Dear Meredith, 

I’m kind of at a standstill and I don’t know what to do. All of my serious crushes have been on close guy friends. One in high school, two in college, and now I’m faced with the same feelings for the same friend from high school again. 

We’ve been friends since performing in a school musical, and we drifted for a few years during college. At one point a few years later, he reached out to me, expressing how he wanted to be friends again. I was a bit hesitant, as I had the past memories of really liking him but being too nervous to tell him. 

At times in high school, he was very mean to me as well, so I think this piece helped me detach and allowed me to grow as a person apart from him. I did end up texting him that I had feelings for him before moving away for college – I felt like I needed to close a chapter of my life – and I remember him telling me that it was so sweet of me to express my emotions, and made me promise to keep in touch. Years later, I found out that he was in a relationship at that time and I didn’t even know … so awkward. 

As a side note, during college, I told a new guy friend I had feelings for him after a long built-up saga, and we stopped being friends. That crushed me and severely changed the way I’ve decided to express my feelings moving forward, which would be to never tell a guy I like him unless he tells me first. 

After reconnecting with my friend from high school a couple of years ago, we developed a closer friendship. We would go on walks every week, and after he moved out of state, we talked on the phone almost every day. He always wanted to know details about me, my friends, and my family. He remembers the small details I’ve mentioned here and there. He has a deep, smart mind, and I admire his knowledge and goals in life. We talk about a lot, but sometimes I notice he doesn’t seem like he’s healed from past relationships. He talks about those girls a lot.

I went to visit him the other weekend which was a big thing for me, especially since he’s a plane ride away and it would just be the two of us. To me, we had an amazing weekend, cooking dinner while drunk, talking about life and singing together during every car ride. He watched my favorite movie with me, and went to a church I really wanted to visit, staying with me through the whole service, even though he comes from a different background and religion. 

During the weekend, he mentioned he’s talking to a girl on a dating app, and would ask for guidance on what to say to her or how to answer her messages. Part of me thinks: a guy who might like me wouldn’t do that. But part of me still feels confused. He can be so sweet and is such a wonderful listener and is so thoughtful, but I just don’t know if there might be a part of him that likes me, and I’m too scared to go through losing another friend because of my intense feelings. 

He’s moving back home in a couple months, but will be starting a new chapter in his life that makes me wonder if we will even stay friends. I’m nervous, emotional, and really think I love him. Any advice? 

– Closer