How about being a mobster/gangster? I think that would definetly help or increase your chances. Some (not all, ok maybe most) are looking for a sugar daddy or someone willing to show them a friggen expensive time.
Becareful what you wish for:
I don't know if this counts, I asked out a stripper from WAGG a couple of years back. I was so drunk and high one night, and by buddies kept egging me on, cause I had a hard one for one of these strippers. So finally after a had a couple of dances with her, I asked her in my drunken stupper. She took it and said I was sweet and she said if she wasnt busy, maybe. I didnt think she was gonna call, The next day I get a call on my cell with a blocked #. I really didnt think much of it, I answered and it was her!!! Holy smackers!!! We went to play pool and had some something to eat. She was actually pretty cool. Then I call her again and she told me that she had quit the business casue outside parties found out she was a stripper, and that she needs some time to herself. Cool, she not my GF, and plus I had one at the time.
2 weeks later I am walking in Yorkdale with my GF and God must of been angry with me, cause BOOM, I see this very attractive chick coming over from the corner of my eye. At first I didnt recogonize her then when she came closer, she said Hi! She introduced herself to my GF as one of my friends friends (THANK GOD!), and we chatted for a bit. I swear I thought I was gonna shit my pants!! You know that feeling of eating something that doesnt agree with you? That the feeling I got for the whole day.