Contacting an old high school crush?


Contacting an old high school crush?

  • Hayley Matthews Hayley Matthews
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    February 17, 2013 at 6:19 pm #22857
    Contacting an old high school crush?

    Okay, here’s my story.

    Back in high school, I had a huge crush on this one girl for a couple years. She was always on my mind. I was the typical socially awkward guy that
    didn’t really know how to deal with girls that I liked yet, and so I ended up screwing it up. I was always super nervous
    around her and never really had a conversation with her. Basically, I ended up sending her
    a Myspace (Facebook wasn’t cool yet) message telling her I liked her (in hindsight, an obvious bad idea, but I was awkward back then), and it went downhill from there. I had hoped that it would
    maybe help to make things easier to get to know her and then she’d notice me too,
    but it ended up making every future situation with her awkward for her and me. Eventually she told people and a lot of the school found out too. I went through high school never asking her out.

    Fast forward to now. I’m finishing up college this year and have had other relationships since high school. I’m a lot more confident in myself,
    and have really come out of my shell I guess you could say. I’m more fit, social, and I’d say better looking than I was then. Basically, I’m
    not the awkward high schooler anymore, but someone who knows who they are and has a sense of direction in life.

    When I went into college, I tried my best to forget this girl, and until recently I had done a good job of not really thinking about her. I
    dated other people, lived the college life, worked hard, etc. But in the back of my head, its always been a “what if” scenario and
    I’ve always regretted that I never even asked her out. And lately, I’ve been thinking about it a lot more and feel like I need to do something about it.
    That’s what is really bothering me, that I never really took the chance. And I think that if I hadn’t handled things so badly then, we would’ve at
    least been good friends. I do genuinely believe that there could’ve been something if I hadn’t handled it so awkwardly. I’m not a bad looking guy, I’m funny and fun to be around, and people generally like me. She never saw that side of me, just the guy who liked her but never talked to her.

    With college coming to an end for both of us, we’ll probably be going back to our hometown for a while. And honestly, I really want to see if
    we could actually work as a couple with me being more confident than I was back then. I checked out her facebook profile and she is definitely
    single. I am still attracted to her (but its not like putting her on a pedestal like I probably did in high school) and feel like maybe she’d
    like me if we got a chance to have a conversation or date.

    So, I would like to finally ask her out. If I was certain to run into her, I wouldn’t have a problem with that and would be able
    to have a good conversation with her, but there is really no
    guarantee that I’ll bump into her or anything. So what could I do to re-establish contact with her?

    So here are the obstacles:
    We haven’t talked at all since high school (4 years ago) and even then, they were short awkward moments. So I do think there needs to be
    some way to re establish contact with her. If I don’t see her in person, how would I do this? Facebook seems like a possiblity, but
    without the face to face interaction I feel like it might come off as obvious or creepy.
    I don’t have her number, so contact by phone is a no-go.
    And I feel pretty certain that she does remember who I am, meaning that if I contact her there is that risk that she’ll assume
    I’m still crushing on her and might feel awkward talking to me.

    I just don’t know how to approach this without coming across as a creep.
    I really don’t want to regret never asking this girl out for the rest of my life, and I feel like I need to do something about this or else I’ll keep thinking about it. I do think that there is a chance we could work if I managed to
    successfully show her that I’m a different person. And at the very least, a date with her will give me some closure even if it doesn’t work out.
    So does anyone have any advice as to how I can reintroduce myself, and try to make something happen?

    I greatly appreciate any help you guys can give me.

    February 19, 2013 at 6:29 pm #23098

    Go the Facebook route. Learn to summarize your feelings, I think I skimmed half of your post because I knew exactly what you were going to say. So. Simply put “hey, it’s so-in so, I reached out to you through myspace 4 yrs ago and obviously had no idea what I was doing when I messaged you. I was a bit embarrassed but after so much time has passed by, you came up in my mind (don’t tell her you’ve been thinking about her for 4 yrs, that’s creepy) and I wanted to reach out to you again. How are you? I see you’re still involved in ____ (sport/activity), still going well for you? Anyway, just wanted to say hi again, and see if you’d like to catch up sometime when we’re back home for break. Take care.”

