Aspiring romance novelist Katie 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 is 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.