How to not ruin our friendship or his dating confidence?

I had a huge crush on my guy best friend for about a year and a half. We've grown a lot closer, and I started to debate if I really actually would want to go out with him, and now I've decided that I can't see us having a good relationship. But now, he's into me and is planning to ask me out soon (but doesn't know how his parents will react. They're strict, but he's 17!)

I don't think I would have any problem saying no (nicely, obviously) except for the fact that he's told me he doesn't have a lot of confidence with girls. When we went to prom, I told him that I had a lot of fun with him. He told me that was a good thing, because he did a good job, and that if he hadn't "done a good job" that he wouldn't have gone to another dance because it would have ruined his confidence. I'm worried that if he asks me out and I say no, that our current friendship will be a lot different, and that I'll ruin his confidence with asking girls out (I would be the first girl he's asked out).

We would be a cute couple. We get along really well, and everyone already thinks we're dating. I have a very different idea of relationships that he does, though. I'm totally cool with having a guy over to my house, one on one, or going out to eat or walking around festivals or the park and having it be completely platonic. For him, these would be dates. I want to be able to continue doing these things with him, but I know it isn't fair to expect him to do them without feeling like it will lead to more. But now there are reasons that I don't want a relationship. He's turning out to be very similar to my ex in the negative aspects, and he's becoming kind of clingy. He got very upset with me for not spending the entire school day with him, because we didn't have anything in our classes and normally I would spend at least a little time with him. Not only that, but we have very different takes on swearing, tattoos, money and adventurism.

Sorry about the length, but thank you!!!


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What Guys Said 1

  • For the Pete sake don't if you want to stay friends it isn't worth the risk first-hand experience


What Girls Said 1

  • you have to talk some middle ground.