It Happened One Valentine's: A reporter is recruited by a music manager to play cupid for two famous pop musicians over Valentine's weekend, but things get complicated when she realizes one of the musicians has fallen for her. Torn between her big career move and her growing feelings, she must choose between coercing him into a relationship he doesn't want or following her heart and making him her own Valentine.

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Some movies that have similar genres and were produced around the same time as It Happened One Valentine's include How to Be Single, Something from Tiffany's, Love, Classified, The Worst Person in the World, Palm Springs, La La Land.