Marcus Graham is a successful advertising executive with a reputation for being a serial womanizer. However, when his new boss Jacqueline turns out to be a woman who treats men the way he treats women, Marcus is shocked and confused. Despite his best efforts, he finds himself falling for Jacqueline, but their relationship is complicated by his past behavior and her reluctance to commit. Meanwhile, Marcus also develops feelings for his colleague Angela, who is more interested in a genuine relationship than his usual conquests. As Marcus navigates his feelings for both women, he must confront his own emotional baggage and learn what it means to truly love someone. Will he choose the high-powered career woman or the down-to-earth beauty?

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Some movies that have similar genres and were produced around the same time as Boomerang include Moonstruck, Blue Juice, As Good as It Gets, Forrest Gump, When Harry Met Sally..., Career Opportunities.

Boomerang was released in theaters on June 30, 1992.