Dear 100 Hour Board,
I recently started crushing hard on one of my best friends (she/her), and so I fessed up to it to her (on my own). She said she’s flattered, but she doesn’t quite have that connection with me. I’m not a person to obsess over anything (at least not on the outside), but at the same time, I’m not going to move on right away. I also don’t want to “move on” because I really only get these feelings when I’m really close to someone. What should I do? Should I try to convince her to take a chance on me?
– Dazed and Dreaming
If I were in your shoes, I would probably try to take a chance and see if I could do anything to see if a romantic relationship would work, and if it would, to see if my friend wanted to be in a romantic relationship. I'm building off of my premise that if I were to be in another relationship, I probably wouldn't hang out much or it would make my partner uncomfortable if I hung out with my other friend, especially my partner and I were in a more serious relationship. If in your case, you feel that you can keep this friend despite other romantic relationships, you probably want to consider differently and tread very lightly, not trying to force anything. But, if you think that this relationship will pretty much end when you get into a serious relationship with another person, I would say go for it.
I'm sure you're already taking into account what she really wants and not forcing her into any sort of relationship, but if you can convince her to take a chance and that relationship builds over time, I think it would be great to have a romantic relationship with someone who was your best friend. With that in mind, I also don't know exactly what kind of crush this is. If it's a "hey, I just noticed that you're attractive and really cute" kind of crush, then it will probably go away over time and you don't need to worry about it, but if it's a "wow, I realized that we would make a great couple and could have a great relationship, and I really want that right now", it might not pass with time, and a relationship is more advisable, since this is a lot more like the love that needs to be kindled in long-term relationships.
Either way, I wish you the best of luck, and hope the pandemic's not just ruining everything.
As long as you respect your friend's boundaries, you should do what you think will give you the best result. Perhaps if you were to "try to convince her to take a chance", she would end up completely avoiding you. Perhaps she would come to develop feelings for you. I don't know which is more likely.
Things like this are messy, and nearly if not completely impossible to predict the outcomes. Best of luck to you.