I (20M) went to the same high school as this girl (20F), where I had a crush on her for the majority of it. We never really talked to each other much as we were both very shy, but I always thought that we were really compatible, and I was really in to her. Needless to say, I never asked her out as I was way too scared. It wasn't until about a year after university where I found out from people that she had actually liked me too. The news was bittersweet however, as I knew she had a boyfriend at the time so I knew I couldn't reach out to her.
Fast forward 2 years and I'm finally getting to a breaking point. Due to me still being a shy and passive person, I've just had been hoping for the perfect moment where I could run into her, and then build up a connection with her again naturally. Unfortunately that hasn't come. I am lucky enough to go to the same university as her; however, it is incredibly large so I hardly see her, and whenever I have its in passing, so we only exchange brief 'Hi – how are you?'s. Next year will be our last year at the same university, and who knows what happens next so I'm really starting to doubt whether I'll have that opportunity I've been hoping for where we have the same class, or study in the same place etc… where I could initiate a natural prolonged conversation.
I hate how I was so shy for almost all of my life, and all the amazing opportunities that have passed me by because of this, so part of me thinks to forego all this waiting and just DM her. However, I am aware of how bad/weird it looks to be messaging someone that you haven't talked to in a while. I am aware of the very real possibility that she doesn't have feelings for me anymore, or that she might think that I am getting desperate and just messaging random girls from the past. If either of those are the case, or if she has a boyfriend (no longer with the old one, but can't tell if she is with a new one) that could lead her to block me on social media/not reply, or just overall start to think poorly of me. Which would then ruin my chances of then building that connection with her in person. I also run into her friends occasionally (only ever have small talk with them) and I know that they'd view me differently.
I am torn whether it is better to just message her and hope she replies (small chance IMO, as messages from people you haven't really spoken to in years don't really get replied to), or I can just wait like always and hope that we have that elusive natural conversation, which would likely have a higher success rate of building a connection, but small probability of happening. Part of me knows that I blew my chance; but to some extent I just want to know for sure, and end all of the what-ifs in my head. I just don't know whether that's worth blowing a hypothetical later opportunity to talk to her.
I guess I'm basically asking if DMing her would be seen as creepy, and as well how possibly damaging that would be for my reputation in her eyes. Also I don't even really know what I'd say to her, as I don't have reason to contact her other than the fact that I like her. Any feedback into this would mean the world to me, so I can get some perspective instead of going back and forward about this in my own head.
submitted by /u/Letusgettropical
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