Ben begins to develop romantic feelings for Riley, but his reputation for being an irresponsible playboy works against him. Elsewhere, Tucker attempts to date a model and Bonnie uses Emma to get close to an attractive stranger.

Ben discovers a shocking secret about Riley's new beau, Fitch, and tries to warn her. Meanwhile, Bonnie accidentally sends a revealing message from Danny to Riley's cell phone. Things heat up between Danny and his new model girlfriend, Milena, and Tucker pounces on an opportunity to shine with his boss, Chase.

Bonnie sets up her new bachelorette pad across the hall, and Ben and Tucker will do whatever it takes to force her out. They throw a huge party that threatens to damage more than Bonnie's new apartment. Meanwhile, Danny seeks Riley's advice on how to break up with Milena. Instead he ends up in a compromising position, which Milena mistakes for a marriage proposal.