S1·E2 The Matchmakers

There is dual girl trouble in the O'Hara household. George, the dog who Tim is looking after for Mr. Burns, is in love with Chloe, the dog from next door. Through trying to get George and Chloe together, Tim falls for Chloe's owner, Marsha Carson. However Marsha has had some recent relationship problems of her own. Howard Loomis, her boyfriend, took off to Mexico without as much as a goodbye. Because Marsha feels betrayed by Howard, she is now overprotective of Chloe and suspicious of all men, including Tim. Tim's case is not helped by Angela, who bad mouths Tim to Marsha solely because Angela has a crush on Tim herself. From information from Chloe, Martin finds out the whereabouts of Howard, who rushes back to Los Angeles based on "anonymous" information provided by Martin. Howard, whose departure to Mexico was beyond his control and who tried to contact Marsha prior to his departure, clears the air with her and reignites their relationship to the point of getting engaged. This leaves Tim out in the cold. But at least all works out for George and Chloe, as Tim is given the task of sitting for Chloe while Marsha and Howard rush off to Las Vegas to get married.