Jude has his fair share of girlfriends. Even though he might not seem interested with his dull facial expression, he would announce to his friends if he finds a girl attractive. The longest relationship he had in the series would mostly likely be Starr a.k.a, the "Freaky Vegan Chick."They got along very well although their first kiss ended in disaster when Jude accidentally threw up in her mouth due to a bad stomach. She forgave him and gave him another chance. In Jude's case, anyone who does that is a keeper. Their relationship ended when Starr turned goth and changed her name to Nebula. Jude couldn't just let her go and decided to be goth himself. Things didn't work out very well because she felt that it wasn't fair to him and they just decided to be friends.
With any potential girlfriends, Jude stays loyal to them and can be very romantic. It's hard for him to let go and he was even attached to a chair at one time. It was the "Touche-Control 3000" that he dubbed, Betty. His friends became concerned because he wouldn't leave the store. Jude says that Betty was easy going, listens to him and who can resist great massages? Even his friends couldn't argue with that logic.