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Should I tell this guy that I like him? How should I tell him?

Tagged as: Big Questions, Dating<< Previous question   Next question >>
Question - (15 June 2011) 3 Answers - (Newest, 22 June 2011)
A female United States age 30-35, anonymous writes:

My explanation is going to be excessively long, is going to make me seem extremely stupid and silly but I really cannot deny how I feel so please, please give me any thoughtful advice.

I expected this guy to tell me he liked me but he didn't and now high school is officially over for us both. This is the silly part. We have NEVER had a conversation with each other. We are also possibly complete opposites. He’s very popular and confident and if you ever saw him, you would probably stereotype him as the “bad boy” or, dare I say, “gangster.” He had a couple girlfriends before and well he has a reputation for partying. I'm not exactly socially awkward or unpopular. I'm not exactly your standard beauty. I dress well but I'm actually kinda short and chubby. I do not party, drink, or do drugs. I work very hard in school and I take fairly challenging courses. We only had classes together freshman and sophomore year where I shared a couple of honors classes with him. I’m not sure why he took those classes when he kind of slacked off. We have an entirely different group of friends. Mine and his probably never interacted before. In entire high school career, only one guy has publicly announced that he liked me and asked me out. I have never had a boyfriend because I just never felt confident with myself. Why am I so confident that this guy likes me when we never really spoke with each other? I know I am going to sound cocky but basically, he just stares at me. A lot, intensely (I know I sound ridiculous but you’re just going have to take my word). You can literally see his eyes looking up and down at me. We haven’t had a class together since sophomore year but in senior year, our classes were right across from each other. We both had teachers who pretty much allowed us to wonder around a lot. He always walks over to my class and peers into the window where we frequently made eye contact. And when I leave my class room to run an errand, about 5 seconds later he would come out of his own classroom and start walking across towards me and well, he just… stands there looking towards my direction. My friends who know about him and shares classes with him tells me that though he does do his work and gets pretty above average grades, he is really loud, a bit of a class clown and kind of defiant towards the teacher. Although when we shared classes together, he was actually kind of reserved and was pretty friendly and obedient with the teacher.

This might make me sound terrible but I wanted to test him a bit. I had 3 unverified period absents and it really bothered me. My school allows up to 12 but I just wanted to get rid of them. I decided to go to Saturday school with my friend. On the Friday before the day of my Saturday school, I saw him sitting on the ground possibly copying homework from his friend and I walked pass by him with my friend and spoke pretty loudly saying that I am going to Saturday school tomorrow. On the day of Saturday school, lo and behold, he was there along with me and actually sat right by me. You would probably assume he was there because he actually needed it, he does ditch a lot, but I checked the list, which listed everyone who needed Saturday school and how many truancies they have and he was definitely not on it. You could reason that he was there for his friends but after Saturday school ended, I saw him waiting outside for possibly his parents all by himself. Pathetic how ridiculous observant I am. I know.

To be frank, I really did expect him to talk to me on graduation day. I really did. Well, he didn’t. We then had an all night graduation event until 5am where we could not leave early. Again I truly expected him to speak to me. Well he didn’t… I am genuinely crushed over this. You probably ask why I like him when I never talk to him. All I can really give you is a clichéd answer. I have always felt a connection to him, since freshman year, ever since I heard his name. I didn’t develop a mild crush on him until end of sophomore year and it didn’t become serious until senior year, but he always stood out to me. I just admire his confidence and charisma. I want to get to know him, I want to talk to him, and I want to be with him. I really do. I really want to confess to him since he didn’t to me. Even if it is not true that he has feelings for me, I want an answer. I’m tired of having this little fantasy of me and him together. I need an answer. I figured that it’ll be ok for me to approach him because I am leaving for a college that’s about 8 hours away from my home and high school is over and if he did reject me, I can simply move on. The thing is I don’t really know how to approach him. I never talked to him. I don’t own a facebook. My friend has him added on facebook. What can I do really? Should I even do it? Please help.

View related questions: confidence, crush, drugs, facebook, move on, never had a boyfriend, period

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A female reader, anonymous, writes (22 June 2011):

I think you should definetly tell him because if you don't, there's always going to be that "what if" in your head for the rest of your life. I think that since you have graduated highschool already you can't tell him in a way that a high school girl would. (Eg. letter,anonymous note etc.). So I believe you should go up too him somehow, if you ever see him somehwere, and tell him that you were a little confused as to if he might have feelings for you or not. Then if he says yes you can tell him you have feelings for him too. Altough, if he says no or he "doesnt't know what your talking about", then just say okay thank you I just needed to know, and as you said,you'll have too move on. I hope all goes well with you! Good Luck!

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A reader, anonymous, writes (16 June 2011):

This is verified as being by the original poster of the question

Thank you so, so much for your answer!! I asked a few people for advice and yours definitely is the most thoughtful and it definitely read me really well. I actually have some more comments I'd like to add and I was wondering if any of it would kind of change your opinion.

1) What if he wasn't a player exactly? Like he just enjoyed partying? I haven't seen him with a girl at school since sophomore year and his girlfriends that I know of were always pretty classy and I never saw him engage in any PDA with them.

2) This might sou

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A female reader, CindyCares Italy +, writes (16 June 2011):

CindyCares agony aunt I would not say anything, what would be the point ? You are leaving soon for a place which is 8 hours away. You'll just have this summer for ... what ? A summer fling, best case scenario. If you are cool with that it could be fine, but, I don't know, something tells me that your little fantasy includes the possibility of developing a relationship with him , and becoming his girlfriend.

Highly improbable, since he is a notorious player. And, since he is popular with the girls and has confidence and charisma, he's not the kind of guy who'd have been afraid of approaching you if he really had wished to do so.

It may be that you picked his curiosity because you are so different from the people he hangs out with, - but he did not act on it, so it must have been something very superficial.

Better leave it as it is. You are infatuated with this guy because he is poised ,"cool" and self confident, qualities that you admire and you don't find in yourself.. Become self assured , and you won't need to be it by proxy through your men.

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