NoBadPicks

Movies Like The Five-Year Engagement

If you loved The Five-Year Engagement's Comedy and Romance storytelling, these films deliver a similar experience — carefully selected for tone, themes, and emotional depth. Each pick includes where to watch it right now.

Top Picks

My Best Friend's Wedding
6.6

My Best Friend's Wedding

1997

When she receives word that her longtime platonic pal Michael O'Neal is getting married to debutante Kimberly Wallace, food critic Julianne Potter realizes her true feelings for Michael -- and sets out to sabotage the wedding.

Always Be My Maybe
6.6

Always Be My Maybe

2019

Reunited after 15 years, famous chef Sasha and hometown musician Marcus feel the old sparks of attraction, but struggle to adapt to each other's worlds.

Jexi
6.8

Jexi

2019

Phil's new phone comes with an unexpected feature, Jexi...an A.I. determined to keep him all to herself in a comedy about what can happen when you love your phone more than all else.

Love, Weddings & Other Disasters
6.0

Love, Weddings & Other Disasters

2020

A fussy celebrity caterer, a blind woman, a tour-bus guide and an inexperienced wedding planner search for love.

The Ugly Truth
6.5

The Ugly Truth

2009

A romantically challenged morning show producer is reluctantly embroiled in a series of outrageous tests by her chauvinistic correspondent to prove his theories on relationships and help her find love. His clever ploys, however, lead to an unexpected result.

The Incredible Jessica James
6.2

The Incredible Jessica James

2017

Burned by a bad breakup, a struggling New York City playwright makes an unlikely connection with a divorced app designer she meets on a blind date.

Looking: The Movie
7.2

Looking: The Movie

2016

Patrick returns to San Francisco for the first time in almost a year to celebrate a momentous event with his old friends. In the process, he must face the unresolved relationships he left behind and make difficult choices about what’s important to him.

Picture This
6.1

Picture This

2025

Single and without a man on the horizon, Pia runs a failing photography studio in London with her best friend Jay. As her sister Sonal prepares for marriage and her mother Laxmi urges her to partner up, a spiritual guru predicts Pia will meet the love of her life among her next five dates. With her family intervening, Pia embarks on a hilarious yet heartfelt quest for love.

More Movies Like The Five-Year Engagement

Zoey 102
6.8

Zoey 102

2023

Pacific Coast Academy alumni return to Malibu for an over-the-top wedding that turns into a high school reunion for the books.

The Woman in Red
6.2

The Woman in Red

1984

When a happily married family man, who would never consider an affair, meets a beautiful woman in red, he is totally infatuated and desperate to make her acquaintance. However, as he tries out various schemes to sneak out to meet her, he realizes that adultery is not quite as easy as it looks.

Materialists
6.4

Materialists

2025

A young, ambitious New York City matchmaker finds herself torn between the perfect match and her imperfect ex.

A California Christmas: City Lights
6.6

A California Christmas: City Lights

2021

Follows Callie and Joseph one year after they fell in love, now running a dairy farm and winery, but their romance is threatened when business and family obligations call Joseph back to the city.

Table 19
5.9

Table 19

2017

Eloise, having been relieved of maid of honor duties after being unceremoniously dumped by the best man via text, decides to attend the wedding anyway – only to find herself seated with five fellow-unwanted guests at the dreaded Table 19.

Playing It Cool
5.9

Playing It Cool

2014

A young man meets and instantly falls in love with an engaged woman.

Romance & Cigarettes
6.0

Romance & Cigarettes

2005

Ironworker Nick lives with his wife, Kitty, and three daughters. When he meets a significantly younger woman, Tula, he starts an affair with her, much to the chagrin of his wife, and his life is thrown into upheaval. Kitty kicks Nick out of the house, and he is forced to make some difficult decisions.

Sweet November
6.9

Sweet November

2001

Nelson is a man devoted to his advertising career in San Francisco. One day, while taking a driving test at the DMV, he meets Sara. She is very different from the other women in his life. Nelson causes her to miss out on taking the test and later that day she tracks him down. One thing leads to another and Nelson ends up living with her through a November that will change his life forever.

We Are Your Friends
6.8

We Are Your Friends

2015

Young Cole Carter dreams of hitting the big time as a Hollywood disc jockey, spending his days and nights hanging with buddies and working on the one track that will set the world on fire. Opportunity comes knocking when he meets James Reed, a charismatic DJ who takes the 23-year-old under his wing. Soon, his seemingly clear path to success gets complicated when he starts falling for his mentor's girlfriend, jeopardizing his new friendship and the future he seems destined to fulfill.

The Good Heart
6.4

The Good Heart

2009

Jacques is the curmudgeonly owner of a gritty New York dive bar that serves as home to a motley assortment of professional drinkers. Jacques is determinedly drinking and smoking himself to death when he meets Lucas, a homeless young man who has already given up on life. Determined to keep his legacy alive, Jacques deems Lucas is a fitting heir and takes him under his wing.

Pretty Woman
7.5

Pretty Woman

1990

Vivian is a carefree, streetwise diamond in the rough when she meets sophisticated billionaire Edward in a chance encounter that turns into a week-long business arrangement. But Vivian's energetic spirit challenges Edward's no-nonsense approach to life, and soon they are teaching each other – and falling in love!

Waiting for Forever
5.9

Waiting for Forever

2010

A Hollywood-set romantic tale of a guy who is content to live his life without a job yet with the love of his life, a young actress.

Why These Movies Are Similar

These recommendations share core qualities with The Five-Year Engagement (2012): Comedy and Romance themes, similar narrative structure, and comparable emotional depth. NoBadPicks uses a combination of TMDB collaborative filtering, genre matching, and AI analysis to surface films most likely to resonate with fans of The Five-Year Engagement.

See full details for The Five-Year Engagement (2012)

People Also Search For