I have been friends with this guy since my freshman year of college (2017). During the first two years of our friendship, I thought I was obvious about my crush on him. But we only ever hung out in group scenarios, and he does have trouble picking up on social cues. 

And when I say he is oblivious, I truly mean he does not pick up on romantic cues from anyone, even when other people flirt with him. Then COVID happened and we were hanging out online with other friends. The more I hung out with him, the more my crush would grow. 

In 2021/22, something shifted in our friendship and we became closer friends, hanging out one-on-one when we were in the same state. Our friends, aware of my on-and-off again crush on him, would point out that we gravitate toward each other in group scenarios. 

In 2022, I was leaving to grad school in and thinking I would stay there after. I wanted to get the crush off my chest and, as a cop-out, only said that I liked him when we were 19/20. He was kind of shocked and asked why I didn’t say it then, but then didn’t respond. We had a heartfelt goodbye before our separate bus rides back home.

Now I’m back from grad school, he is in another state still, and we are 25. We just spent Memorial Day weekend together with our other friends, where once again we spent most of our time together, and even hung out separately from the group after vacation. I felt the feelings coming back. Now we are closer friends, coming on six years, able to tell each other anything but also sit in silence … and I don’t know what to do with these emotions.

Is it too late to actually be upfront with my feelings and ask him out, especially if that might mean losing a friend I connect so well with – or do I give up and settle for a not-as-strong connection with someone else? I also think he wouldn’t attempt to go out with someone who doesn’t live nearby, given a conversation the two of us had. 

– truly delusional me