Five interwoven love stories explore the ups and downs of finding love. An unlikely relationship between two people who despise one another, letting go after the loss of a loved one, conquering fear and awkwardness to win over a crush, gaining the strength to move on from a loveless relationship and meeting the 'one' only to find out the timing couldn't be worse.
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Elizabeth's engagement plans are thrown into disarray when her fiancée's free-spirited brother David returns home. David's unexpected influence prompts Elizabeth to question her life decisions.
After drag racing his vintage convertible around Palm Springs, a retired NASA test pilot (William Shatner) loses his license. Forced to take public transportation, he meets Caroline (Jean Smart) and learns to navigate love and life again.