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.

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.

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 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.

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.