When Vanessa brings home her first boyfriend, Reggie, Bernie gets to work on scaring the guy off but quickly realizes that Reggie is a good influence on Jordan and could lead him away from bug collecting and into sports and girls. Bernie decides he can take advantage of the situation and let Vanessa think she has a boyfriend while also giving Jordan a role model. When this prevents Vanessa and Reggie from spending any alone-time together, Vanessa decides to break up until Bernie uses reverse psychology on her to get them back together. Meanwhile, Wanda decides to clear space in her closet and give some shoes to the Salvation Army, but letting go is harder than she thought it would be.

Bernie is thankful that Vanessa is doing well in school due to the support of her teacher, Mr. Diggs. But when Mr. Diggs' influence turns her into a vegetarian, a jealous Bernie puts his foot down. Meanwhile, Jordan makes Bryana dread her first year sitting at the kids' table at Thanksgiving.

Bernie gives Vanessa driving lessons, but he goes overboard while teaching Vanessa. Out of nowhere, he gets his truck towed away and he also gets glasses.