Jessie: Season 3, Episode 4

3 - 4: The Blind Date, The Cheapskate, & The Primate

Jessie has the kids and bertrum avoiding Tony like the plaque. One day, she exits the elevator only to find out Tony is picking up something behind the desk. The two awkwardly talk until they decide to hook each other up with friends, Tony is believed to think the person Jessie is going to hook him up with is actually her, so he fails to find someone until the last minute and he turns out to be a cheapskate, eating leftovers out of the trash.