This is going to be a long one, I’m going to include all pertinent information so please read the whole thing, then give me your advice. Please forgive any grammar errors, I am on mobile.
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I have never dated a girl, asked anyone out, and until this year had no clue the opposite gender was even attracted to me. I’m getting more comfortable talking to girls, but not really flirting or anything like that- yet
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I have friends- just not the kind you hang out with outside of school, mostly through sports, and when I do get invited to functions it’s usually a one time thing, but this isn’t r/socialskills so I digress. I’m working on it, I just wish I actually got invited to the stuff my friends go to, ya know?
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X, the girl I have a crush on, has never been in a relationship afaik. I am not the only guy crushing on her/ wanting to ask her to dances but she has so far stayed single and I’ve never heard of her having a crush on a guy despite my close connections with her.
It is the fall of my freshman year. I am crushing on these two girls who are in my study hall. One of them, blondie, plays the same sport I do. One day, they are whispering about me and tell me to come over. I do, and they ask me if I am taking anyone to homecoming. After I say no, they ask me if I know this girl, let’s call her X. X plays the same sport as the blondie and I [soccer], so I recognized her name but had never met her. The blondie and the other girl then suggested I ask X to homecoming. Looking back, I don’t believe this was X trying to get a date with me by using her friends, I believe it was just blondie and her friend trying to play matchmaker. Anyway, I start to look X up on social media to find out more about her. After about a week, I had developed a full-on crush for her. My friend Mitch, who was going with blondie, was getting a group together a group of girls and another one of my guy friends. He invited me to join, assuming I was going to ask X to the dance. I said sure, I’m probably going to ask her. Here is where I may have fucked up- I [following my older sisters advice] asked a mutual friend of X and I’s to ask X ahead of time if she would say yes to spare any embarrassment between the two of us if X was going to say no. My friend came back with bad news- sorry, she’ll probably say no [i have no reason To think mutual friend lied bc she liked me, she was dating at the time and already had a date]. So, any confidence I might’ve had was shattered, and I ended up never making the sign, and never actually asking X. I still went to homecoming with X in my group, I was the only guy without a date and X+ another girl were only girls without a date. During the dance, all but the freshmen just grinded and being young and naïve no freshmen actually danced with partner or anything, so everyone in our group spent 2+ hours milling about increasingly getting weird because nobody was talking or dancing. After dance, nothing happened, went to house with group and got food then went to Mitch’s house and went to bed. We had another dance in the winter, but traditionally girls ask guys so I just waited and waited and waited...
Enter sophomore year. Whereas last year, I had no classes with X, now I have 2. I started playing football over the summer as a kicker so the combination of the soccer and the football workouts gave me a nice six pack and some good muscles. I was in the best shape of my life and a starter for varsity Football, as well as being a Junior varsity captain!!! One day, a few weeks before homecoming, I had an idea. At my school, every home game the varsity players give their away jersey to their gf or mom or sister or homecoming date to wear to school/the game. I wanted to ask X to homecoming, so I gave her my football jersey to wear in what was the clearest indication I’ve ever shown her I liked her. She wore it to school, and I asked her if she was going to the game. She said she didn’t know, so it would be better if I just took it back at the end of the school day [since she wouldn’t be wearing it to the game] . I got my jersey back at the end of the day, but then X ended up going to the game. So that hurt a bit. One of my closest football friends who was friends with X since elementary school knew I wanted to take her to homecoming (I told him and asked him for some advice) I guess he decided to test the waters for me because during warm ups he told me that he tried to hype me up to X during one of the classes, asking if she wanted to go with me, talking me up, saying I’m a great dude, etc. What he said next stuck- “Just don’t. It’s a bad idea [referencing me asking X to homecoming]” this once again crushed me, I didn’t ask X, and I guess she went with a group of her girlfriends. 2nd semester I get put at a table with X, her best friend [call her Bestie], and another of their friends. The class was easy and I started to become friends with all of them. By the end of the school year, I was conflicted- I cared for X on a level that was more than just physical attraction; our friendship had only confirmed I liked her mind as well. Over the summer, just like last year, I just lifted, went to soccer, and football, traveled around, and still I got excited walking by a girls soccer practice because then X might be there.
