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How to Be Single (2016)

Movies Like How to Be Single for Grown-Up Ensemble Rom-Coms

Ensemble rom-coms about independence, mismatched timelines, and adults figuring out love.

88% fit

Best first watch

Isn't It Romantic

Isn't It Romantic (2019)

88 min · IMDb 5.9 · RT 70%

Like the seed movie, this stays in New York and follows adults sorting out love, independence, and mixed signals with a lively supporting ensemble around the lead. Todd Strauss-Schulson pushes the idea further by dropping Natalie into a fantasy version of dating, where mismatched timelines and rom-com rules force her to define love on her own terms.

Watch if

Watch if you want independence, New York chaos, and adults mocking rom-com rules.

Skip if

Skip if fantasy rom-coms distract you from grounded adult love stories.

For you if

  • You want romance that leaves room for independence and mixed feelings.
  • You enjoy ensemble stories where different adults want very different kinds of love.
  • You need quick jokes, modern dating setups, and endings that feel earned.

Not for you if

  • You want one central couple and a straight line to the kiss.
  • You prefer sweeping melodrama over messy adult life choices.
  • You need low sexual content and completely family-safe humor.

How How to Be Single (2016) alternatives compare

Pick Isn't It Romantic if you want the fastest laughs and a big, self-aware setup. Go for The Broken Hearts Gallery for friend-group energy and a softer healing arc. Choose Holidate for mismatched timelines stretched across a year. I Want You Back works best if you enjoy messy adults making worse choices before they grow up. Can You Keep a Secret? is the easiest, smallest-scale workplace option.

Isn't It Romantic(2019)

How ensemble-focused is it?

Friend-group heavy

How high-concept is the setup?

Big fantasy hook

How messy are the adults?

Self-aware mess

How quickly does it move?

Starts instantly

The Broken Hearts Gallery(2020)

How ensemble-focused is it?

Social circle core

How high-concept is the setup?

Grounded with a twist

How messy are the adults?

Healing mess

How quickly does it move?

Easy mid-tempo

Holidate(2020)

How ensemble-focused is it?

Mostly a duo

How high-concept is the setup?

Clean dating gimmick

How messy are the adults?

Commitment-avoidant mess

How quickly does it move?

Seasonal rhythm

I Want You Back(2022)

How ensemble-focused is it?

Two leads, many targets

How high-concept is the setup?

Scheme-driven chaos

How messy are the adults?

Peak bad-idea mess

How quickly does it move?

Busy but longer

Can You Keep a Secret?(2019)

How ensemble-focused is it?

Very pair-focused

How high-concept is the setup?

Classic mistaken intimacy

How messy are the adults?

Embarrassed but functional

How quickly does it move?

Quick and light

Not sure what to watch?

Date night

The Broken Hearts Gallery (2020)

The Broken Hearts Gallery (2020)

It balances breakup baggage, flirtation, and hopeful adult growth without getting too cynical or too broad.

Quick watch

Isn't It Romantic (2019)

Isn't It Romantic (2019)

Its brisk runtime and fast joke rate make it ideal when you want something light and easy.

Friend group

I Want You Back (2022)

I Want You Back (2022)

The terrible plan, shifting loyalties, and ex drama give everyone something to laugh and argue about.

Find your pick

Do you want a rom-com that feels heightened and joke-heavy, rather than grounded and relationship-first?

Moments you loved

Best movies like How to Be Single (2016)

88% fit
Isn't It Romantic (2019) movie poster

1. Isn't It Romantic (2019)

88 min · IMDb 5.9 · RT 70%

Like the seed movie, this stays in New York and follows adults sorting out love, independence, and mixed signals with a lively supporting ensemble around the lead. Todd Strauss-Schulson pushes the idea further by dropping Natalie into a fantasy version of dating, where mismatched timelines and rom-com rules force her to define love on her own terms.

Watch if

Watch if you want independence, New York chaos, and adults mocking rom-com rules.

Skip if

Skip if fantasy rom-coms distract you from grounded adult love stories.

Where to watch

Rent / Buy
85% fit
Holidate (2020) movie poster

3. Holidate (2020)

104 min · IMDb 6.2 · RT 45%

This one taps the same modern dating pressure, but filters it through a yearlong holiday arrangement that makes the timeline itself part of the joke. Sloane and Jackson are adults guarding their independence while family expectations and seasonal rituals keep pushing them toward love, so the mismatched timing feels built into every chapter.

Watch if

Watch if mismatched timelines, holiday pressure, and guarded adults sound fun.

Skip if

Skip if you dislike fake-dating setups and broad family comedy.