    My point is, briefly state why you’re messaging her, don’t make her feel bad for you. Give her a compliment or ask her something about what she’s up to and then leave the ball in her court that you’d like to meet up in the future. It could be a slow start so don’ expect her to come running into your arms. You have to be friends with her first. you’re still strangers. I think the worst thing people do is put these high expectations at the beginning of a spark…take it easy. She’ll admire your honesty. Don’t be pushy and rush anything…

    March 10, 2013 at 11:25 pm #25396

    You say that you regret never having asked this girl out but isn’t telling her how you feel in an e-mail pretty much the same thing? After all, if she got your e-mail and she was at all interested in you she would have told you as much. I think your are just still hopelessly hung up on this girl and you have somehow convinced yourself that, even though she was not interested in you back then, she will be now due to your new found confidence. I’m afraid you have fallen into that trap that so many men and women fall into where you are saying to yourself, “if only I had done this differently or said that differently she would like me” when the truth is probably nothing you could have said or done at the time would have made the slightest difference. Also, to be honest, if you were really as confident as you think you are now you would not be worried about “coming across like a creep” when you again try to approach her. When you can go up to beautiful women and talk to them in the same relaxed manner that you would talk to your best friend, not having the slightest worry about saying the wrong thing, then you will have achieved true confidence. And if you can do that, these women will always respond to you in a positive way (they won’t think you are creepy).
    Anyway for the time being if you want to communicate with this girl the best thing to do is contact her again in FaceBook, only do it in a very upbeat and casual way. Don’t tell her how you feel. Don’t try to explain away your awkward High School attempts to get to know her. Don’t talk about possibly meeting up at first. And don’t try to “sell” yourself. Just act like you stumbled across her profile and was wondering what she’s been up to. You’re just a confident laid back guy who wants to shoot the breeze with her. Then, if you can build up a report over time and get her laughing and enjoying your communications, then and only then should you talk about going out, and even then, only in a casual way, like going on a hike or something. You left this girl thinking your were a creepy stalker in High School so the only way this will work now is if you play it cool and don’t move to fast. And definitely don’t let her know that you think you are in love with her.
    Anyway I hope that helps.

    August 3, 2016 at 2:51 am #107300

    So Cobbler, I read your post because I’m pretty much experiencing the same thing except my story begins in middle school. In middle school, I was too a shy kid who barely talked to strangers. My class was fairly small so I pretty much knew everyone in my class including this one guy who I was completely nuts about. Anyway,of course, I had acne and other insecurities and just looking at him was hard plus my personality is just really awkward. Fortunately, my sister was friends with his sister so we kind of hung out because of their friendship. We got along for the most part but I feel like sometimes I was mean to him in order to hide the way I really felt. After the first semester, I felt like we were going to be best friends or something more. However, the next semester a new girl came to school and she just happened to be his best friend from kindergarten. At first, I didn’t think it was that big of a deal, in fact, I became friends with her. But after we became friend she started

    August 3, 2016 at 3:04 am #107301

    telling me how much she was in love with him! I was crushed disappointed and confused. At that point, we had become good friends and so I tried to stop liking him for her sake. It didn’t work. In the end, I had to leave that school but I desperately wanted to talk to him. So I happen to see his number in the girl who was in love with him since kindergarten’s phone, I memorized it and then put it in my contacts. Later I texted him and this was the embarrassing part because he didn’t recognize my number and told his mom. His mom freaked out and told me to never call again. She did not know it was me so I understood but I was super embarrassed. I never wanted to see him again after that. Fast forward many years, I happen to run into my crushes mom at the supermarket! My heart dropped. By the way, I’m almost 20 so I tried to act mature about seeing her. We talk for a while and then she gives me her number and her daughters then she says oh you probably don’t want my son’s number.

    August 3, 2016 at 3:17 am #107302

    I stupidly say no. Now you’d probably think wait! you already have his number! But no, it was changed probably due to the fact that I kept accidently calling him. So after we had said goodbye,( his mom and I,) I immediately regretted not getting his number. HIs mom had told me that he was going through a hard time making a decision about school and I feel like this why we reconnected so I could talk to him about it. Now I have to figure out if I should call his mom and then ask to speak to him or go through his sister. If I go through his sister, I’d feel like I’m going behind the mother’s back which is not my intent. But, if I call the mom she might be leery letting me talk to her son. Ugh, it’s so difficult, but I feel like I need to talk to him. Also, I think you should send your crush a friend request if she accepts then you have hope. And when you message her don’t start off heavy. Just be like hey! long time no see, and see her response. I wish you the best!.