Tyler attempts to ask Jude out on a date, but her past gets in the way. Worried that Gibbs is bottling up his emotions, Milo tries to get him to cry. The big source of Neal’s sexual anxiety is revealed.

Determined to get over Lisa once and for all, Milo revives an intense competition that once almost destroyed the guys' friendship. But he is soon forced to make a big decision when Lisa comes back into his life. And Neal struggles to prove that he's on a par with the rest of the guys.

Tyler and Jude try to keep their new relationship a secret. Milo, already feeling left out since quitting Full Steam, has his traditional movie night taken away from him. Gibbs is hurt when Neal finds a new apartment. PJ tells a paranoid Myron to expect big changes in the office.

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.

The guys follow a girl to a party to help Neal make a connection, but they get more than they bargained for when they learn that Molly isn't the host of the party – it's what's in the punch.

Milo stays with Tyler while some work is being done in his apartment, but Tyler’s only rule of the house proves a little too difficult to follow. Meanwhile, the guys jump to conclusions when they find a suspicious photo of Amy with another man.

Gibbs and Tyler test a lie-detector application, only to have their own hard truths revealed. Elsewhere, Amy and Neal dabble in role-playing games; and Milo's ideal woman turns out to be a bit too eccentric.

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.

Gibbs and Tyler pretend to be a couple in order to get a discounted gym membership, however things get uncomfortable when Tyler takes their "bromance" too far. Meanwhile, Neal sets up Milo with an old friend, but when the relationship starts to get serious, Neal intervenes.

Gibbs, Neal and Tyler band together to help recently dumped Milo get back in the game. Neal attempts "dirty talk" at the whim of his steady girlfriend, Amy. And Gibbs crosses the line with Tyler's maid.

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.

When Milo quits his job, Myron hires Jude, a pretty female writer, to replace him. Tyler tries to earn Jude's respect. Gibbs thinks his apartment is haunted while Neal has some apartment issues of his own. Milo struggles to prove himself as a real writer.

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 reluctantly falls into puppy love. Milo gets caught up in a relationship that is moving too fast for everyone to handle. And Neal teaches Tyler a lesson about the perfect hamburger.

Gibbs helps Neal plan the perfect proposal. When Neal doesn't get the answer he expected from Amy, Milo thinks it's all his fault. The guys accuse Tyler of "straight baiting" his new friend, who happens to be one of the richest men in the world.

Tyler finally lands a photo shoot featuring his childhood idol, but when Gibbs starts to get buddy-buddy with Tyler's icon, things don't go according to plan. Meanwhile, Neal serves as Milo's guinea pig for an invention that goes terribly awry.

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.

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.