That's honestly what I'm struggling to figure out right now. I have a very strong feeling that I'm going to spiral when it does happen and that's obviously not good.

But, it has been a few days since I posted this and to be honest nothing has changed, we fell right back into our normal ways without any awkwardness. I'd like to tell myself that I'm mature enough to handle it, but I just don't know.

That would have absolutely been the best approach I think. It's something I had thought of after I already messed up. I did consult one of my other friends before pulling the trigger, but a second opinion with a mutual friend would have probably saved me a lot of anguish.

Honestly, thinking it over for most of the day, I'm still not sure what the best approach would have been. I think the timing was horrible on my part and something like that should really never be done via text. However, I really didn't want to spring something like that on her in person in case she would have felt trapped or cornered. I think texting allowed her to really take a bit to interalize things and provide an honest answer without the "threat" of coercion.

That said, would I have done things differently now that I've had all day to pine over it? Absolutely. I probably shouldn't have done anything and just been content with the friendship that we've built these past couple of years. But, of course, I had to go and make things complicated because I caught feelings for her.

I really appreciate your thoughts on this, it's very helpful! You're absolutely right, the timing was terrible and I immensely regret it. My thought process was that I should make my feelings known before it's too late and she ends up choosing someone else. But, that obviously doesn't matter if she was never interested in the first place.

Before I decided to go and mess everything up, we had a great relationship and now I don't know where things will end up. I just wish I had the forethought to not say anything. The older I get, the smaller my friend group gets, so messing up a relationship with someone I truly care about has really taken a toll on me. I also am acutely aware that she's still going through shit with her recent breakup and here I am making it all about me, definitely not cool.

I do seem to find myself in situations where I fall for people that are unavailable. It's not something I try to do and it doesn't happen all the time. I really only fall for people that I have a strong connection with, but that feeling never seems to be mutual, so that's clearly an issue on my end that I need to figure out and address.

I absolutely want to continue the friendship and honestly just try to forget that any of this even happened. I spoke with her a bit more and it seems like she's willing to not let this affect things, so the ball is in my court to not fuck things up like I seemingly always do. The hardest part is trying to bury these feelings that I have, but I'm down to do whatever it takes to not lose her as a friend.

I definitely appreciate the brutal honesty in your response. I should note that it wasn't necessarily my intention to establish a friendship before anything else. We met just before covid hit and I didn't know much about her personal life at that point. I never saw any indication that she had a boyfriend already and was planning to ask her out at the next happy hour (not work related). But, covid struck before that happened and we didn't reconnect again until everything settled and that's when I found out she had a boyfriend.

As I mentioned, I was fine being friends with her while she had a boyfriend because I genuinely enjoy her company and knew that nothing else would ever come of it because she had been in this relationship for so long. The only reason I made a move at all is because I didn't want to miss my opportunity by sitting on the sidelines. The fact that the breakup is so fresh means it was obviously a bad idea to ask her out and that's all on me.

I'm really just hoping we can move past this awkwardness because at the end of the day she's still the best person in my life regardless of our relationship status. I dunno, I can't help catching feelings for someone that I connect with on such a deep level, it's not like I meant for it to happen, ya know?

I sent the text this morning after we left the gym, not sure she'd believe that one. I guess all I can do now is play it by ear and try not to botch the situation any further.

I think you're absolutely right! I can't say I really go into these relationships looking to be friends first, hoping for something else later. It just seems that circumstances usually guide the relationship into friendship and then I guess I just misread the situation and end up making a mess of things. Appreciate the insight!