A struggling romantic accepts her aunt's wager: go on 40 dates in 40 nights to find true love. If she fails, her aunt will cover her rent and student debt. But the journey proves more challenging than expected.
Striving to be independent, the blind but determined Don Baker moves away from his overprotective mother. After settling into his new San Francisco digs, Don meets kooky neighbor Jill Tanner. Don's quick wit and good looks disarm the free-spirited Jill, and before long they're more than just friends. Will Mrs. Baker's incessant meddling destroy Don and Jill's budding relationship?
Gina hates her Valentine's Day birthday and travels to Greece to prevent her boyfriend's proposal. With help from vacationers Johnny and his sister Mickey, she schemes to delay it – while questioning her relationship.
Alex, Emily, and their son, RJ, are new to Los Angeles. A chance meeting at the park introduces them to the mysterious Kurt, Charlotte, and Max. A family “playdate” becomes increasingly interesting as the night goes on.