For the record counting only gives you a relatively small edge over the house, a couple percent. And the way you actually make use of it is by betting less in unfavorable counts and betting more in favorable counts.
I really don't think he will, it'll be a bit too much of an escalation if he does. It'll be hard for future fights to really feel like they have stakes narratively if he wins here
It'd have been really funny if he had fallen for her friend, only for her to actually be lesbian. Just to add another notch in his failed to start crushes