In Kentucky, a transgender woman and her best male friend lament the lack of eligible partners and step across old boundaries of love and romance.

Guerrino, a prematurely widowed businessman, falls in love with Chantal, a former paratrooper in the German army who changed sex a few years earlier.

Sam is a workaholic bachelor who babysits his niece and nephew before the holidays when his sister and her husband have to go out of town. Completely out of his element, he recruits help from their handsome neighbor Jason and finds himself in an unexpected romance.

Connor has a threesome with his long-time crush Olivia and an alluring stranger named Jenny. It surprisingly serves as the spark to a full blown relationship with Olivia, until both women end up pregnant and all three are thrust into a difficult journey toward new realities that none of them could have expected.

Journalist Fred Flarsky reunites with his childhood crush, Charlotte Field, now one of the most influential women in the world. As she prepares to make a run for the Presidency, Charlotte hires Fred as her speechwriter — much to the dismay of her trusted advisers.

An anxious New York law school dropout stumbles into a job babysitting his psychiatrist's three granddaughters and falls for the girls' mother, an actress in a rocky marriage.

A middle-aged husband falls for his childrens' teenaged babysitter.

Cal Weaver is living the American dream. He has a good job, a beautiful house, great children and a beautiful wife, named Emily. Cal's seemingly perfect life unravels, however, when he learns that Emily has been unfaithful and wants a divorce. Over 40 and suddenly single, Cal is adrift in the fickle world of dating. Enter, Jacob Palmer, a self-styled player who takes Cal under his wing and teaches him how to be a hit with the ladies.

Paul and Kim meet when their vehicles collide. Paul is fascinated with the attractive Kim. It turns out that the two were childhood friends in Catholic boys' school, but back then, before the operation, Kim was named Karl.

This sensitive and sensual film draws together several narratives spanning several decades, all of them transpiring in the same room of the same Singaporean hotel — and all of them involving sex.

Claire moves impulsively from NYC to Paris, where she nannies for the family from hell, battles wacky French bureaucrats, embarrasses herself in front of her Parisian crush, and navigates a toxic relationship—among other faux pas.

Three intersecting stories of transgender romance explore the boundaries of love, culture and identity across three generations.