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 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.

In search of adventure, Tyler and Milo accidentally crash a wake. Gibbs is surprised to find himself attracted to Neal's gamer friends, but he quickly learns the rules of Drogar the hard way when he gets too close to the wrong character.

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 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.

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.

The guys give Milo follow-up advice as he attempts to play it cool after his first post break-up date, but Milo overreacts when a "textastrophe" ensues. Gibbs and Tyler are surprised when an interview with a sex therapist is not quite what they expected. And Neal endures relentless teasing from the guys for wearing a nerdy paperboy hat that Amy loves.

Things become awkward between Milo and Gibbs after they partake in a "devil's threesome" with a woman they meet in a bar. Amy helps Tyler get in touch with his feminine side. And Neal becomes jealous when Amy and Tyler start spending too much time together.

The guys are put on edge when Neal starts cutting costs in the office to prove to the boss that he is "all man." Milo winds up in jail after attempting to get firsthand inspiration for an article about drug trafficking. And Tyler ends up in hot water when he runs into an ex girlfriend.

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.