Tyler comes up with an ingenious plan to "create" the perfect woman for Milo and help him find an offline love…online. Gibbs experiences a different side of Neal while driving to a family engagement and tries to unleash the beast.

A homeless man decides to bully Milo to the point of no return. Neal is convinced that he needs to make a relationship power grab, and Amy isn't having any of it. Gibbs takes on a new, more respected position after finding an old pair of glasses. Tyler fakes a job in order to pick up a new customer.

A new editor is picked up at Full Steam Magazine, and the boys all do their best to impress. Gibbs' game gets shaky, Neal experiences a colossal confidence boost and Milo tries to get noticed. Meanwhile, Tyler tries to change up his dating style, and it doesn't go quite as well as he'd like to think.

Milo decides it is time to break it off with Molly, but he doesn't want to leave on bad terms. Tyler and Gibbs don't see eye to eye with the owner of their favorite restaurant. And Neal is asked to fire an employee, but he doesn't have the guts to do it.

Tyler decides to be adventurous and date a woman with kids. Meanwhile, Neal, Gibbs and Milo fight over an office that has just been vacated at work.

Gibbs' nephew Donald comes in town for a medical school interview, but a long night of partying throws off his plans. And Milo opts for a fashion change that really amps up his mojo.

Tyler's new girlfriend is all too familiar to Milo and Gibbs, so they do their best to hide the truth from him. Neal and Amy do their best to avoid the "anniversary curse," but they can't seem to escape their fate.

Milo and Gibbs have a date-off with a beautiful woman. Tyler and Rachel try to stick together through the hassles of a long-distance relationship. Neal and Amy suffer the consequences of allowing Tyler to use their apartment as a rendezvous location.

Tyler and Milo get into a roommate fight after Tyler oversteps his bounds. Amy's father does his best to replace Neal with a more accomplished man. Gibbs searches for a woman who caught his eye at a wedding. And a little bit of moonshine leads to another marriage, much to everyone's surprise.