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Katie, an aspiring romance novelist, is determined to lose her virginity for her book.

Katie's insecurities about her "skills" in a new relationship make her second-guess her writing as a live reading approaches. Victoria's exceptional "skills" get in the way of meaningful connections.

On Katie's 30th birthday, she decides tonight is the night to lose her virginity but is haunted by her cake. Victoria prepares to seduce a long-lost crush who's coming to town.

Katie discovers that things are not what they seem with Holden, while a secret admirer readies a grand gesture. Victoria tries to find a way to restore her virginity.

As the deadline for Katie's rewrite looms, Katie has an unusual proposition for her friend Kyle. Victoria struggles to find her place in their friendship.

It's the day of Katie's deadline, and she decides she has nothing left to lose but to follow her heart.