Can I ask a guy I knew in high school out if I haven't been in contact with him since? Please help me and I'll answer yours too, thanks?

Okay, here's the situation: I go to community college and so does a guy i knew in highschool. He was always so so shy, albeit sweet, and I was very outspoken, a cheerleader, and I also had a 'sweet girl' reputation. I got to know him on the grad night actually, during the party afterwards. I asked if i could sit by him on the bus and we hit it off so naturally and effortlessly like i'd never had before or since, and i ended up falling alseep on him totally not trying to flirt or anything and he didn't wake me up and draped his jacket over me. Gentleman. I was kinda sad the next day that I hadn't gotten his # and I looked him up on social media which HE DOESN'T HAVE. -_- So I chalked it up as a loss after asking around and no one had his number or anything.

So a week ago (It's been 2 years) I saw him at my college and was unable to catch up to him before he went in a class. So naturally I stalked the heck outta him online and found zilch. I think I can catch up to him maybe, if i time it right, but I'd only have one chance to talk to him. I don't know if he has a girlfriend, or if he will be transfering, or if he even thinks i am attractive so I'm wondering what I can say in a one minute conversation to ask him out/hang out that wouldn't scare a super shy guy away and make him feel really uncomfortable. I would go to his friends but i don't know them well and only keep in contact via social media and it would feel weird being like "hey remember sophmore biology oh and give me your cute friends number"

  • Get his # from his friends like a stalker; regret it for weeks before using the #
    Vote A
  • Ask him out in person, but it's gonna be awkward *evil laughs & pointing*
    Vote B
  • Move on lady go get some cats or something
    Vote C
  • I'm just here for the free popcorn.
    Vote D
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Most Helpful Guy

  • Don't ask the friends...

    Look, you know where his class is. Truthfully, he doesn't know that you have noticed him yet. Just casually bump into him on his way to class. "Hey, you look really familiar..." Just go from there. Act stupid and then ask him about his high school, etc. Lol, it's easy as pie.

    The one thing you have going for you is that you're a chick. Guys are more receptive to chicks even if they are strangers. Sadly, chicks do not return the favor, that's just how it is lol. So, Go for it. Bump into him.

    • Alright, thank you! It is unfortunate that boys tend to put themselves out there more than girls, I've made an effort to ask guys out myself so that I am not limiting myself to 'hinting' and it is so scary! You boys are freakin brave

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What Guys Said 2

  • I think that ask one of his friends is a bit like stalker (well, who knows), so i would say that you should ask him personally...

  • You should definitely talk to him!!! I reckon if you don't you will regret it!

    • Also this is the second time you have asked about this so you will for sure regret it if you don't talk to him!! :)

    • Show All
    • I honestly burn so bad, and don't believe in tanning beds so its self tanner and sunscreen for me! And i also walk in heels like a sad little calf. I got this profile when i was younger and I know people in real life on this site and don't want them knowin my buisness so here are some hot chicks feet *boom* for everyone to enjoy

    • aha yeah if I wanna tan I have to use that stuff as well aha my sister laughs at me for it even though it was her idea for me to do it aha. Walking in heels is hard work aha Its almost like a workout after a while aha. and thats completely fair thats why I dont have a picture on here aha. I doubt i would actually know anyone anyway.

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