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Please help me find a way to ask him out

Tagged as: Crushes, Dating<< Previous question   Next question >>
Question - (7 December 2015) 2 Answers - (Newest, 11 December 2015)
A female United States age 26-29, anonymous writes:

Hi agony aunts, my question seems really silly but I seriously am clueless about approaching a crush and getting to know him better, and well anything that has to do with relationships honestly.

Basically I am a senior in highschool and I have a couple of classes with this guy I like. I've had my eye on him since I was a sophomore but I never really talked to him until junior year, and even then it was because we happened to hang out with some mutual friends. Fast forward to the beginning of senior year, I realized I had two classes with him and apparently he noticed me too. He brought up what happened the year before (we all almost got in a lot of trouble together but we're able to sneak away before we were caught) and ever since we had started talking in class and around the halls. There really isn't any awkwardness between us, we will say shitty pickup lines to each other, make sexual jokes, talk about many common interests, and he has even told me a lot about his childhood. Now that explanation seems unnecessary but the point of that was, even with being that comfortable around each other, I still can't gather the nerve to ask him for his phone number and obviously he hasn't asked me for mine. I was really wondering how I should go about it. Should I just ask him up front or try to drop some hints or should I just wait until he asks me. Also how should I approach the fact that I like him, I really want to date him but I feel like it would be horrible if I asked him out on a date. I really have no idea how it works for relationships since the only one I've had crashed and burned after a couple of weeks. Sorry this took so long but thank you for any advice, whether it's about getting his number or dating, anything is appreciated!

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A female reader, aunt honesty Ireland +, writes (11 December 2015):

aunt honesty agony auntI can see how daunting it could be to ask him for his number. You say you have cheeky conversations, so maybe slip it in to one of them, when he says something to you maybe laugh it off and say aw well if only I had your phone number I could tell you my answer later. Something casual like that.

If you cannot find the nerve to do it, and don't worry if you can that's okay because many people struggle with this, then maybe you can look for him on social media and communicate through that.

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A female reader, anonymous, writes (7 December 2015):

Hi there!

I have a similar problem. I've liked a guy for years, but I was socially awkward and shy and never told him about it. And I regret not telling him. Because now he has taken a different path and I am slowly disappearing from his life, even though he is still everything in mine.

If you really like him, don't hesitate to tell him, because if you never ask, the answer will always be no.

Many people exchange numbers casually, so if you ask him he might not even be hinted about your feelings. Definitely ask for his number, then casually chat, try to be a good friend and make him see what a cool person you are and great girlfriend you might be. And ask him out if he doesn't first and you feel like it's about time. Just be yourself when talking over the phone or on dates, like you always are around him. No point in pretending to be a flawless goddess and disappointing him later on because you aren't really one.

My best wishes for you!

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