6 Best Ensemble Holiday and Love Story Movies

By Vlad Zakh · June 5, 2026

Romance feel good

The interwoven romantic lives of a sprawling ensemble cast has powered some of cinema’s most beloved holiday-set love stories.

Mother's Day (2016) 01

Mother's Day (2016)

IMDb ★ 5.1

The intertwined lives of several mothers and their families collide in the days leading up to Mother's Day.

New Year's Eve (2011) 02

New Year's Eve (2011)

IMDb ★ 5.6

The romantic lives of a sprawling group of New Yorkers intertwine over the course of one New Year's Eve.

Crazy, Stupid, Love. (2011) 03

Crazy, Stupid, Love. (2011)

IMDb ★ 7.3

A suddenly single middle-aged man is mentored in the art of dating by a smooth-talking bachelor.

Valentine's Day (2010) 04

Valentine's Day (2010)

IMDb ★ 5.8

The romantic lives of a sprawling group of Los Angeles residents intertwine over the course of one Valentine's Day.

He's Just Not That Into You (2009) 05

He's Just Not That Into You (2009)

IMDb ★ 6.5

The romantic entanglements of a group of Baltimore friends reveal the confusing signals of modern dating.

Love Actually (2003) 06

Love Actually (2003)

IMDb ★ 7.6

The romantic lives of eight very different couples intertwine in London during the weeks before Christmas.

Vlad Zakh

Vlad Zakh

Founder, Movieix

Founder of Movieix, built to fix a specific annoyance: most recommendation sites are just algorithm-driven noise. Our lists are researched and organized by who's in a film, where it's from, and the mood you're actually in tonight.