Analeigh Tipton

Jessica is Robbie's babysitter and crush in the romantic comedy Crazy Stupid Love


Jessica is a naïve 17-year-old who believes that girls shouldn't date boys if they're younger, but sees no problem chasing men old enough to be her father. Despite her hypocrisy, she's a well-meaning girl who has yet to fully understand how romance really works.


Robbie WeaverEdit

Robbie has had a crush on Jessica since she started babysitting him. He clumsily tries to woo her, but is constantly met with rejection as Jessica feels he's too young for her (he's 13 and she's 17). Each rejection is only met with an even more contrived declaration and finally Jessica snaps at Robbie after he publicly embarrassed her in front of their entire school. When Robbie finds out that Jessica has a crush on his dad, his spirit finally cracks. At his end-of-year speech, Robbie uses the opportunity to tell everyone how overrated love is. Seeing how badly he had taken this, Jessica feels sorry for Robbie and decides to give him a consolation prize: the photos she originally wanted to give to Cal.

Cal WeaverEdit

Cal is Robbie's father. After his wife tells Cal she wants a divorce - in front of Jessica - she admits to having a crush on Cal, but he refuses to hear it. Jessica then goes about trying to get Cal's attention in the same way Robbie tries to get hers. She takes several seductive pictures of herself and puts them in an envelope with Cal's name on it. Her parents find this and assume Cal was taking advantage of her. Upon seeing how she'd nearly got Cal sent to prison because of her crush, Jessica decides to give up on him.