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So here's the situation I'm in. I have this friend from High School. We didn't really start to hang out until maybe halfway through senior year. She had a boyfriend at the time but eventually she didn't and I was into her, but never made a move because 1) betaproblems and 2) we were gonna be leaving for college eventually anyway. We stayed in touch a bit and occasionally hung out during breaks.

 

Last weekend I had my five-year high school reunion. It was the first time in about a year that I had seen her. We talked and joked and it was good. I'm going to be seeing her on Monday to play some tennis, and when I do, I'm planning to ask her to a Twins game.

 

tbh this is the point where I should stop thinking, but I'm not going to. I can't help but try to over analyze this before it even happens, and that's a major flaw.

 

I've never asked her out on a date, which is my intent here. Whether or not she'll pick up on that, I don't know, but I'm assuming she will. But since we've been friends for a while, I don't know for sure. I'll try to figure that out based on her reaction. I know it's possible that she'll ask about my intent and I'll tell her.

 

But it's if she doesn't that is where I am stuck. Do I bring it up right there? Or do I wait until the day of and bring it up after (if I felt good about how it went)?

 

 

Obviously situations will differ based on the people and the exact nature of the relationship between them, and since you guys don't know these things, you may be unable to help. I don't really know what I'm looking for from you, maybe just a general idea of what you think I should probably do, or maybe just words of encouragement. idk, but just talking about it makes me feel better about it.

Edited by Streetlight
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And watching Shia LeBoeuf motivation video did help?

yea

 

Thanks be to Shia, I did it.

 

I listen to Shia every morning. That's a lie. I'm sorry I lied. mfw :(

Edited by Streetlight
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Yea,

 

Honestly, go for it. If you don't you'll spend the next 5 years wondering what could have been until you get to your 10th year high school reunion and find out she's married with a kid.

 

It may be 2-3 minutes of awkwardness, but you have to sometimes just put yourself out there. So straight up ask her to the Twins game as your date. That's my honest advice

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Just do it, the worst thing she can say is no and if thats the case fuck that shit, life goes on my brotha. Plus if worse come to worse, ill go to the game with ya street

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I find it helpful to remember that there's not a lot you can do to influence how she feels. By that I mean, either she likes you in enough of a sense that she would date you, or she doesn't. Normally I wouldn't be too forthright about the "date" word and just go for drinks or something, but since you've known her for quite a while I would say that you ought to.

 

So say something to the effect of what Mrs. J-Gow suggested, and if she accepts and she touches your knee later, that's a great victory.

 

But if she says, "Ahh, I like you, but as a friend," then that's fine too. You can shrug and be like, "It's cool, I was just checking," because really, that's all you are doing. Maybe things will be weird with her after, but whatever, you spent most of college apart, and that's what she gets for being cool and diggable. But now you know where you both stand and you can resume life and maybe touch one of her friends' boob.

 

Either way, you tried, and there's no bad way it can really play out. Awkward, maybe, but we're awkward people. We can handle it.

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