Cherry is not that bad, she is just... too vanilla compared to all the other options. I actually think she fits Ian the most. Lena is too... adventurous for him. And hey, at least Ian has the option to go for someone who doesn't look like they going to pull some shit any time soon. And he is most likely getting another one soon with gothy.
Lena has the option of an old rich pig, a dumbass who will cheat on her the first chance he gets, nice guy (tm), a guy with girlfriend (or is it wife?), a black guy with a giant cock who will cheat on her the first chance he gets and a guy that already cheated on her before. In other words, she has to lezz out (as Ivy would say) if she wants to get it on with someone decent. Which I have no problem with, just pointing out the obvious disparity.