I'd start by explaining to the guy who has spent a lot of time with you, if he is going above and beyond to try to get you to like him romantically, to stop, because you do not think of him as boyfriend material. Then the guy will know where you two are and that he has no chance and therefore will either stay as your friend or not. In the future be vigilant and if a guy is becoming obviously keen for a romantic relationship and you aren't interested, tell him. In relation to who you fancy I wouldn't feel guilty over it, but i would try to reflect on why you would bother daing guys who have a "bad rep". How do you value yourself? Do you feel like you only deserve these men because you are unworthy of someone who will treat you well? If you just like bad boys because they are dangerous and exciting, then fair enough, but are you going to allow yourself to be hurt by these guys who are known to the community to be poor at relationships through infidelity and lying? Have you tried waiting for someone who has all your criteria, but will treat you well?