<human>: Can you succinctly summarize the text in 1-3 sentences?

The catch is that this girl is not someone who you would expect not to have a boyfriend. She is highly social, has lots of friends, and has had at least 5 different sexual partners (however not a slut, this is common of girls in sororities). She drinks a lot, and a couple of times she was drinking she has mentioned to me, while crying, that she is insecure about never having a boyfriend. However when she is sober she always tells everybody that she is glad she has never had one, although it is obvious that she is insecure about this fact. I have confronted her best friend about this, and she told me that her number 1 insecurity is never having a relationship with anyone. 

This girl is a social monster, who is definitely hot, so it is really surprising to me that she has not had a relationship before even though she clearly wants one. Another surprising fact is that she is in the bitchiest sorority in my university, so that makes it even more odd cause there is a lot of social pressure for her to have one. 

She is kind of a tomboy who gets along with guys better than girls, so this might be a factor. But I really like her, and I just don't know how to go about courting her. I am pretty sure she has shown interest, but I am kind of a pussy and am very confused.
<bot>: A girl that normally would have no trouble getting a boyfriend, has never had one (even though she has had multiple sexual partners), and is insecure about it. I really like her and don't know how to go about it.