Ben finds the cell phone of a cute girl, Sydney, but when he's unintentionally late for their first meeting, he convinces Tucker to go in his place and take the blame. But when Sydney takes a liking to the real Tucker and asks him out, Ben is determined to prove she's interested in the wrong guy. Riley meets up with an old frenemy, Heather, and enlists Danny in her plan to prove to Heather once and for all that she's a winner. Meanwhile, Bonnie asks for Tucker's help in coming up with a catchy new slogan for her realty business, but things quickly go awry when she starts getting offers from guys interested in buying more than a home.

Ben tries to score a second date with Heather in order to win a wager with Riley. Elsewhere, Bonnie asks Danny to end her relationship with Brad for her, and then she becomes interested in Brad's dad; and Tucker uses Emma to improve his dating life.

Tucker pretends to be a lawyer in order to please his dad, and Ben helps with the charade. Meanwhile, Riley develops a crush on a British guy, but Bonnie mistakenly thinks she's fallen for Danny; and the gang's trip to a Renaissance faire goes badly.