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Photographer Matt Crisp grew-up believing his Mother died of a broken heart. That's why he's never been willing to risk his best friend Maggie's heart on a chance at true love. But when Maggie gives up on Matt, he desperately seeks help from his Wiccan best friend, Lisa, whose Entwined Hearts charm will either guide him to overcome his phobia & win Maggie back or drive him insane.
Devastated as a young boy by the realization his Mother died of a broken heart, Matt Crisp has never been willing to risk his best friend Maggie's heart on a chance at true love. Now, in their twenties, Matt’s hopelessly in love with Maggie yet pathologically incapable of admitting it. Maggie loves him too but she’s frustrated. She encourages Matt, one last time, to abandon his phobia and admit he loves her. When Matt fails, Maggie starts dating a guy Matt can’t stand. Matt, with help from a Wiccan friend, wishes for a second chance with Maggie, (as long as he doesn’t have to admit he loves her). Matt’s wish is granted, yet this wish has a mind of its own. Matt is magically forced to re-live the last moment he spent with his Mother. He learns she was struggling with a heart defect, not a broken heart. Matt’s heart is freed, yet his wish won’t be finished with him until he receives true love’s kiss. Matt’s wish drops him back into every awkward moment with Maggie, when Matt should’ve admitted he loved her but couldn’t. Each do-over moment goes comically wrong, and makes winning Maggie back seem impossible. Will Matt’s broken heart be the end of him?