If I go with Fem!Richie-with-no-memories, he'll totally be hitting on guys around Marina. Richie tends to look at flirting as subterfuge (for himself) or something to do for fun. With no memories, he's just go with it. Fem!Richie with memories will freak out and proceed to spend hours trying to find a way to fix it because BOOBS NOPLSXTHNX.
So either way could work, but Richie's pretty deep in denial. It would be a step on the road!