We didn’t speak all summer, but then again we weren’t really that close and I don’t really have any friends , but enter Junior year which is where I am now. I entered this year after a long summer of travel and sports, ready for a challenge. This year, in addition to soccer and football, I am taking 5 AP Courses and studying for the ACT all while doing college visits and trying to do some community service. I still have plenty of flexibility to hang out with friends and I get kinda sad when I see “friends” doing stuff without me when I’m home with nothing to do. I have 3 classes in a row with X, and spend about 45 minutes a day at a table with her and Bestie, along with 1-2 other friends usually trying to study but just gossiping, talking, doing puzzles and generally just being friends during a study hall. This year for homecoming, I kinda accepted the fact that X probably didn’t like me [based on the last 2 years] so I just did nothing and she went with some random dude so she could go with her friend group and party. I’m not jealous or worried she likes him, she’s pretty much swerved him and doubt they’ve talked since homecoming. I had a girl ask me 2 days before homecoming if I would go with her and I said no on account of the fact there was no way in hell I was going to find an outfit on that short I’d notice and I didn’t like her that much [yeah a bit of a dick move but hindsight is 2020 and I did my best to let her down easy, she ended up finding a date]. Couple weeks later and I hear (I forget how) that one of the sophomore soccer girls (SG for short) had a crush on me. This girl is closer to my type, but back in October I still had my sights set on X, so I kept her at arms length. I Snapchat sometimes but idk if she’s still into me. Anyway, back to X. When one of my football friends told me that SG had a crush on me, I had no idea who she was. I asked him a bit about her as we cleaned up the athletic training room training room and I told him something to the effect of “I’m not just going to pursue someone I’ve never met before... I need to get to know them as a person before I can decide if I am attracted to them.” This was while one of Xs closest friends was in the room with us and was helping clean, staying silent so obviously listening to our conversation about SG. Anyways, a week or so later, I am driving a friend home from school and waiting for him in the lobby. X and her friend from the training room are there. It just so happens my friend I was driving home was having some relationship issues so I was doing my best every day on the drive home to listen and give advice as he decompressed. He randomly asked me how my dating life was going. I told him about SG and X, and kinda subtly pointed X out to him as I explained she is the one. He was like aww, nice man, but then something happened. X kinda just smiled at me and said “hello” or “hi” with a giggle after training room girl quietly talked to had about something. Now, about once every two weeks, [this has only happened 2-4 times] she’ll look at me in a way I’ve never seen her look at someone else. Does stuff like drops a conversation to say hey then giggles or smiles [she doesn’t snails much]. X has also become a bit more playful, friendly teasing me and the like which was previously not a part of our friendship. When she was driving by as I walked to my car, she honked and hit the gas, scaring the shit out of me. Playful, friendly stuff that only happens so often but gives me hope. I don’t want to be the guy that misreads friendships as “she’s into me”, but I also don’t want to be the guy who never finds out his crush likes him back and lives happily ever after.
Here is the big dilemma, and the conclusion to all of this- the more I spend time with X, the more my attraction grows to her as a person and as a friend. I know the obvious answer is to just tell her how I feel, but I want to keep her as a friend because she and Bestie would probably both be gone if things got weird and they’re some of the closest friends I have right now. The past doesn’t look good, which is why I’ve held off just letting her know or asking her out. But I can’t go on like this forever. It’s not fair to me to have to turn down/ put other girls like SG on hold while I try to work out my feelings over X , or for girls like SG to date me while I am not emotionally invested in them. I just want to get this situation resolved before prom and or winter formal, I’m tired of skipping dances and want to have some fun before high school is over, X becomes the one that got away and SG gets mad for my non-reciprocation.
Thank you so much for reading this wall of text, but now that you’ve read it, you know more about my life than literally anyone else in the world.
TLDR: girl I like has kinda sorta denied me 2x in the past, but now I’m getting some mixed signals. “Just tell her” probably won’t work unless she somehow likes me too; I really really want to stay friends.
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