At the top of the show, Roland Newman enters a Midtown Manhattan city park holding an interoffice envelope and looking hopeful. As he reads the letter inside, his hope turns to despair— he realizes he has been passed over for promotion…for the third time! He calls his friend Guy Lassiter III (who is late meeting him for lunch) and, in describing what happened, Roland suddenly realizes that the reason others are being promoted instead of him is because he is single and they are married!

Since Roland is perpetually awkward with women, he starts to tell Guy he needs his advice— until beautiful, successful businesswoman Blair Beaumont suddenly appears. Roland recognizes that she is the perfect answer to his situation. He hangs up mid-sentence and tries to motivate himself to go over and talk to her (“Married Over Labor Day”). At the end of the song, he is still standing on the opposite side of the park when Guy enters and immediately approaches Blair— who rolls her eyes and exits quickly.

Once Guy understands Roland’s promotion problem, he suggests Roland get a dog as a chick magnet for his upcoming vacation in the Hamptons, then get rid of the dog at the end of the vacation (“Get A Dog”). Roland remains unconvinced until Blair reappears and, once again, he can’t work up the nerve to even speak to her.

So, the next day he buys a puppy— who is invisible to the audience— at a pet store near his office and brings him to the Hamptons for his August working vacation. Guy, who is also on vacation, meets the puppy and names him Cupid, “’cause he’s gonna shoot his dart, or arrow, or whatever the hell it is, and bring you a wife!” Cupid immediately pees and poops inside the house, so Roland takes him out for a walk to prevent more “accidents”— and runs into Blair! Blair doesn’t recognize Roland, but she is captivated by Cupid… until he nips her! In apologizing and introducing themselves, Blair encourages fellow workaholic Roland to enjoy the freedom she personally savors in the Hamptons by working at the beach or on his patio (“Freedom”), something her own job wouldn’t accommodate. He gathers the courage to ask her out, and they set a date for the following Friday when she returns for her regular weekend retreat. She also encourages him to hire a trainer for Cupid. As she exits, he marvels that he has accomplished his goal on the first day of vacation… and all because of his new, annoying puppy (“It’s Cuz of You”)!

The following day, Roland has his first dog-training session with the no-nonsense, slightly intimidating Miranda Kunkel, who owns “Good Dog.” She sees that Cupid is yet another sweet puppy owned by a clueless human (“All About the Dog”). She explains that it’s Roland’s job to train Cupid… and it’s her job to train Roland.

The following Friday, Blair is back in the Hamptons, but dealing with a problem at work, when Roland and Miranda appear in the middle of a training session with Cupid. As Roland makes swoony conversation with Blair about their date for that evening, he forgets about Cupid, who wanders off, eating garbage, as Miranda unsuccessfully tries to get Roland’s attention (“Street Trio”). After Blair leaves, Miranda scolds Roland for being distracted, and he fires back that Blair is the whole reason he is training Cupid— which, to Miranda, is certainly not an acceptable reason for training (“Because of Her”).

The following day, a disappointed Roland tells Guy that Blair had to cancel their date to take care of business in London… but the date has been rescheduled for the following Friday. He also complains to Guy that Cupid insists on sleeping in the bed instead of his crate, and Guy tells him to get Miranda to help him solve the problem (“Freedom a la Guy”). As Guy is leaving, Miranda shows up for another training session— and discovers that Roland has left a side door open. She lights into Roland about endangering Cupid, who could have wandered onto the highway or been attacked by foxes in the woods. When she accuses Roland of not doing his job to take care of Cupid, they have a fiery argument (‘Vacation/Training Tango”). At the end of the argument, seeing that Miranda is about to walk out on him, Roland apologizes and begs her to continue training. She agrees… and also reluctantly agrees to do an overnight training to help him solve Cupid’s refusal to sleep in his crate.

That afternoon, Blair texts Roland from London to tell him she’ll be back the following weekend… for a whole week!

That evening, Miranda’s solution for Cupid sleeping in his crate is to calm him down beforehand, and she shows Roland how to make up a lullaby to do that (“Cupid’s Lullaby”). By the end of the lullaby, Cupid is asleep in Miranda’s arms— and Roland is asleep on his bed. As Miranda leaves for her night in Roland’s guest room, Roland starts to dream. His dream begins with Blair wafting in seductively— then Guy joins in… and ends up attaching a dog collar to Roland’s neck. And finally— Miranda enters, in a dominatrix outfit, ordering Roland to follow the commands she’s been teaching Cupid (“The Nightmare”).

He wakes from the nightmare with a scream and changes into a robe. He enters his kitchen to find that Miranda is also awake… because of his snoring. They start talking and, in their conversation, each discovers that the presumptions they had about the other were wrong. Roland isn’t privileged— his parents are working class and he himself worked his way through law school. Miranda, however, was raised in a privileged environment, which she rejected, in part because of her father’s disregard for her feelings when he gave away her dog as a child, without warning or discussion.

