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A NYC bar, early evening. Tricia, sits alone angrily scrolling through her phone and analyzing the growing evidence of her boyfriend’s most recent affair. Just Like That. Tricia is joined by her close friend Eve, a sympathetic ear with a seemingly never arriving engagement from her boyfriend Brant. Eve informs Tricia of her having invited along their friend Anne, which sends Tricia further into her funk. Anne arrives and attempts to aid Eve in consoling Tricia. As Anne gets a round of drinks, Leif introduces himself to Eve and Tricia, albeit wondering where Anne had gone. The girls hatch a plan, with Anne as bait, for her to break someone’s heart and get a marriage proposal that evening. Leif introduces himself, leaves a card, and lets them know he’ll be back with his buddies. Leif regroups with the guys and further elaborates on the lessons he’s trying to impart - Never Too Old. The guys, led by old school dating lothario Leif, are presented with the challenge of bringing home a girl for the evening. While the sweetly naïve Martin scribbles notes on how to achieve this seemingly impossible task, the cooler Chad humors Leif and joins in the challenge. Anne handles the simultaneous flirtations of Leif, Chad, and Martin while she laments on this very familiar song and dance A Thousand Times Before. Martin, having been lectured at pulling out his Mom’s wedding ring, admits feeling lost. Please Say Yes. Meanwhile, Eve sits with Chad and their casual banter dissolves into confessions of how their most recent relationships have failed. Eve sees everything her boyfriend is not in Chad and the two tip toe into a casual flirtation – I Should I Think I Wish. Barely tolerating her assignment in the game, Tricia endures countless lines from Leif, all of which she casually bats away Don’t Bring Me Home to Your Mother. Anne finally breaks through Martin’s nervousness and with gentle cajoling learns that there’s a lot more to him than she anticipated. With his guard down, Martin admits part of his attraction to Anne is how simple and low maintenance she appears to be, despite her good looks – Plain Jane. Eve, aided by a few drinks, fully trashes her boyfriend which Chad endures. He lets Eve know he doesn’t care about her boyfriend and she clearly deserves better. I Should I Think I Wish (Reprise). As they draw closer, Eve kisses Chad, which is witnessed by the increasingly frustrated Tricia. Tricia starts to leave but is interrupted by a phone call from her boyfriend. Her immediate rage is quickly soothed and she starts to ask if he’s home and lonely, which is overheard by Leif. Leif takes her phone and hangs it up, pleading that her boyfriend will never change. Leif doesn’t care that she won’t go home with him, as long as she doesn’t go back to him. Tricia yells at Leif to leave and she is once again alone. Martin brings a round of drinks back to Anne and is surprised she has not run from him yet. Anne has already lost the game and has feelings for Martin, which she guards, but she remains friendly. Anne admits being with Martin is the first time she’s felt appreciated for who she is – not just the pretty girl. Martin impulsively kisses her and Anne reciprocates. Elated, Martin pulls out his mother’s wedding ring and asks if she’ll take it. Anne is beyond surprised, but can’t bring herself to say no. She smiles, accepts the ring, and they kiss. Tricia having witnesses this coupling and upset with her conversation with Leif sits and questions her life choices. Nobody Told Me. As the song ends, she admits defeat and calls out to Leif – asking him to leave with her.
One week later.
Eve introduces the new scene as a dream sequence. She’s joined by the ensemble as they sing the virtues of being a bride and having a garish wedding - Sweeter Than Sweet. As the dream sequence ends, the girls are back in the bar and Eve is extending her now ring adorned finger. She admitted last week’s encounter with Chad to her boyfriend – spurning him to propose immediately for fear of losing her. Martin enters and automatically sits with Anne, holding her hand. He notices the ring is gone and deduces what has happened – she’s too embarrassed to admit to her friends what happened. Be Careful What You Wish For. As Eve and Tricia exit, Martin and Anne argue. Martin wants the ring back and Anne counters that she is scared and leaves. Chad enters with his new girlfriend Jenny. He makes a show of her age, attractiveness, and the sarcastically points out the facts that led to Eve’s proposal. As Jenny gets a round of drinks, the argument intensifies between Chad and Eve – Only One with a Dream. Jenny returns and sends Chad away to cool his head. She and Eve explore the events that led up to the proposal and the reality that Eve will likely never actually get married. Jenny laments on her past, having already been divorced at an early age, and advises Eve to never settle. Chad returns and apologizes. Jenny exits to the restroom and informs Chad they are running late for their date. As Jenny exits she bumps into Leif, who immediately tries to woo her. Jenny turns the tide, knowing Leif’s name and his next line. When she identifies herself as a previous one night stand, she asks him how many girls heard “I love you” as he ran out the door – I Thought I Heard. She leaves to find Chad as the song ends. Chad and Eve mutually apologize and share a fond idea of what could have been between them. At a corner table, Anne has finally tracked down Martin and demanded the ring back. They admit their mistakes in this situation, but realize their attraction and affection towards each other still remains. They agree to start over and date and see how their relationship goes at a less rushed pace – Definitely, Maybe. Leif enters and finds Tricia. He gently asks if she returned home. Tricia admits nothing will change in her world and she simply needs to accept that this is her life. Leif shares the story of his encounter with Jenny and how he did not realize the power of his words and who he is hurting – Next. Tricia joins in the final chorus of the song as they both ask the question – have I ever said I love you and meant it? Tricia agrees to go on a date with Leif and gets one more drink as gets his car. Surprised by how life has given her a clean slate, she leads the ensemble as they lament on the new changes in their lives– One More Round.