My question is, what's their interaction like?
Are they hanging out all the time or just once a week/every other week?
Are they doing any type of physical play? Kissing? Touching? Oral?
Is he always paying on dates or is she breaking bread as well?
Is she doing favors for him? Cooking? Running some errands? Giving him money makers?
For the average dude, p*ssy is the end all/be all. So, if that's not happening, then no matter what, he's losing in the mind of the average dude.
BUT, even if this chick is trying to be coy, if she was breaking bread, running errands and cooking for the dude all while he lays back with other chicks on the team, then he's coming out ahead. But since it sounds like you think he's losing because he's not smashing and birds of a feather flock together, then something tells me he's paying for all the dates, running errands on her behalf and getting no type of offering/contribution. And he feels like a sucka for not smashing by now.
So, in that case, he is losing. Not because he's not smashing. But because he's getting no kind of contribution from this woman and one busted nut would make all that go away(in his mind).
Peace