Been in a strange situation with a good friend for years - Not sure what to do

Sorry everyone super long post, I just really needed to get this out. I tried to write as best as I could to facilitate reading as much as possible and would appreciate if someone had the time to read the entire thing to fully understand the situation but I totally understand and would appreciate advice even if you’ve just read the TLDR because not everyone can take the time out of their day to read a wall of text. Also if this is in the wrong section please feel free to direct me to the right one.

TLDR My female best friend and I had feelings for each other years ago. I didn’t do anything but years later now, I like her a lot but I’m not sure if she feels the same way and I might’ve messed up by being too desperate/needy. At the bottom I’ve put a bunch of things I’m thinking of doing at the bottom of the post but not sure which of them is viable, I appreciate all and any advice.

I had a really strange NYE and I've been doing a lot of self reflection not knowing what to do. I'm open to all sorts of advice, so please don't worry about hurting my feelings. Also, some of the ways I describe myself might make it seem like I'm arrogant, but I'm not (at least I don't believe I am haha) I'm just trying to describe the situation as best as I can. If I do come off as brash please feel free to let me know.

I met my female best friend in grade 8. We had a lot in common and we hit it off. However, after a while I started to catch feelings. That year, we went to the graduation dance together, and she was always super touchy wherever we went. Her friends told me she liked me and told me to ask her out, and I liked her back. However... I did nothing

I'm honestly not sure why I never spoke up or said anything. I think I was insecure and not really ready for a relationship at the time. I thought she was too good for me, that she would say no (even though her friends literally said to my face that she would say yes) and most of all, I didn't know what to do in a relationship so I never asked.

We stayed good friends throughout High School but we didn't see each other much during grade 9 and 10 so I wasn't sure about her feelings towards me. Looking back it was super obvious she liked me in grade 9 but again, I didn't do anything because I was kind of insecure

Throughout high school I really worked on improving myself. I got a new haircut, started to dress better, hit the gym, made a lot of new friends, etc. I was having the time of my life in high school, I got good grades, hung out with lots of friends, and I was having a lot of fun.

Then, in grade 11 she came back into my life because we had literally every class together. I started catching feelings again but I wasn’t sure if she felt the same way. Looking back, she probably did but I guess hindsight is always 20/20. I should've said something, but even after all the self-improvements I had made, I was still afraid of rejection. I didn’t say anything the entire year.

The summer of 2019 came and it felt an arrow had struck through my heart because one of my closest friends (let’s call him T and the girl S) was crushing on her. He didn’t tell me, but I’m pretty decent at picking up social cues so I could tell. I was frustrated, since T knew that I liked that girl. I thought she liked him back as well because she was touching his arm, laughing at his jokes, etc. Then one day during August, she told me she didn’t like him at all and she thought he was creepy and he’d tried to ask her out multiple times but she said no every time. I was giving her advice while trying to hide my excitement. I was also the only person she told about her situation, which boosted my ego a little bit as in my mind I was (maybe foolishly) thinking that it was kind of like a boyfriend/girlfriend situation already. We hung out two times over the summer in groups and they went really well from my point of view, both times we went off on our own the two of us together and I personally had fun.

However, 12th grade came and I’m currently overwhelmed. I’m normally a straight A student without needing to study and was planning on going to university for applied science but all of a sudden, my grades were tanking. My mental health declined sharply and I ended up not talking to anyone in social media or real life and just studying to try and keep my grades up. I was super grumpy and not in the best of moods. As a result, my girl friend grew distant and I feel like she started to pull away and this is where I may have made a mistake. I started acting desperate and needy, I’d always try to start a conversation with her every single day after school, replied to everything she put on her snapchat/instagram story doing what I thought would keep her interest. I also did some stupid attempts at flirting which probably came off as creepy as I don’t think she found them super seductive or anything. I have a lot of female friends (and some of them have liked me but I never showed interest because I put this friend on I guess a pedestal if I’m going to be honest) but I’ve never had a girlfriend so I feel like that is where the needy mentality came from; I was so scared of “losing” her and just not wanting to graduate high school without ever dating anyone.

We attended a New Year’s Eve party my friend threw a couple days ago and something happened that I’m not even sure how to process now. We played pong together, won a few games against other people, and everything was going great. I overheard a conversation that she had with a classmate of mine about prom, and I heard her say “I think I’m probably going with H”.

