'We're hurting, but we don't know how to end it'

I wanted to make my relationship last for at least a year, because the earlier relationships I had didn't ever go beyond six to eight months. The thing is, I know this isn't going to work out because my girlfriend and I have almost nothing in common. She knows it's not working either but she isn't saying anything, and I am continuing with it only to prove to myself that I can stay in a relationship for more than a few months. It's hurting us both though. What should I do? To end it is to disappoint myself but to continue is torture. My friends think I don't give any relationship a chance, which is why I think I should stick to it.
Your life sounds like a bad reality show. You aren't winning a prize at the end of a year, and there is no rule that says a relationship ought to last for a specific period of time for it to be deemed a success. If this isn't working, you are harming two people. More importantly, you are preventing yourself from finding someone who you may genuinely want to be with for much longer. Your friends aren't in the relationship and, though they may have a point about giving it a chance, you and your girlfriend are the only ones qualified to take that call. If it's not working, grow up and tell your girlfriend how you feel.

When is it okay for me to tell someone how I feel? We have been on dates for four months but I don't know when the right time is. I know she has feelings for me too, because she has given me a lot of hints, but I don't want to rush it and ruin the possibility of this working out because I care about her a lot.
I suggest you call her at once and tell her right now. There is no perfect time and you won't know how she feels until you ask.

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