The Love Wager

Hallie wakes up in Jack’s bed in his hotel room. She recalls that they had sex several times the night before, including in the service elevator. Believing Jack is sleeping, Hallie crawls around the floor looking for her clothes. She can’t find her bra, so she leaves without it, as she doesn’t want him to wake up. As she makes her walk of shame through the hotel lobby, where employees recognize her, Hallie realizes that “she had just woken up in the hotel room of a guy whose full name she didn’t know” (16).

Jack arrives at the family wedding breakfast with a hangover. His older brother, Will, teases him, along with Colin, his best friend and now brother-in-law. Olivia tells Jack not to rush into another relationship just because he’s sad and doesn’t want to be alone. Olivia knows Jack was forcing his relationship with Vanessa. Olivia has enrolled him in a dating app and wants Jack to try it.

A week later, Hallie talks with her friend Chuck over dinner. She tells him that waking up in a stranger’s bed was the impetus she needed to turn over a new leaf and start living like an adult. Chuck, who is in a committed relationship with Jamie, encourages Hallie to try the dating app Looking4TheReal, and Hallie admits to herself that she wants love. Chuck describes the dating app as “shopping for the one person in the universe who will make you blissfully happy for the rest of your life” (23). Hallie says she’ll try it.

Ruthie, Hallie’s eccentric, impulsive roommate, serves Hallie banana bread. Hallie doesn’t know how to tell Ruthie she wants to move into her own apartment. Ruthie, who is a member of a secret fight club and rides a motorcycle, is unpredictable and lively. Hallie discusses profiles she’s finding on the dating app with Chuck, noting how all the men seem to be holding a beer or a dead animal. She runs across Jack’s profile and is surprised, as “[h]e’d seemed too confident and dashing to be single” (29). Then she recalls that a week ago, he was ready to be engaged, and now it seems he’s ready to date again.

Hallie teases Jack with a message asking why he hasn’t called. When he hesitantly responds, Hallie assures him she does not want to date him; privately, she thinks of their time as a throwaway one-nighter. She assures Jack she had a fine time but assumes the night only seemed red-hot because she was drunk. Jack teases her back, saying he still has her bra, and he was awake when she made her getaway. She asks what he is looking for, and he admits he wants someone important in his life. Hallie wants the same thing, but she suspects Jack is just in desperate need of a relationship and assures him she’s not interested in him. Jack enjoys their exchange; Hallie has “reminded him that fun was a thing” (33). Jack feeds his newly adopted cat, Meowgi.

Hallie cuts her hair, buys new clothes, and quits her part-time jobs to focus on her full-time one. She puts a deposit on her dream apartment and feels things “falling into place” (35). She gets ready for her date with Kyle, though she isn’t sure he’s the type to banter. She chats via text with Jack, who teases her for settling for someone “nice,” and she teases him for using the expression “getting railed” (37). Jack also has a date and is worried there won’t be chemistry. He teases Hallie about being his tiny bartender, or TB.

Jack tells Colin that he’s been chatting with the wedding bartender. Colin and Olivia had to delay their honeymoon trip because their driver ran over Olivia’s foot the morning they were supposed to leave. Jack reflects on his time with Vanessa as a lapse in judgment and wonders if he’ll make the same mistake again. He isn’t sure what he’s rushing toward.

Hallie approaches her date ready for magic, but Kyle is disappointing. He’s stingy and is insulted when Hallie, a tax accountant, won’t agree to do his taxes for him. She and Jack text about their failed dates, and Hallie asks how he can feel ready to date again; she thinks, “He clearly had I-can’t-be-single issues” (46). Jack admits he and Vanessa were going through the motions but weren’t close, and Hallie sees a parallel in her relationship with Ben. She shares that she is looking for “[s]omeone who likes [her] more than everyone else in the world” (48).

Jack proposes a bet on who will find their dream person first. Since he canceled his honeymoon, he offers Hallie his airline points. Hallie wants to travel to Paris. Hallie offers him a baseball signed by the Chicago Cubs after they won the World Series, which she took from Ben. They start calling each other Piper and Marshall. Hallie gives Jack her phone number, and he calls to invite her to go with him to a speed dating event.

Hallie meets Jack for the speed dating event, and he is even more handsome than she remembered. She likes his mischievous, teasing manner but tells him she finds him unattractive. Jack backs Hallie up when she argues with the speed date moderator about the logistics of who sits and who moves. He realizes, “he was having a great time just watching Hallie be Hallie” (60-1). Hallie’s first date, Blayne, is into yoga, and Jack’s tells him up front she just wants to be married. As they confer after, Hallie approves Jack’s Pretty in Pink reference. Hallie provokes her second date, Thomas, into walking away, while Jack’s date is scrolling on her phone. Hallie and Jack agree that if their next dates aren’t interesting, they’ll leave. Hallie’s next date, Nick, lives off a trust fund and plays video games all day. Hallie grabs Jack to make their getaway.

Hallie and Jack share tacos at the Taco Hut, where Hallie instructs Jack that cheese should go on the bottom of a taco, where it can melt, rather than remaining on top, where it stays cold and hard. Hallie finds Jack much easier to be around than her ex, Ben. Hallie explains how she took several months after her breakup to enjoy her “winter” and improve herself “so [she’d] be ready to take on the world when [her] spring arrived” (72).

When Hallie is curious about Jack’s old apartment building, he takes her inside to meet Olivia and Colin. Jack admits to himself that Hallie is hot, but he doesn’t want to confuse their partnership with sexual attraction. Olivia takes Hallie aside to talk. Olivia explains that Jack felt abandoned when Olivia and Colin fell in love, then was shaken when their Uncle Mack died. Jack is eager to find someone special, and Olivia worries he will jump into another relationship too fast. Hallie calls it going for “low-hanging fruit.” She recalls Ben saying he was in love with the idea of Hallie, but not Hallie herself. Hallie teases Jack about his family’s allegiance to Chicago sports teams, then points out her new apartment building and thinks, “it was nice to have someone to dream with” (80).