70-year-old widower Ben Whittaker has discovered that retirement isn't all it's cracked up to be. Seizing an opportunity to get back in the game, he becomes a senior intern at an online fashion site, founded and run by Jules Ostin.

Judith has known her husband Brice since they were children, but now their marriage is growing stale. Having just completed her graduate work in psychotherapy, she's eager to begin a career as a marriage counselor. She takes an internship at a matchmaking firm for millionaires and meets Harley, a charismatic billionaire investor who makes no effort to hide his attraction to Judith. Although quite resistant at first, eventually Judith succumbs to his charms, placing her marriage in jeopardy and forever altering the course of her life.

Two recently laid-off men in their 40s try to make it as interns at a successful Internet company where their managers are in their 20s.