Hey Meredith,

Wow. I am such a mess right now. I think I’m in love with my best friend.

Let me go back a few months. We both knew each other but we didn’t really talk. Then in February we started talking. We got really close, really fast. (At least I think we did.) At this time he was dating this other girl, “Jessica.” Jessica and I were friends at the time but it wasn’t a big deal. She was never jealous of my friendship with him. And when they had couple issues, they would both separately come to me for advice. You could say I was proud of my love-helping skills.

They broke up in June and he was a mess. I was there to comfort him through it all, and I felt so bad for him. He loved her so much and she just dumped him. Throughout the summer we got so much closer. Of course, we couldn’t meet as much as we wanted to but we talked all the time and got very close.

In the past month or so, I think I started falling for him. Originally it was just a joke and I would anonymously tell him about how much “I” loved him. I started leaving places early just to see him, and walking certain ways to make sure I bumped into him. I was talking to him the other day and he told me that he wants to know who the anonymous girl is … but I don’t have the guts to tell him it was me. So I told him it was one of my friends. He told me that he thought the girl said some of the cutest things, but he doesn’t want to date anyone. He’s scared that he is going to end up hurt like last time and isn’t sure how he will be able to take it.

The problem is, I’m sure that this isn’t just a mini-crush. I am falling head over heels for him. And I really want to tell him. I just don’t know how. Ugh. This is so hard. I guess I need some advice on what to do next and whether I should tell him and how to deal with my feelings and wow — I am a mess.

Thank you so much in advance!

– I Think I Love My Best Friend, New York