well she says he wont' be able to get over his issues about not dating enough without experiencing dating on his own terms --ie he has some fantasy idea in his head and getting out there and seeing reality will break that. And she also says that it will make me appear more desireable because a lot of men will get jealous when they see their SO dating someone new.
Also at this stage I'm really hesitant to switch MC, because H is so ready to bolt.