Bob tends to be very protective over his daughter, especially when it comes to her dating. He has a habit of scaring away any boy she is interested in. When he shows up unexpected the day before Cece's Wedding, he is stuck spending the day with Nick, who had just slept with Jess. Nick at first doesn't want to touch the subjuct of dating, however finds a way to talk about his feelings for Jess referring to her as Yolonda Winston. He reveals to Bob that Yolanda is actually Jess, to which Bob reacts by chasing him and screaming "I'm going to kill you!" He feels that Nick is alot like himself, and the reason why he doesn't accept Nick is that he 'isn't good enough for his daughter.