I'd say no, When you chat up a 'better looking girl' as you put it, theres less to lose really... ? I think theres more chance with the better looking girls, as they're chatted up less often and are often less confident...
also getting rejected from a 'less good looking' girl would surely be worse?
but if I was making a play, I'd like the girl the same anyway and rejection would be the same... maybe : )
Its like having a high red and a low red on deal or no deal,
with the high red, the rewards are gonna be more, but the drop could also be bad, but its worth the risk!