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Jenna feels upset when she sees a girl, Oliva, coming out of Matty's truck, leading her to think that when Matty said he wasn't ready, he meant with a dork like Jenna.
Matty later reveals that Olivia is actually his girlfriend-in-law. Matty is the drink-server in the knick-knacker intake gathering.
Before the beginning of the series, during summer camp he took Jenna's virginity in a supply closet, although after they had sex, he told her that they should keep their relationship a secret, which slightly angers Jenna.
Matty brings Jenna to his family-restaurant, and it is revealed that she is the first girl that he has gone on a date with and thus the two begin a short-lived relationship.