling the person enough to decide to date her.
  5. Will

    Will Staff Alumni

    Maybe this is my real dilemma.

    The one network that I have with her, isn't very much important to either of us. My cousin goes to college 2 hours away, and he does not hang out with her, or her crowd period. If I get her as a friend, I'm not sure I have any channels of communication to her.

    I don't have all that many friends period, and none of them are even close to knowing her. She lives...or used to live 5 minutes away. She lived on the same block as the school. I don't how true this anymore, because she posted that she moved (<2 weeks ago).

    My thoughts currently are, even if I can make absolute small talk on the occasional Facebook chat, how's that gonna progress to a date at any point?
  6. Prinnctopher's Belt

    Prinnctopher's Belt Antiquities Friend SF Supporter

    You'd eventually have to go out someplace where you can finally meet. I don't know how that would come about, but you could say "hey there's this thing happening in town and I'm going. You're invited if you wanna come along and have some free time on your hands. Maybe we can catch up since it's been so long since we've talked and you probably only barely remember me, lol. Let me know if you'd like to come."

    It's already odd that you're trying to hit on someone you don't know through Facebook. So find something fun and interesting, invite her to join you. The worst that can happen is she'll just say 'no' and you'll go anyway.