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.
Becca, as she nears 40, is about to embark on her second wedding to Andy Kelly, but her joy is tempered by the absence of her old best friend Lolly who's a no-show, having dropped out of their relationship years ago. As Becca mulls over her past with Lolly and the mishap of her marriage to her first husband, Sean, she wakes up on her wedding day and discovers that it's 15 years in the past - she's about to marry Sean, her own parents are still married, and Lolly is still in her life. Becca must now decide to either go ahead with her marriage to Sean and watch the years play out as they have before, or chuck it all and try for a re-do of the history of her life that's still in the future.