6 Best Ensemble Holiday and Love Story Movies

By Vlad Zakh · June 5, 2026

Romance feel good

Put a big cast into one holiday and you get a pile of tangled love stories. Valentine’s Day, New Year’s Eve and Mother’s Day all weave several stories together over a single day, Love Actually is the template, and He’s Just Not That Into You adds dating advice to the mix. Crazy, Stupid, Love. is the sharper entry, with a suddenly single man learning to date from a smooth-talking bachelor.

Mother's Day (2016) 01

Mother's Day (2016)

TMDB ★ 5.1

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

Directed by Garry Marshall · 1h 58m · Rated PG-13

Where to watch

Stream: Netflix, fuboTV, Netflix Standard with Ads · Rent or buy: Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home

New Year's Eve (2011) 02

New Year's Eve (2011)

IMDb ★ 5.6 RT 7% Metacritic 22

An ensemble cast's lives converge in Times Square during the countdown to midnight.

Directed by Garry Marshall · 1h 58m · Rated PG-13

2 wins & 9 nominations

Where to watch

Rent or buy: Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home

Crazy, Stupid, Love. (2011) 03

Crazy, Stupid, Love. (2011)

IMDb ★ 7.4 RT 79% Metacritic 68

A newly single father is mentored in dating by a serial womaniser, with unexpected romantic tangles all round.

Directed by Glenn Ficarra & John Requa · 1h 58m · Rated PG-13

5 wins & 23 nominations

Where to watch

Stream: HBO Max Amazon Channel, HBO Max · Rent: Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home, Spectrum On Demand · Buy: Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home

Valentine's Day (2010) 04

Valentine's Day (2010)

IMDb ★ 5.8 RT 18% Metacritic 34

A dozen intersecting Los Angeles couples navigate one chaotic Valentine's Day.

Directed by Garry Marshall · 2h 05m · Rated PG-13

7 wins & 12 nominations

Where to watch

Rent: Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home, Spectrum On Demand · Buy: Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home

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

He's Just Not That Into You (2009)

IMDb ★ 6.4 RT 42% Metacritic 47

Several overlapping Baltimore relationships all struggle with the same brutal dating truths.

Directed by Ken Kwapis · 2h 09m · Rated PG-13

1 win & 4 nominations

Where to watch

Stream: fuboTV, Paramount Plus Premium, Paramount Plus Essential, Paramount+ Amazon Channel, Paramount+ Roku Premium Channel · Rent: Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home, Spectrum On Demand · Buy: Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home

Love Actually (2003) 06

Love Actually (2003)

IMDb ★ 7.5 RT 65% Metacritic 55

Ten overlapping London love stories converge in the weeks before Christmas.

Directed by Richard Curtis · 2h 15m · Rated R

Won 1 BAFTA Award11 wins & 30 nominations

Where to watch

Stream: Netflix, Netflix Standard with Ads, Starz, Starz Apple TV channel, Starz Roku Premium Channel · Rent or buy: Amazon Video, Apple TV Store, Google Play Movies, YouTube, Fandango At Home

Streaming availability data from JustWatch, via TMDB. Availability changes often, so check the service before you plan a movie night.

Vlad Zakh

Vlad Zakh

Founder, Movieix

Founder of Movieix. He started the site because most recommendation pages felt like noise. Here, lists are sorted by who's in the film, where it's from and what mood you're in tonight.