Me and my best friend have been amazingly close for 7 years now. We’ve always been really flirty with each other and when we first met we dated for about a year. He’s who I eventually ended up losing my virginity to and the only person I’ve ever hooked up with. Recently he has been talking about how he really thinks we should date and it has been kind of awkward because I am unsure if I feel the same way. I mean, I love him but he has many habbits and small things that he does that drives me crazy. Then I remind myself that I’m never going to find someone that is identical to my dream guy. There’s always going to be those little things. We’re complete opposites though … he’s a complete flirt with everyone and (I think) pretty clingy in relationships. We’ve had conversations like this before … about dating … sometimes we’ll even joke about marriage if we’re drinking or whatever but it has always been in such a joking way that I never thought he was being serious. I’m scared if I straight up say no it’s going to be really weird because we do kiss more than often and he tends to already sleep over at least one night a week. But I feel like if I say yes it’s going to be weird because like I said we are so different with relationships and because of the whole “what if it doesn’t work out” sort of thing. Gosh, my friends would just die laughing if we started dating. He moved out of state about a year ago and is moving back this month which I guess is why he has now asked. He called me upset because some girl asked him out and he declined and apparently really hurt her feelings … he has a real hard time letting people down or being mean to people. After some prying (I’m nosey so what?) he was talking about how he was trying to comfort her saying there was nothing special about him. She went on to say really nice things about his personality and looks … and it’s weird because so many people really do like him on a romantic level and it’s weird that I am unsure if I do. I’m rambling at this point. But then I remind myself that if he had another girlfriend that wasn’t me how jealous I would be and how it would suck. That’s gotta be some sort of sign? Well anyway, thought it’d be interesting to get an outsiders perspective.