The Love Wager

The Love Wager is a contemporary romantic comedy by Lynn Painter, the New York Times bestselling author of several romances for adult and young adult readers. The second in a series beginning with Mr. Wrong Number, The Love Wager follows one-time lovers Jack Marshall and Hallie Piper as they make a wager about who can find love first. As Hallie and Jack build their friendship through witty banter, pet adoption, and a shared love of tacos, the text suggests that good friends ultimately make the best lovers. Painter gently satirizes tropes of the romance genre, including fake relationships, one-bed scenarios, and confessions in the rain. 

This guide references the Berkley trade paper first edition published in March 2023.

Content Warning: The source material and guide feature substance use, sexual content, cursing, and discussions of emotional abuse.

Plot Summary

When Jack Marshall’s girlfriend breaks up with him at a wedding reception where he’s the best man, Jack talks the cute bartender, Hallie Piper, into drinking with him. After a one-night stand, Hallie sneaks out of his hotel room the next morning, forgetting her bra. Jack’s sister, the bride, makes him a profile on an online dating app. She wants him to meet someone while taking things slow.

Hallie is recovering from a breakup with a long-term boyfriend, Ben, and believes she’s ready to start dating again. On the advice of a friend, Hallie joins a dating app and gets in touch when she spots Jack’s profile. She suspects he’s one of those guys desperate to be in a relationship, and while she doesn’t consider him dating material, they exchange lively messages. Jack is laidback, witty, and easy to talk to, and after Hallie reveals that she, too, is looking for someone to be her favorite person, he proposes a wager. Whoever finds love first will win their bet. He offers Hallie his airline miles, and she offers him a baseball signed by the Chicago Cubs.

Jack invites Hallie to attend a speed dating event with him, but their encounters are terrible. They leave early to have tacos at a nearby restaurant. Jack introduces Hallie to his sister, Olivia, who confirms that Jack rushed things with his ex. Olivia hopes Jack won’t try to pursue Hallie just because she’s available. Hallie and Jack agree to set up their dates at the same restaurant: If their dates are disappointing, they’ll go get tacos. This results in many tacos and a growing bond. Hallie feels like she’s getting her life together: She moves into a new apartment, adopts a cat, and meets a guy, Alex. When Jack leaves town for a work trip, Hallie realizes he’s become her new best friend, and she misses him.

While he’s away, Jack reflects on the loss of his uncle, Mack, who made him realize that he longs for a relationship. He’s eager to see Hallie when he returns and is annoyed by Alex, who is serious about Hallie. When Jack informs Alex that Hallie only followed up with him because of their wager, Alex breaks things off with Hallie. She feels rejected and distraught that she won’t have a date to her sister’s destination wedding in Colorado, as Hallie’s ex, Ben, will be in the wedding party. Jack offers to go along and pose as Hallie’s boyfriend, pretending he’s madly in love from the minute they step through security.

Hallie is delighted at playing boyfriend-girlfriend with Jack, and the sexual chemistry between them is undeniable. Jack enjoys Hallie’s upfront, fun-loving nature, and she grows more attracted to him. During the rehearsal dinner, they sneak away into a housekeeping closet to discuss that they probably shouldn’t have sex, but then they kiss. Hallie suggests they could have sex without letting emotions get involved, but Jack knows it’s too late for him. He’s already fallen for Hallie, but he is reluctant to confess his feelings because she doesn’t seem to reciprocate them. He’s worried he’ll destroy their friendship.

The day of the wedding, Hallie decides she wants to try to make Jack fall in love with her. She flirts with him at the wedding reception, and they have sex in the freezer of the restaurant. In their hotel room, where there is only one bed, they enjoy their last night together, and they have sex the next morning in the shower. As they fly back to Omaha, Hallie realizes she is in love with Jack. When she runs into Alex at the airport, and he mentions that Jack told him about their wager, Hallie is hurt that Jack didn’t tell her about his part in her breakup. She fears that Jack is doing exactly what his sister Olivia said: clutching at Hallie because she’s nearby. Hallie worries Jack will end up realizing he doesn’t like her after all, just as Ben did. She knows this will devastate her and decides to end things. When Hallie offers one last night of sex, Jack doesn’t hesitate to take it, but he doesn’t reveal his feelings.

After two weeks of not talking, Hallie and Jack realize how much they miss each other. Jack shows up at a restaurant and sees Hallie on a date with Alex. When Jack leaves, Hallie runs after him in the rain. Jack confesses his feelings, Hallie admits hers, and they go get tacos.

In the epilogue, Hallie celebrates Christmas with Jack’s family, and Jack’s dad is happy to get the signed baseball as a gift. Jack’s gift to Hallie is a vacation back in Vail, the scene of her sister’s wedding. Jack feels like Hallie is his Christmas gift.