6 Movies That Celebrate Singledom

The Break-Up (2006)

Directed by Peyton Reed, and intended as an ‘anti-rom-com’ of sorts, The Break-Up stars Vince Vaughn and Jennifer Aniston as a co-habiting couple whose relationship comes to a slow, painful end.

Gary Grobowski (Vaughn) runs a tour guide company with his brothers (played by Cole Hauser and Vincent D’Onofrio), while Brooke Meyers (Aniston) manages an art gallery for outlandish artist, Marilyn Dean (Judy Davis) – who is having a fabulous time being single, as it happens.

Gary is a self-centred, immature, slovenly individual, while Brooke is an ambitious, perfectionist who seeks a level of emotional intimacy that Gary is ill-equipped to provide. Inevitably, their incompatibility becomes too great to ignore, and Brooke ends their relationship. Both, however, refuse to leave their shared condominium.

When a last-ditch attempt to resuscitate their fading union spectacularly fails, the couple finally part ways, having come to understand the reasons why their relationship didn’t work. We see Gary and Brooke move on individually, and achieve the things in life they had been holding each other back from – making them far happier, and more contented in singledom than they ever had been as a couple.