Milo must find comfort in his friends after starting his day with his girlfriend breaking up with him. With friends like Gibbs, Tyler and Neil, Milo is forced to skip the mourning period and jump right back into the game.

Neal employs cost-cutting measures at work to impress his boss. Elsewhere, Milo ends up behind bars when investigating drug trafficking for an article; and Tyler happens upon an ex-flame.

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.

Testing a lie-detector app for a new article reveals some tough truths for Gibbs and Tyler. Amy and Neal experiment with role-playing, but things turn out to be very one-sided. And Milo's perfect girl turns out to be a bit kooky.

Gibbs and Tyler pose as a couple to score a gym-membership discount, but Tyler takes the faux romance too far. Meanwhile, Neal plays matchmaker for Milo and a longtime gal pal, but the love connection backfires.

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.

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.

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.