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.
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.
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.
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.
Neal is going to propose to Amy, but first he has to get her father’s blessing – and it’s not going to be easy. Milo joins Gibbs on his yearly "samurai cleanse." Tyler finds his first gray hair and is convinced that the end is close… or at least closer.
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.
Myron, the new boss at Full Steam, has promised to fire one employee by the end of the day. When Neal shows up to work drunk, the guys rally to sober him up and save his job.
Milo’s jealousy is tested when he dates a girl who has a "same-sex ex." Gibbs gets carried away with a "fake" marriage. Tyler tries to win Myron over with Neal’s help.
Milo meets a book publisher, but it's not his writing she's interested in. Neal hires an intern and Myron enlists Tyler and Gibbs to make him look cool on social media.
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.
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.
Jude warns Gibbs that dating a girl from the suburbs is more dangerous than it seems. Tyler and Milo's friendship is tested when Tyler offers to cover Milo’s share of the rent.
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.
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 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.
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.
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.