Anise was previously married to her high school sweetheart, who died in an accident when their children were young. After his death, Anise continued to pursue a college degree, which her husband had encouraged her to do before he passed). She graduated and eventually earned a doctorate, all while being a single mom.. Ury aims to help Anise shine in her “biggest, truest way” and urges her to not minimize her ambitions or achievements when looking for her next partner.

Suzanne is a widow who was married for 27 years and had three children with her husband, Chris. She describes Chris’ death as having the rug pulled from under her.  In her grief, she threw herself into her career and practice. But now Suzanne, a self-proclaimed optimist who leaves quite the impression with her big energy, big hair, and brightly colored lips, is ready to date again. She jokes that she’s looking for a Matthew McConaughey type.

Nate is a divorced father of two. He shares one daughter with an ex-girlfriend from college (who is now his best friend and confidant). He was later engaged to someone else, but it didn’t work out due to his former partner’s infidelity. Later, he married another woman with whom he had a second daughter; he and his wife stayed together for 16 years. Since their separation, Nate has been living a “peaceful life” in a man cave of a home that’s extremely tidy — or, as Ury puts it, “buttoned up.” Ury hopes Nate will let his guard down on dates, while Nate aims to work through his trust issues.

Pam has a big, storied life and a big personality to match  —  twice married and twice widowed,  she’s been single for 15 years and lives with her granddaughter, Zoe, in a rural countryside house full of memorabilia and animals. Pam’s first husband, Steve, was a rock musician who swept her off her feet; they had a son a year after they were married. After Steve’s death, Pam spent 21 years with her next partner, Will, before he died from a terminal illness. Ury describes Pam’s home as “a shrine to the past” and encourages her to focus on the future. On dates, Ury tells her to “be interested, not interesting.”

Lori is a divorced mom of two — a son, Sean, and a daughter, Kennede — who has been single for 15 years. She leads a double life: By day, she’s a student engagement and behavior coach. By night, she’s a celebrity correspondent at media events and press junkets, where she rubs elbows with the famous on the red carpet. Lori confides in Ury that she has intentionally stayed busy with two time-consuming jobs so that she doesn’t have to think much about dating. But now she’s ready for love again and, crucially, hopes to avoid getting friend-zoned by her crush.

Greg is twice divorced, has two sons with his first wife, and has been single for 12 years. He tells Ury that both marriages ended for different, stressful reasons. Once upon a time, Greg gave the dating apps a go, and while he initially enjoyed the feelings of “butterflies and bliss” that came with catching feelings for potential new lovers, he eventually became jaded and frustrated by all of the ghosting and messaging that went nowhere. Greg tells Ury that, for him, physical attraction is an important element in relationships, but Ury advises him to “expand his parameters.”