“Be better than The Gap.” Meaning, you have to invest in your image in the same way that women do. Women care about brand names and they care about shoes. So if you want to appeal to that market, you better not be wearing cheap sneakers and baggy second-hand jeans.
He demonstrates excellent frame control throughout. In the scene when he is hitting on Hannah, she says “Time to go home.” Rather than fighting her or begging her to stay, he says, “That’s awfully forward of you,” and proceeds to play as though he fully expects to go home with her. Also, when Jacob sees Cal striking out at the bar, Jacob beckons him over as though he is a king summoning a jester. Cal has no idea who he is, but comes over immediately.
He does very little work. He gets women to talk about themselves, to prove how interesting they are, while he simply listens and watches for IOIs. Then, once they’ve shown enough interest, he uses the same one-line closer: “You wanna go?” He holds all the hoops, and women are more than happy to jump through.
He teaches Cal that he is sabotaging himself by burdening women with his own insecurities, his sob story, and his lack of confidence. “Your wife left you because you lost track of who you are as man, and as a lover.” Painful, but true.