H is my best friend and that crushed me even though I heard that out of context. I probably should’ve waited to hear more or not let it bother me, but I ended up leaving where I was listening from and drinking a lot since I was obviously feeling awful and as a result I don’t remember much from the night.

H has always supported my crush on her and he’s given me a lot of valuable advice this year so I’m not really sure what’s going on there; in addition H had the exact same thing happen to him that I supported him through where his girlfriend of two years went with someone else while he was still super interested in her so I don’t think he’d do something like that to me. Maybe they had a pact to go to prom together if they were both single by prom or something? They are very close friends and snapchat each other fairly consistently (which doesn’t bother me as I am very close with some of my other friend’s girlfriends as well but I obviously wouldn’t do anything to split them apart) so that could be the case but either way my mind is just running everywhere and it’s not putting me in a good mood.

Apparently I talked to a few of her friends while I was drunk about liking her and they all said that they like the pairing of us two together and support me. They weren’t able to give any advice because they told me she actually hasn’t talked to them about any guys at all since the 9th grade when she talked about me. However, I really don’t know where to go from here. I’ve thought about multiple different things I could do but I don’t know if they’re actually viable or not.

Where to go from here?

Confessing: This is what I was advised to do by her best friend. However, I’m not 100% sure about it as I kind of feel that it puts her in a position with a lot of pressure (Or at least that’s what I’ve read on reddit and it does make sense) in addition, two of my friends have done this confession thing to girls they’ve liked and it didn’t work either time. On the other hand, things might be different here. All advice about this is appreciated!

Ask her out: I’ve actually done this I think October? I was acting super desperate at the time so I’m not sure what she thought of it. I asked her if she was free on the weekend and wanted to hang out and she said she was busy. (She was actually busy that weekend she was out of town for a tournament) but she did not make plans to reschedule etc so I’m not sure how that went. Looking back I should have specified a time date and place and will maybe work towards that in the future.

Cutting her off:

I’ve honestly thought about not talking to her at all but we’re close friends and if any close friend (guy or girl) just stopped talking to me for no reason out of the blue I would probably be really pissed off and confused so I don’t know about this one. I know there’s some guys who will be super angry (think r/niceguys) if a girl doesn’t like them but I do value her friendship. Taking a step back might be hard as well because she’s moving across the country for university and the rest of this school year might be the last chance. (Hopefully not though of course)

Move on:

This one is easy to say, hard to do. I like her a lot and we’ve been through a lot together. All of my friends and her friends that I've talked to like us together. I would really like to date her and go to prom together but of course I know life doesn’t always work like the movies. I also think I would be hurt.

Working on myself:

I’m gonna do this regardless but I’m not sure if it’s enough. I think I need to work on having a better mindset when it comes to girls I have a crush on and not act desperate or needy and be myself. I have no trouble talking to girls and have many female friends, but as soon as I have a crush on someone my brain just shoots itself. Also, I think I need to work on being more flirty and not a simp because I find I do this a lot. Some of my friends are able to flirt super naturally but when I flirt I usually end up saying stupid stuff that makes me look bad. If anyone has any resources that helped them, advice, or youtube videos I can watch please send them to me as I am open to all sorts of learning.

Thanks for making it through this awfully long post guys. If you have something better that I haven't thought of I have an open mind and need all the advice I can get. It’s ok if you’re harsh with your advice, I’m not someone who can’t take criticism. Thanks everyone and hopefully a few months later I’ll be able to put a positive update on this post.

Ask her out: I’ve actually done this I think October? I was acting super desperate at the time so I’m not sure what she thought of it. I asked her if she was free on the weekend and wanted to hang out and she said she was busy. (She was actually busy that weekend she was out of town for a tournament) but she did not make plans to reschedule etc so I’m not sure how that went. Looking back I should have specified a time date and place and will maybe work towards that in the future.

- this is your answer. A girl who really liked you would make sure the date happened. A girl who likes you does not turn down dates.

The problem is, you never kissed her, you waited too long to kiss her. You got stuck in the friends zone. (that and you did not see her much for a couple of grades there, and with no kiss to kick off the relationship, her interest slipped.)

The next time you think a girl likes you, or you like her, hang out or date (same thing), and kiss her - that's what takes the relationship to the next level.

The big first kiss is one of the biggest moves in dating, but it has to happen - or it's definitely friend's zone.