There is a moment of tension when Miranda challenges Roland’s idea that he has to get married, “fast,” to become partner. But that tension dissipates when Roland mentions how much Cupid adores her and compliments her training. And when Roland insists— against Miranda’s training advice— that he bring a now-whining Cupid into the kitchen because “he might be scared,” Miranda sees a completely new side of him that she never expected. As they sing Cupid back to sleep together, Roland looks at Cupid with deeper affection… and Miranda finds herself looking at Roland (who is unaware) with that same level of affection (“Cupid’s Lullaby Reprise”).

The following Friday, Roland prepares excitedly for his date with Blair as Guy mixes a “deadly batch of margaritas.” Guy leaves just before Blair arrives. Although Roland’s nerves get the better of him at first, his newfound command of Cupid is noted by Blair, and that gives him the courage to begin a calm conversation, to get to know her better. However— Blair isn’t interested in conversation. After suggesting Roland put Cupid in his offstage crate, which he quickly does, she surprises Roland by turning into a new, kinky Blair who is turned on by animal noises (“Let’s Make Some Noise”). The song culminates in a joint howl… and Cupid, offstage, joins in the howling. Roland is concerned enough to interrupt the date to make sure Cupid is okay… and Blair isn’t pleased. She starts to leave but, as he starts to panic, she reminds him she’ll be in the Hamptons all week and suggests they make another date for Sunday, since she will be having dinner the following night, Saturday, with her cousin.

On Saturday night, Guy and Miranda both end up in the Giddyap Bar. Although their initial conversation is rocky, the ice is broken once they find out they have each been stood up. They end up commiserating and dancing together, and finally, doing shots after she finds out Roland and Blair have, according to Guy, “howled together” (“Better Saturday Nights”).

However, when Guy mentions that Roland intends to get rid of Cupid the following week when he returns to the city, Miranda’s mood changes abruptly and she leaves. Guy stays long enough to see Blair enter and target someone at the offstage bar.

The next day, Guy shows up to tell Roland about Blair, loses his nerve, and tells Roland instead about having seen Miranda at the Giddyap. But after Guy sees Roland’s investment in Blair is continuing, he reluctantly tells a crushed Roland about seeing Blair “all over” a stranger at the bar, and then leaving with him. Guy leaves, and Roland calls Blair to confront her. She explains she’s not looking for a serious relationship and sees nothing wrong with sleeping with anyone she’s attracted to. Roland realizes he wants a serious relationship, and breaks up with her. He then calls Miranda and cancels not only their session for the day, but all their remaining sessions, since he has decided to return to the city early, having failed in his finding-a-wife goal.

The next day, Roland and Guy return from the gym, with Roland realizing that Blair wasn’t the right woman for him. When Cupid doesn’t greet them as usual at the door, barking, Guy notices the side door open and says jovially that now Roland won’t have to get rid of Cupid. Roland, furious and panicked, says he wants to find Cupid, not get rid of him, and he and Guy both run out opposite doors to search (”The Search”). When they return late in the evening, unsuccessful, Guy convinces Roland to stay home with the doors open rather than driving around in the dark, while Guy makes up Lost Dog posters and puts them up around town. After Guy exits, Roland sings about realizing what’s important to him— not his career, but Cupid (“Please Come Home”).

The next morning, Miranda finds Guy in the street hanging a poster. He explains to her that Roland left a door open and Cupid is missing, and that Roland is a wreck. Once she finds out that Roland actually doesn’t want to get rid of Cupid, she offers to join in searching.

Later that morning, Roland finishes his fifth call to the police department hoping for word of Cupid when Miranda enters… with Cupid! She tells him that she has had Cupid the whole time— she climbed in through the guest room window and left the door open, to rescue him. As Roland threatens to call the police, she reminds him that he told her he was only training Cupid to get Blair and that Guy made it clear he had “gotten” Blair. Roland corrects her and says nothing ever started with Blair and, as Miranda starts a heartfelt apology, Guy rushes in. Cupid runs to him and there’s a happy uncle-nephew moment.

Guy, in searching the woods, has gotten poison ivy and asks, “Who is gonna sleep with me now?!” To which Roland replies, “Maybe you need more than a one-night stand,” and sings, “Get a dog!” He is interrupted by the doorbell and Blair running in to ask about Cupid— who runs to her. When she remarks about how wonderful it must be to have so much love, Miranda replies, “Get a dog!” and Roland and Guy chime in (“Get A Dog - Reprise”).

Blair and Guy both realize they might be ready to get dogs… and (with Roland’s approval) they leave together. Miranda starts to leave too, but, as she approaches the door, Roland realizes he doesn’t want to see her go! He, for once, manages to find just the right words. And she says yes to a date over Labor Day weekend (“Finale”). As Miranda exits smiling, Roland holds Cupid tight and hums the theme to “Married Over Labor Day.”