The series begins with Becca on the eve of her second wedding. It all seems perfect this time around, but she is still plagued by doubt. What if she could fix everything, and make the 'right' choices this time? Becca finds herself thinking about her former best friend Lolly, with whom she had a falling out many years ago. If only she could talk to her once again... Suddenly, after a freakish elevator ride, Becca gets the opportunity to do just that as she wakes up in New York City on the morning of her first wedding day in 1995. She's about to marry Sean, a bad-boy artist who is all wrong for her - and she knows her first move must be to reconnect with Lolly to re-live that day. Can she 'make it right' by living her life all over while readapting to life in New York City in the 90's - a time of smoking in bars, carrying pagers, having an AOL.

It's the fallout from Becca calling off her wedding to Sean. Her parents are angry, Sean is heartbroken, and her new self-appointed position as VP of Simon's company isn't all it was cracked up to be.

Becca is reeling from her kiss with Andy. Meanwhile, Lolly is actively avoiding Jamie. It's Nervous Lois' birthday and the girls are going out! Only problem is... Melanie is going with them. Phoebe's decision to break her plans and go out with the girls could drastically change her future.

Lolly breaks her tradition with Becca and decides to go to Grumpy Rick's annual Halloween party with Jamie. The party gives Becca a chance to make a play for Andy. Sean's back in town from the honeymoon and it appears he's moved on to someone new.

Becca is given her first work assignment from Chester and Victoria, which leads to a road trip with Lolly and Paige to Chapel Hill. Jamie wants to make things right between Andy and Sean. Lolly runs into an old friend who could be something more. And a decision that Becca makes has dire consequences.

Everyone clings to hope that Andy is going through after his car accident. Paige and Sean grow closer and connect over being artists. Jamie's bold gesture to win over Lolly backfires.

A Very Brady Thanksgiving is held. Meanwhile, Becca and Sean make adjustments as a couple; Lincoln learns about Jamie's academic probation; and Andy poses a game-changing question to Melanie.

Paige invites Sean to work with her at an art gallery, where he encounters the intriguing Noelle. Meanwhile, Lolly battles through nerves to tell Kevin how she feels about him, and Becca reflects on her past with Kevin.

Lolly is on a mission to get over Kevin by throwing an XXXmas party. The release of Thermal is a success, and Becca is walking on sunshine until Kevin does something that may force history to repeat itself.

A shocked Lolly witnesses Becca sharing a kiss with Kevin. Meanwhile, Sean showcases his work at an art show and hopes Paige will be his date, and Becca and Lolly experience a pivotal moment at a New Year's Eve bash.