How many dates is enough to know if a relationship is worth pursuing?
How many dates do you think is enough to know if something is worth pursuing? I went on two dates with this guy. He's perfectly nice, smart and attractive, but we seem to have little in common. He seems interested, but we don't have much to talk about. If we do break if off, I'd like to remain friends. Thoughts?
More Dates Needed?
Two dates is typically what I would suggest to see if there's any kind of a spark. You've given the potential relationship that much already, and the sparks aren't flying. Still, I commend you for not just giving up on someone who seems interesting, even if he's not actually catching your interest so far.
For your third date, try to steer him toward an activity or experience. Go to a play or a movie. Play mini golf or go bowling. Check out the Magic Gardens or the Museum Without Walls. You'll have something to do and something to talk about. Even if you don't have much in common, spending an afternoon looking at art together or seeing the city in a new way can give you a shared set of experiences from which to explore your outlook on the world rather than just your divergent hobbies or backgrounds.
After you try this kind of a date, reassess and see if there ought to be a fourth date. If you still feel lukewarm and unenthralled, don't feel obligated to keep trying to make it work. While having someone around who's interested in you can be a real self-esteem boost, if you don't reciprocate, you can only get so far on being flattered. It's also not fair to him, if he is actually interested, to keep going out just because he seems interested in you. (For all you know, he might be thinking the same thing.)
I'm not sure about the friendship thing, though. When someone says, "This guy is super interesting and I love talking to him, but I'm not attracted to him," that's when it makes sense to stay friends. Based on what you've shared, you sound like you're missing the friendship piece from the get-go, so I would advise letting him down gently and politely. If it's true, you can even say you have a friend or two who might have more in common with him. (I got flak for suggesting this in the past, but I can't help it! I think people should view the end of very short, very uncommitted relationships as a chance to set up their friends!)
Finally, since you're inclined to give him this third chance, go ahead and pick an activity that you're excited about. At least you'll be doing something you enjoy, and maybe by the end of the night, you'll realize he enjoyed it, too. That could be a nice starting point.