Laura talks with Maxine, who lived most of her life as a self-described "alpha male" until the day things just clicked. Then Laura sits down with The Naked Truth author Leslie Morgan Steiner. Leslie describes how she reclaimed her sexuality after her gray divorce, and teaches Laura how to open her eyes to the possibilities of making romantic connections. Laura also learns about making connections despite physical distancing from listeners like Robert, who gave virtual speed dating a go.

Laura talks with legendary women's college basketball coach Elaine Elliott, whose commitment to her partner endured long after the romance was over. Then, Norm and Jeanne share the story of how they built a solid partnership without mentioning the "C" word. Finally, Laura sits down with public radio icon Diane Rehm, who put her own modern spin on a traditional choice.

Laura talks with Ken, who's reluctant to date after feeling financially burned in his marriage; accountant and financial planner Colette Kolanko, who says we can find creative and loving ways to talk about money with a future partner; and Bob and Marge, who merged their lives without blending bank accounts.

Laura talks with Evamarie about the discovery that leads her to try online dating; Mark, whose search for love after devastating loss feels more urgent and also, elusive; and Girard, who gains romantic clarity after a health crisis.

Laura talks with Sandy, who shares how communication set the stage for her second 'first time,' and Dr. Jen Gunter, author of The Vagina Bible, and a leading advocate for communicating about women's sexual health. Then she debunks myths about male sexual health with Dr. Arthur Burnett, a surgeon and scientist whose research led to the development of Viagra. Finally, Laura learns about communication, intimacy and adult toys with Kathryn Ellis, an occupational therapist and sexuality counselor.

Laura talks with Steven, who tries bonding with his partner's vicious dog even as their marriage hits the rocks; Jamie, who offers to share her home with an unlikely housemate; and Jenevieve, who throws practicality aside to summon the online dating spirits.

Host Laura Stassi talks with New Yorker Dennis, who doesn't want to give up the single life. Maybe he's waiting for the perfect woman to finally become available? Then there's Michele in Washington, D.C. Despite successfully connecting people in her large professional and social circles, she hasn't made a romantic connection for herself. Finally, life coach Amy Schoen says people who want to couple up need to be intentional in thought and actions.

Host Laura Stassi attends her 40th high school reunion, where her former classmates open up about their own love lives and dating strategies. Then, she revisits a man she went on a date with to get schooled on online dating as well as the “three-date” rule. Finally, she gleans inspiration from a couple who met at the apartment building where they both live.