New to NYC, Dana encounters purses she wants to buy, co-workers refusing to work with her and a bad blind date. Peter's attitude makes a poor first impression, but given a second chance, they might find something to like about each other.

After seeing Peter on a date with another girl, Dana tries online dating to prove she's not a monogamous kind of girl, which she totally is. Peter's jealousy leads to more awkward run-ins and the pair just might relent to one more date.

Dana and Peter seem to have reached the perfect relationship balance--they've jointly agreed to see other people but not talk about it. But their dating anonymity is all about to change when Dana learns of a long-standing dinner party Amy is hosting at the loft--and the fact Peter is attending and bringing someone else as his date.

Dana and Peter continue to enjoy New York and each other, but when they realize they still haven't had sex, both decide tonight's the night following a sexy and swanky dinner at an upscale oyster restaurant. But when the couple finds their reservation is pushed, Dana and Peter head elsewhere, not knowing that their romantic evening is about to go from intimate dinner to disaster. Meanwhile, Amy and David spend an evening babysitting and make a decision that will impact their future forever.

One thing is for certain when it comes to Dana and Peter's relationship, the road to love is paved with quite a few ridiculous fights. The topic of their latest disagreement is none other than the holiday-themed romantic comedy, Love Actually, and it could not come at a more inopportune moment.

An impending storm is a fitting end to a tough week for Dana until her boss calls with her first book to edit with a quick deadline. But when everyone she knows shows up at the office to wait out the storm, Dana is annoyed by the distraction until the power goes out.

Dana is forced to reveal an embarrassing hobby (LARPing aka Live Action Role Play) to Peter when he joins her on what he believes is an out of town work conference. But a supportive Peter eventually misses Dana and decides to join her on the playing field putting everything she's worked so hard for and loves about the game in jeopardy.

When Dana replaces Peter with Tucker as her plus one to an old friend's wedding, Peter quickly realizes that he'd rather have a miserable time with Dana than a wonderful time without her. Amy skips her spin class to secretly take dance lessons in preparation for the wedding and David thinks she might be having an affair.

Peter is embarrassed by his family and doesn't invite Dana to Thanksgiving until he knows she has plans to go home and can't make it. But when Dana's flight home suddenly gets cancelled, she ends up in the middle of Peter's horrible family Thanksmas tradition and is determined to turn things around and have fun.

When Peter learns that Dana is still friends with all of her exes, even the one who proposed, he takes her cue and tries to reconnect with his one long term girlfriend. Plus, there is conflict at Cooper and Sons when Amy fills in for the receptionist and tries to tell everyone how to do their job.

In the season finale, when Dana's ex-boyfriend shows up in New York to win her back, Peter does everything he can to show Dana how much he cares, even letting her go if that's what it takes. David helps Chloe get out of her dating slump by showing her how to use the Cooper family secret dating trophy.