Where to watch

Stream
84% fit
I Want You Back (2022) movie poster

4. I Want You Back (2022)

116 min · IMDb 6.5 · RT 87%

This has the same interest in adults whose life plans are suddenly out of sync, then turns that panic into a messier two-hander. Peter and Emma chase old relationships across crossed timelines, but the movie keeps steering them back toward self-knowledge, independence, and a version of love that fits their own terms instead of the expected script.

Watch if

Watch if you enjoy messy adults, ex drama, and friendship turning into love.

Skip if

Skip if secondhand embarrassment and sabotage plots wear you out.

Where to watch

Rent / Buy
82% fit
Can You Keep a Secret? (2019) movie poster

5. Can You Keep a Secret? (2019)

94 min · IMDb 5.4 · RT 30%

This is a smaller-scale fit, but it still speaks to adults figuring out intimacy while trying to keep control of their image. Emma's accidental honesty speeds past normal romantic timelines, and the story turns that panic into a light workplace rom-com about vulnerability, independence, and deciding what love looks like on your own terms.

Watch if

Watch if you want a breezy workplace romance with adult vulnerability.

Skip if

Skip if you want stronger ensemble energy and less one-couple focus.

Where to watch

Rent / Buy

Beyond movies

TV shows and books that scratch the same itch

Starstruck

Starstruck

TV Show · 2021

This series lives in the same modern rom-com lane as How to Be Single, with messy dating, mixed signals, and a lead who is still figuring out what kind of life she actually wants. Its sharp jokes and casual, adult take on relationships fit the hub well, and the push-pull between independence and romance feels very close to the movie's view of single life.

Prime Video and Max

Lovesick

Lovesick

TV Show · 2014

Lovesick is an ensemble romantic comedy built around timing, old flames, and friends stumbling through adulthood, which lines up well with the movie's interest in mismatched timelines and evolving ideas about love. It stays light and funny while giving each relationship room to feel specific and grounded.

Available for purchase on Prime Video and Apple TV+ and Google Play and Fandango

Survival of the Thickest

Survival of the Thickest

TV Show · 2023

This show fits the hub through its current, city-set dating life and its focus on a woman rebuilding her life after heartbreak with humor and self-respect. Like How to Be Single, it treats romance as one part of a bigger adult identity story, with strong friend dynamics and a lead learning how to define love on her own terms.

Netflix

This Time Next Year

Book · 2020

by Sophie Cousens

Minnie and Quinn spend years on very different tracks before a chance meeting on their shared thirtieth birthday turns fate into a funny, grown-up romance. Its bad-luck jokes, repeated near-misses, and focus on getting your life together while love catches up fit the same contemporary lane as How to Be Single.

Available at major bookstores

Common questions about movies like How to Be Single (2016)

What is the best movie like How to Be Single (2016)?

Based on our analysis, Isn't It Romantic (2019) is the closest match with a 88% fit score. See the full breakdown above for why it earned the top spot.

Which of these works best if I'm watching with a partner or roommate?

The Broken Hearts Gallery and Holidate are the safest shared picks. They both keep the romance front and center, but they also leave room for friendship, family pressure, and adult uncertainty, so different viewers have different people to latch onto.

Which one should I avoid if I don't want a lot of awkward confession or breakup pain?

Can You Keep a Secret? leans hard on embarrassment, and I Want You Back gets pretty uncomfortable because the whole story runs on sabotage after a breakup. If you want the least emotionally bruised option, Isn't It Romantic keeps the hurt lighter and filters it through fantasy jokes.

What should I pick if I want to end the night feeling upbeat?

Isn't It Romantic is the easiest mood lift because it moves fast and treats love with a playful eye. The Broken Hearts Gallery also lands in a warm place, especially if you like stories where independence and community matter as much as the couple.

Which is the easiest weeknight watch, and which needs more attention?

Isn't It Romantic is the easiest toss-on choice because it is short, quick, and very clear about its joke from the start. I Want You Back asks for a bit more attention since the plan keeps shifting and several adult relationships are tangled together.

How different do these feel from each other?

Isn't It Romantic is broad and self-aware, while The Broken Hearts Gallery is softer and more grounded. Holidate plays like a seasonal dating experiment, I Want You Back pushes harder into bad-decision comedy, and Can You Keep a Secret? stays closest to a compact workplace farce.

Which one should I start with if I'm new to modern rom-coms?

Start with Isn't It Romantic if you want the most accessible entry point. Its New York setting, familiar rom-com jokes, and clear point of view make it easy to jump into, then you can move to The Broken Hearts Gallery or Holidate for more grounded adult timelines.

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Curated by the WeWatch editorial team

Ratings: TMDb · Streaming: JustWatch · Our methodology

Updated Jun 25, 2026, 4:46 PM UTC · Availability checked May 29, 2026, 10:37 AM UTC