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I remember seeing this guy at college orientation and thinking he was hot and my type. I forgot about him until we started school, lived in the same dorm, and became best friends quickly. My roommate regrettably slept with him about five months ago, and toward the end of the school year, one of my best friends from home came to visit me. She told me she thought my friend was cute so I decided to set them up and they slept together.
After the year was over, I went home and really missed him so we FaceTimed all the time because he lives far away. A few weeks ago I had him and some other school friends over to my house, and my home friends as well, and he and my best friend slept together again. This last weekend I was at the beach and met up with him while he was vacationing there. I went to the beach with his family, we went cliff jumping, and his family even invited me waterskiing on their boat. All this hanging out with him and his family only made me like him more. After the first day we hung out, he texted me saying his family liked me a lot. But the next day we were walking along the beach and he told me how he met up with a girl from Tinder and how great their night was. He told me that if his parents asked about the night before, he was hanging with me and we got pizza.
How do I/should I break out of the friend zone? I am 20 years old and have never been in a long-term relationship. I'm not sure if I just love him like a brother or if I actually really like him more than a friend. It's just weird because he’s my best friend so I wouldn't want to ruin that. And the fact that he's been with my other best friend (and roommate) is slightly uncomfortable.
"I'm not sure if I just love him like a brother or if I actually really like him more than a friend."
It doesn't sound like you love him like a brother. This entire letter is about wanting him for yourself. That means this man is not your best friend. He's the guy you adore who slept with your best friend (and also your roommate).
I don't know if there's any potential here, but there's only one way to find out. You'll have to come clean to him and explain that your feelings have grown over time. You can ask him how he feels and whether he's thought about more. Then, depending on his answer, you can make some decisions. If he can't reciprocate, you might need some space from him. You’re not the person he should talk to about great Tinder dates. You're not someone who'll be able to set him up, at least not now.
Depending on what happens during the reveal, you might also want to talk to your real best friend about your feelings. It'll be awkward, but it doesn't sound like she's invested in a relationship with this guy. She only sees him when you bring him around.
No matter what happens, one of the big lessons here is to ask for what you want, and to be a little less selfless when it comes to your romantic life. If a best friend says she thinks someone you like is hot, let her know you think he's hot, too. Don't set people up if you long to be with one of them. You don’t have to be a good sport at your own expense.
Readers? Disclose the crush?