I honestly think he only cares about whether he looks bad and being laughed at. A few times, Sally, when she's super pissed, told him, "dont make me embarrass you." His proposal to all these girls after a day definitely doesn't show he understands relationships or how preposterous he comes off. Still, to him, it's the ultimate flex: he's the man in his mind, and all the past shit he got dunked on doesn't matter anymore. I am staunchly against anymore troll GF arcs moving forward. He uses it to deflect from all the times he got played. Look at how quickly he buried the embarrassment of falling for the court arc. Because these "gfs" came around, he found it the perfect way to save face. When this rug pull happens, the only way it will affect him for a while is if no one else baits him for a relationship. The faster hes gets a new girl, the better for him (in his retarded mind).