Tyler the Pioneer – Tyler decides to be adventurous and date a woman with kids (guest star Bethany Joy Lenz). Meanwhile, Neal, Gibbs and Milo fight over an office that has just been vacated at work. Jason Lee and Ben McKenzie also guest star.

The Good, The Bad & The Milo – 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.

Downshift – 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.

The New Boss – 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.

Will Work for Milo – A homeless man bullies Milo. Elsewhere, Neal tries to make a change to a relationship; Gibbs finds a pair of old glasses and takes on a respectable persona; and Tyler fakes a job in order to lure a new customer.

Missed Connections – 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. Sarah Wright guest stars.

Inventing Milo – 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.

Super Milo – 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.

Wake and Bake – 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.

Plan B – 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.