Bobby is a smiley, humorous and easy-going guy who manages to smile at all of Caroline and Max's antics. He is traditional and like Caroline, he thinks the 10th date is then the date you get it on and not the 3rd. Bobby is honest and seem to truly love Caroline, putting up with the mess Caroline makes putting him in a difficult situation with his mother all the time and ruining his prospects in his hobby, bowling. He never gets mad at her, just when you think things are going down, Bobby says the sweetest thing to Caroline and they share a passionate kiss again!
Unlike Andy, Bobby is more cautious with what he tells Caroline, waiting before he told her about his Bowling hobby, knowing she wouldn't like it. Bobby knows Caroline very well and said she won't have to come to watch him bowl again before she could say anything. That was exactly what she wanted though she acted the opposite all those time.
Also, Bobby is very serious about Caroline very quickly. Introducing her to his family members. Bobby's family, mother and 2 sisters, is obsessed and still cannot get over Bobby's ex girlfriend, Jessica, mentioning her name all the time, making Caroline uncomfortable.
Despite being a jealous person, Bobby lied to Caroline, saying he wasn't jealous 'just to seem cool' in front of Caroline. But when Caroline was at the movie premiere with Andy, Bobby went to the diner and asked the diner people how was Andy like, "Is he good looking? Rich? Does he have Amazon Prime? I'm dying here." While he was there Sophie came and showed him photo of Caroline and Andy at the Premiere. Bobby asked, "Is that hand on her lower back of upper butt?" Next thing we know, Bobby appears at the premiere and shouted, "EY! Mr Candy Guy! Get your hands off my girl!" He pushed the 'wrong Andy', the actor acting as Andy.
At the very end of Season 6, Bobby meets Randy (who just proposed to Max) for the first time. They recognised each other quickly. Randy was the lawyer on set of "Move Out, You're Forty" who fired Bobby's mother and sisters from the show. They got outside and fought.