He talks about his insecurities all the time, but that's never an issue. In some ways, he is a chad. Like he's not scared to strip at any time. He's comfortable with his body. And that's why Khalyla talks about when they first had sex, how Bobby stripepd suddenly and started dancing.
He really doesn't care about his appearance now though. Which in it's own way, is a Chad thing. He's comfortable being himself.
He's funny of course. He can always make her laugh.
He's spontaneous. Just being a weird random guy.
The truth is, they're in a long term relationship, and neither puts as much effort into it as they used to. Bobby especially, if what they say on the podcast is true. He spends a lot of time playing video games, ignoring her. Which is how his money became a topic. Because half-joking, the idea is that because he's being lazy in other departments of the relationship, he then needs to compensate with his money. Had he remained an attentive boyfriend, then money wouldn't be an issue. In other words, she's actually saying that time spent with Bobby is valuable to her, and she wished she had more of it.