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Film: The Rebound

A 2009 romantic comedy starring Catherine Zeta Jones and Justin Bartha. Sandy divorces her husband and moves out with their children after finding him cheating, finding a demanding but successful job as a sports analyst. She hires the aimless twenty-something Aram to be a full-time nanny for her kids. They fall for each other but find romance hard to navigate.

This film provide examples of:

Bad Date: Most of Sandy's Blind Dates
Bedmate Reveal: In-universe, subverted. When Aram wakes up a hungover Sandy, she thinks she slept with him.
Blind Date: Sandy has a few. None go well.
Casanova Wannabe: Aram's workmate and friend Mitch.
Citizenship Marriage: Aram's previous marriage. He won't divorce her as it would mean she would get deported.
Distracted by the Sexy: Aram by Sandy's dancing in the club.
Family Versus Career: Applies to both Aram and Sandy. Sandy struggles to cope with both her job and raising her kids, leading her to hiring Aram. Aram chooses to stay with "his family" rather than take a high-paying corporate job. A rare example in which Sandy's choice to devote herself to her work is not portrayed negatively.
Happily Adopted: Zeke, Aram's son.
Hot Mom: Its Catherine Zeta Jones.
Jewish Mother: Aram has one. Though she's not too over-the-top.
Likes Older Women: Aram has significantly fewer issues with the age difference.
Masculine Girl, Feminine Boy: Sandy is the breadwinner and obsessed with sports. Aram takes care of the kids and gave up an awesome job to be with them.
May-December Romance: 15-year age gap.
Maybe Ever After: The ending.
Primal Scene: Sandy's son walks in on them having sex on the living room couch. Hilarity Ensues.
The Slacker: Aram, in a sympathetic version of the trope where he does not know what he wants to do with his life.
Someday This Will Come In Handy: Sandy's obsession with fantasy sports.
Travel Montage: Aram goes travelling, though he never rocks Cleveland.
Visit By Divorced Dad: Does not end well.