Dear Dr. Romance:
My best friend is leading me on. What do I do? My best friend has been leading me on for quite a while. We flirt a lot but we still aren't dating. A month ago, we confessed that we liked each other, except he wasn't ready for a relationship. I was okay with that. But now it just seems like I'm falling into the friends with benefits category. Today he took me out for a walk. He put his arm around my shoulder and I put my arm around his waist. It was out of the ordinary.
My friends always comment on how we're practically dating. I won't ask him out because I know he will say no. A few weeks ago my friends talked to him about it and he got very upset from the matter. He seems to think that he always screws up a relationship, but doing nothing is screwing it up even more. What should I do?
This relationship sounds like it's going nowhere. Being friends with benefits will only get you farther away from a real relationship with him. Start dating other people, spend less time with him, don't be affectionate. Make it clear that you're just going to be friends, not very close, if he doesn't want to commit. Only your behavior can let him know that you're serious about wanting a real relationship. When he knows you're looking for another guy, he'll either step up or let you go. If he lets you go, he never really wanted a relationship.
"Asking for What You Want" will help you be more direct about what you want, and "Friends With Benefits" will help you understand how to make sure the relationship has a good chance if you do decide to get together. Gay Relationships: How to Find Them, How to Improve Them, How to Make Them Last offers everything you need to know about same-sex relationships.