I always find something wrong with a guy...

I'm very similar. I usually don't even click with someone on a friendship level until a while after I have gotten to know the person. I believe I am this way because I am insecure, and don't open up and connect with people right away. I am very guarded and very afraid of being judged (and it isn't just a gay thing).

If I were you, I would try to stick it out a little longer in the future. But you make a good point, when do you say, "this is it, no more dates for me!" I don't really have a good answer for you because I am trying to decipher that myself. I am currently "seeing" someone. We have hung a bunch, and we have hooked up and stuff as well including several over nighters. Like you, I have found a couple of petty things I don't like about him (I guess don't like would even be strong, probably better to say things that make me thing eh he aint the one), but not enough to say "this is it." However, I sure as hell don't want to lead someone on and worse, hurt this person. So I don't know, it's tough.

 

This question has a great deal of complexity.

Analysis can be both a fault and virtue. I will assume the reasons for both are obvious. To that end, from my experience with lawyers I have detected a pattern. Lawyers, being the expert examiners they are, often strive in their career which demands thorough evaluation. This success comes at the cost of their spouse feeling unable to keep up with the intelligence, thought and depth of study.

In short: pursue what personality you wish, but maintaining scrutiny in a relationship will never help it advance. EDIT: I realize scrutiny might be a stretch from analysis, but doubt may be more accurate. I see nothing in this post that resembles trust, just doubt in their compatibility with you.

Nevertheless, there are always exceptions. Alcoholic consumption, drug abuse, promiscuity, smoking, etc. are all important considerations. To each their own and I wish you the best in your decision. Perhaps now would be a good time to exercise your talent for analysis. Is alcohol a lifestyle you promote? Can you accept it when sharing a life with someone else? There is no wrong answer; there is only honesty.

Like with most dilemmas, there is no absolute answer here, either. There is an exceptionally fine line between pickiness and indifference. The former is obnoxious, the latter is unfortunate.

I'll try to keep this next statement as brief as possible to conclude my answer. There will always be annoying traits and behavior in someone (leaving a mess in the kitchen, not the perfect teeth, an undesirable characteristic or family, etc.) and unless it is a dependent factor that changes your relationship in a fashion you dislike you should keep trying. The "dependent" factor changes from person-to-person, too. Family is generally an independent factor, just as careers and hobbies are. Dependent factors are things which require another individual to complete: children, a house together, shared finances, caretaker for kids, etc.