I think this is a question most girls could benefit from knowing the answer. So long story short, there's this guy I've been friends with since fifth grade and had a growing crush on since eighth. Anyways he's the perfect description of a stereotypical player, handsome, flirty, talking with a different girl everyday, leading them all on, ex.. Anyways he's given me the whole "you're different than the others, I really like you spiel" but I'm not easy to believe (Especially because usually that conversation ends with something along the lines with "we should hook up") I don't want to be another notch in his belt so I've never done anything with him. Anyways I know at one point he actually did like me, but this was back in my socially awkward middle school days and I didn't know how to deal with guys having crushes on me (it was right when I hit puberty and while before I was an ignored by every guy in sight and practically overnight guys started paying attention to me) anyways I spent that year awkwardly stay away from and ignoring any guy that liked me so nothing became of it then. Anyways I really like him but don't want to be kidding myself thinking I won't just be another chick he gets, so if anyone has any suggestions helpful to my predicament in specific or any generic tips for girls who have struggled with this question it would be great to hear a them! :)
Most Helpful Girl
since he's your friend, I suggest that instead of making a move on him, or trying to decipher if he has "genuine" feelings for you, you could simply start by discussing relationships with him. If he's a known player, confront him about this, not in a mean "I disapprove what you do" way but try to know if he sees himself in a long, committed, stable and genuine relationship at one point. You could ask him why he does that, and if he doesn't get tired of it sometimes (and by the same way you could try to make him see how a stable and genuine relationship is much more rewarding than what he does).
That way, you will know if he, at least, has ever thought, about being with one girl he would love genuinely
Now I know this doesn't answer your question. But, from my point of view, there really is no way to tell whether someone has genuine feelings for you or not, and this regardless of whether they're a "player". You can only know this by being in a relationship with them and as time passes by. Which is why getting in a relationship is scary and makes one up for hurt. I could be wrong but from the way you asked your question, I had the feeling that because he did like you at some point, you believe he may still have genuine feelings for you. And this is perfectly understandable, yet the only way to be sure of it is to take some risk and thus take the risk to be wrong and disappointed.
But either way, I am not that much a fan of a direct approach, I think it is better to know where people stand regarding relationship firsthand.