Hello! I've never really done this before, but I feel uncomfortable talking to my friends about this so here it goes. There's this guy. I've never really been able to say that before. I've always kept to myself, at least romantically. Most people respected that and didn't try to connect with me that way. This guy did. He broke through the wall I had created. He asked me out three times. I rejected him 3 times.
It's not that I don't like him, he's funny I guess and really sweet. We're in the same french class and text almost every day. He gets me to talk about deep personal stuff that I usually don't talk about. We would make a great couple. His best friend is dating one of my friends. We could go on double dates and stuff. I've always wanted a boyfriend or girlfriend or something, but I've been too nervous to ask. I don't know why I always say no.
He's a bit odd and unpopular and about half the school thinks he's gay. A few of my closer friends don't like him too much, but those really aren't the reasons. I used to think it's because I have feelings for other people, but they are such nonsense crushes. One is on a girl who is dating someone else, one is on a guy who's a total jerk and I would probably reject him even if he asked me, and the last one is on a girl who doesn't like girls.
Anyway, I don't quite know my reasoning, but I don't want to be with him. I just feel bad because I don't want to keep hurting him over and over again. I've made my feelings clear to him, but he won't give it up.
Do not worry about repeatedly hurting his feelings if he is not taking the hint. Of course be respectful and courteous in saying no. Also you could be leading him on and confusing him with these deep conversations you are having. Sending him the wrong signals. You need to make it clear you just want to be friends and that is all, so to not ask you out on anymore dates.
It is also not nice to continually accept someone's affections only because it makes you feel good. Meaning you know he likes you, so even though you don't like him continue having deep talks and kind of flirting and sending mix signals because it feels good to have someone fawn over you. It is a very easy trap to set for yourself when you are young. Be kind to others feelings.
If you really care about him as a person and a friend make the boundary very clear. remember you might find yourself in his shoes someday.