With 2 weeks left of Senior year should I finally make a move or just let it go?

A female age 30-35, anonymous writes:

So there’s this guy who has liked during High school and possibly middle school too, the typical staring, trying to walk close by me in the hall and hair fixing. He’d always been someone I was attracted to but somehow we were friends with the others friends but never directly with each other and knew generally how we were from that. However we are both really shy [him way more reserved than me] and after two years of nothing, even when I had a mutual friend tell him I liked him, I got real frustrated and pretty much gave up when my best guy friend and I started a little romance because I figured it could lead to something great whereas me and my crush had yet to have a legitimate conversation. Though I told my friend I was over him and really did develop feelings for him, the guy I liked always stood out to me and I wondered if I was making a mistake in giving up, also during key steps in the relationship like the first kiss, holding hands etc. I always asked myself if I would’ve felt more if it was him. I felt really guilty for that but figured it was just because I was used to liking him for so long and is also why I was so tolerant of my friend talking to his ex which turned out to be a huge mistake. He was trying to get back with her while stringing me along and I figured since I wasn’t completely over my 2yr crush I could understand his trouble with moving on from someone he shared a 3yr relationship with. [I know stupid] so I forgave him and he ended up screwing me over for her again. That’s done and over with. I kept telling myself “Nice, I traded someone who truly must’ve considered me something special for a total asshole”. I refused to immediately go back to perusing my crush because it felt wrong after 1.) I said so often I was over him 2.) I kept telling myself I made a choice and have to deal with the consequence. That was 2months ago and last Friday we had senior breakfast and my crush sat with us and two of my best friends said every time they looked at him he was looking at me. So I finally talked to him and teased him for being so antisocial and he talked back with the biggest smile. Throughout the day we had a barbeque in the football field and I would make remarks and he would laugh or smile as he replied. However this week its back to the usual routine of us passing in the hall and he glances but says nothing. So now there’s only 2 weeks left of school before graduation and I’m telling myself do I really want to let this guy be the one that gets away? Yet I don’t know what I could do. Wouldn’t it be weird if I just went up to him and started talking or just told him I was interested? I have no clue on how to initiate conversation with him. I was told I should start off by smiling at him for 2 days or so then throw in a hi. Yet to do that and then be like ‘Oh hey I like you’ seems even more odd. All that comes to this: How should I go about approaching him finally? Would you feel awkward? and is it even right pursue him again?

View related questions: best friend, crush, his ex, shy

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A male reader, goalstopper  +, writes (26 May 2011):

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