Prologue

Elizabeth returns to New York City to start her life over. She's 38, recently divorced, twelve years away from her beloved New York, a city planner who has only taught city planning and has never planned a city. On her first day back ("What If?"), she meets two friends in the park – Lucas, a friend from her undergrad year (and onetime lover, long ago, who now identifies as bisexual), and Kate, her spirited new neighbor. Lucas wants her to come with him to meet some of his fellow activists, gathering signatures at a table across the park. But Kate wants her to get coffee and listen to a sexy guy playing the guitar, nearby. Kate calls her "Liz" – the two of them having decided the previous night, over wine, that Elizabeth should have a new name for her new life. Lucas, for his part, likes "Beth."

We see her go both ways – with Kate, as "Liz" and Lucas as "Beth." Her lives diverge in that moment. And we follow them both.

Liz's life:

Liz goes with Kate, listens to the sexy guitar guy, meets a handsome doctor in the Army Reserves who would like to get to know her, brushes him off, gets a phone call from a number she doesn't recognize and doesn't take the phone call. She agrees to go with Kate to Brooklyn the next night to hear the sexy guitar guy's band.

On the way there, Liz meets the soldier again on a subway – by chance, she insists, but Kate insists that "It's a Sign," and Liz finally takes his phone number. They meet a third time in the park ("A Map of New York"), and she agrees to a dinner date. After that date, she tells him that statistics suggest there's not much chance that the two of them will have a successful relationship, but he insists that "You Never Know." Later on, he hits it off with Kate and her girlfriend, Anne, and sets Lucas up with David, a doctor friend ("Ain't No Man Manhattan"), and Liz finally admits that he might have a chance. After deciding to spend the night with him ("What the F**k?"), the following morning, she confesses her fears to him but vows to take the leap with him anyway ("Here I Go").

Some weeks later, at her 39th birthday party, she tells Josh that she is pregnant, and he proposes marriage ("Surprise"). They get married ("This Day"), and Josh faces up to his impending fatherhood ("Hey, Kid"). Liz has Lucas and David babysit, which prompts the two of them to consider starting a family together, and, when Lucas wavers, David urges him to commit to their relationship ("Best Worst Mistake").

A couple of years later, Liz and Josh have a second son, and Josh is called up to serve with the Army overseas, where he is killed in action ("I Hate You"). Liz struggles to move on after his death ("You Learn to Live Without"), not wanting to confront her loss until David helps her to do so ("What Would You Do?"), and she realizes that each of us, every day, is "Always Starting Over."

Later, she meets Kate and Lucas in the park, some five years after that fateful first day, and she also reconnects with her old grad school friend, Stephen, (whose phone call she didn't take that day five years ago, and who hasn't been back in her life until now). Stephen has a job offer for her, a great one, and she accepts, ready to build something new.

Beth's Life:

Beth goes with Lucas, doesn't meet the handsome soldier and takes the phone call, which turns out to be from her grad school friend, Stephen. We learn that Lucas has been holding a torch for Elizabeth all of the time that she's been away. She deflects his advances, but does agree to go with him to a protest that his group is holding the next night in Brooklyn.

The morning after attending that protest, Beth meets Stephen at the Department of City Planning, where he offers her a job as deputy director, which she takes and soon comes to love ("A Map of New York"). She and Stephen prove to be great partners at work – but, when the chemistry spills over, they have a romantic encounter, and Beth immediately regrets the moment ("What the F**k?"), and worries that it may mean she needs to quit her job. Lucas comforts her and asks to be more than a friend to her ("You Don't Need to Love Me"), but she gently sends him on his way.

Kate and Anne, along with Beth's new protégée, Elena, convince Beth not to quit and to seize a sudden opportunity to be Director of City Planning ("No More Wasted Time"). At a small birthday gathering some weeks later, Beth confesses to these three women that she is pregnant ("Surprise") and, even before she can tell Lucas that she's with child and he is the father, he proposes marriage to her.

We next see her, not pregnant, and alone, "Walking by a Wedding" and wondering if she'll ever meet the man whom she is meant to love. Two years later, she meets Lucas in a park, and we learn that they haven't spoken since she had an abortion without first consulting him ("Some Other Me"). Later, after Elena leaves Beth's employ to move west with her husband and new baby, Beth is reunited with Stephen, who wants her to come work with him again... and possibly more. She turns him down but reflects on the on the life that she has made for herself ("You Learn to Live Without").

After a routine business trip turns terrifying when her plane makes an emergency landing, Beth calls Lucas and insists that they belong in each other's lives. She rushes home to Kate and Anne, who are facing a crisis in their marriage and considering a divorce, urging them to "Love While You Can."

Some weeks later, Beth meets her friends in the park, telling them that she has decided to run for City Council – to start over again. A handsome doctor in the Army Reserves approaches, just back from his third tour overseas, and asks her out. In this life, at this moment, she says yes ("What If? – Reprise").