The Love Wager

Jack Marshall is the male romantic lead and the second protagonist of the novel. He is one of three children, with an older brother, Will, and a younger sister, Olivia, who is married to Colin, Jack’s best friend and former roommate. Jack’s parents still live in Omaha and Jack has a good relationship with them, sharing an interest in sports with his father with a special like for Chicago teams. Jack has a successful career as a landscape architect, holding a master’s degree in the field, and he has designed several notable public spaces.

Jack is very good-looking; Hallie calls him “too attractive for human eyes” (5). She notes, “He was tall, dark-haired, and handsome […] But there was something about his face that screamed mischief” (54). He also has all-around guy appeal; Hallie thinks, “He looked like the kind of guy they’d cast in a commercial for grabbing beers with the guys or picking up two-by-fours at a home improvement store” (89). But he also looks good when he dresses up; at her sister’s wedding, Hallie thinks, “He looked like a cologne ad. He looked like the guy who’d be on the cover of a romance novel about billionaires. He was dashing and gorgeous” (235). This shows that Jack’s appeal works on several levels. He is sincere but doesn’t take himself too seriously, and he has a sense of humor that matches Hallie’s.

Jack’s breakup with Vanessa at the beginning of the novel makes him aware of the flaws of that relationship and how it was mostly founded on his hopes rather than actually liking her. He hopes to remedy that with his next relationship. Jack is eager to find love, in part motivated by a fear of loneliness and the sense that his life will hold less meaning if he doesn’t have a committed partner. Jack always admired his Uncle Mack, who was a bachelor and the life of the party, but the fact that only his family attended Mack’s funeral convinces Jack that casual relationships aren’t enough. He’s drawn to Hallie not because of her looks but because he finds her personality and her approach to the world so appealing; her looks, and their sexual chemistry, are a bonus. Jack’s character arc in the novel involves being honest with himself about his feelings and learning to be vulnerable with another person. He realizes that friendship is the best ground for a romantic relationship, and he finds that with Hallie.

Olivia is Jack’s sister, a supporting character who plays the role of mentor as well as providing a model, with her and Colin, of a loving, playful, and successful committed relationship. In Mr. Wrong Number, where she is a protagonist and romantic lead, Olivia is portrayed as a clumsy person with bad luck. This characterization continues with the humorous disaster of her getting her foot injured by the driver who is supposed to take her and Colin to the airport for their honeymoon. This accident leaves Olivia on hand to provide advice to Jack and become a sounding board for Hallie, helping Hallie realize that Jack has tended to rush into relationships and might view Hallie as “low-hanging fruit” (261).

While Olivia is protective of Jack, she also wants what is best for him and prompts him to be honest with himself and his feelings. Olivia is the one who suggests Jack sabotage Hallie and Alex, thus introducing further conflict into their relationship, but she is also the voice of reason who tells Jack, later, to confess his feelings, choosing honesty with Hallie and himself. At the end of the book, while Olivia continues to tease Jack at the family celebration, she appears to have accepted Hallie into the family, confirming the success of their relationship.

Ruthie, as Hallie’s roommate, plays the role of supporting character and eccentric sidekick. Her portrayal is a caricature, an assemblage of characteristics that introduce a note of absurdity into the humor. Ruthie is adventurous and abrupt in her manner. She drives a motorcycle that she calls a hog, which is meant to indicate toughness, and she is also a member of a secret fight club. She leaves for long-term travel or dangerous activities at a moment’s notice, and she is impulsive and easily bored.

All of these qualities present a contrast to Hallie, demonstrating that as much as Hallie might worry she is a shit show, she is at least more conventionally stable than Ruthie and interested in more conventional things. Ruthie provides comic relief as well as being a foil for Hallie, and she also moves the plot forward by helping Hallie find Tigger the cat, one step further in Hallie’s process of maturing into adulthood and being open to love.