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The Ultimate ‘Guy and Girl’ Movie List for Date Night

Updated on June 6, 2025 by TMM Staff · Lifestyle

A couple relaxing in bed, watching Netflix on a laptop.
©Anastasia Shuraeva/Pexels.com

There’s nothing like good storytelling to get people reflecting about their own lives. How many times have you gone to see an excellent movie, only to find yourself and your companions talking about the plot and life lessons hours after it ended?

Table of Contents

Toggle
  • Celeste and Jesse Forever
  • (500) Days of Summer
  • Eternal Sunshine of the Spotless Mind
  • Her
  • Blue Valentine
  • La La Land
  • The Great Gatsby (2013)
  • Juno
  • Ruby Sparks
  • Definitely, Maybe
  • Closer
  • Easy A
  • About Time
  • One Day
  • Normal People
  • Pride and Prejudice (2005)

Here are 15 “guy and girl” films that will spark conversation between you and your partner, and maybe even help you see your relationship in a new light. Whether you’re newly dating or years into commitment, these movies pull back the curtain on love, timing, growth, and everything in between. Watch one, then talk about it. You might be surprised by what comes up.

Celeste and Jesse Forever

A man and a woman looking at each other intensely.
©Image: OpenAI

Starring Andy Samberg and Rashida Jones, Celeste and Jesse Forever is the story of a divorced couple trying their hardest to maintain a friendship despite their breakup. The film balances real heartbreak with dry humor and awkward moments that hit too close to home.

If you want you and your partner to talk about how you can avoid the common pitfalls for couples who have been together for forever, this one will get you thinking about emotional maturity, timing, and what “love” looks like when it changes form.

(500) Days of Summer

A couple and a dog watching the sunset over a city skyline.
©Image: OpenAI

(500) Days of Summer, starring Joseph Gordon-Levitt and Zooey Deschanel, is the story of a young man reflecting on the highs and lows of a past relationship. It plays with expectations of romantic tropes and leaves you with more questions than answers. 

It’s perfect for couples who want to talk about the difference between infatuation and compatibility, what happens when two people have varying degrees of readiness to commit, and how two people can experience the same love story very differently.

Eternal Sunshine of the Spotless Mind

A man walking on a snowy beach with a dark, cloudy sky.
©Image: OpenAI

A classic in the romantic drama genre, Eternal Sunshine of the Spotless Mind is the story of a couple who choose to erase each other from their memories after a breakup.

It’s visually striking, thought-provoking, and emotionally layered, raising questions about pain, healing, and the parts of love we try to forget. There’s a reason it’s become such a classic among film enthusiasts. You and your partner may find yourselves wondering: If you could start fresh, would you?

Her

A man with glasses and a mustache standing outside at night with a city in the background.
©Image: OpenAI

Starring Joaquin Phoenix and the iconic voice of Scarlett Johansson, Her explores a man’s intimate relationship with an AI operating system. Truly prescient considering the AI takeover that’s happened in recent years, it’s starts out as sci-fi, which eventually becomes a deeply emotional meditation on loneliness, identity, and evolving connection.

It’s a must-watch for couples interested in talking about emotional needs, the complexity of love, and what it means to truly be seen.

Blue Valentine

A man and a woman sitting separately on a bed in a dimly lit room.
©Image: OpenAI

Blue Valentine, starring Ryan Gosling and Michelle Williams, is the story of a relationship told in parts: Its euphoric beginning and painful unraveling. It’s raw, unfiltered, and doesn’t flinch from the hard stuff. It’s not the easiest viewing, and Gosling and Williams truly sell the parts of the unhappily married couple who’s seen the worst in each other.

If you’re ready for a more serious watch, this one opens up deep questions about effort, communication, and how love can sometimes fade even when both people want it to stay.

La La Land

A couple dancing under a starry night sky with city lights in the distance.
©Image: OpenAI

Starring Ryan Gosling and Emma Stone, this Oscar-winning musical film is as much about dreams as it is about love. With show-stopping visuals and bittersweet storytelling, it’s a love letter to ambition and the people who shape us. 

After watching, you and your partner might reflect on the sacrifices you’ve made–or would make–for each other’s goals and where love fits in the bigger picture. If you only had to choose one, which would you go for: Love or career?

The Great Gatsby (2013)

A man in a suit looking across a body of water towards a green light in the distance under a full moon.
©Image: OpenAI

Based on the novel by F. Scott Fitzgerald, this whimsical take on the story is both dazzling and tragic. It’s about wealth, obsession, and the illusions we build around love. It’s Baz Luhrmann at his spectacular best. 

Watching Gatsby’s pursuit of a romantic ideal will get you talking about whether people can really change, how nostalgia and fantasy shape our relationships today, and if you can truly love or know somebody that you put on a pedestal.

Juno

Two teenagers walking on a path surrounded by autumn trees and fallen leaves.
©Image: OpenAI

A beloved script by auteur Diablo Cody, Juno follows the life of a teenager navigating an unexpected pregnancy with sharp wit and surprising emotional depth. Though it’s full of humor, it also touches on intimacy, responsibility, and how people can show up for each other in unconventional ways. You’ll end up talking about partnership at any age, and how having a kid can truly change everything.

Ruby Sparks

A woman with red hair sitting on a couch in a dimly lit room with string lights.
©Image: OpenAI

Ruby Sparks is the story of a novelist who manifests his dream girl into real life, only to discover that fantasy and reality don’t always get along. It’s quirky and smart, with just enough edge to get you thinking about autonomy, control, and what it really means to love someone as they are, not as we want them to be.

Definitely, Maybe

A man and a young girl sitting on a couch, looking at each other and talking.
©Image: OpenAI

If you love a good mystery in film, this guy-girl story is for you. Told through flashbacks, it follows a father explaining his romantic past to his daughter. Sweet, charming, well-acted, and full of twists, it gets you thinking about how timing, choices, and honesty all shape a love story. You and your partner might end up comparing your own timeline. 

And if you haven’t talked about your exes? Doing so after watching this film may be the best time. 

Closer

A man and a woman sitting across from each other, looking intently at one another in a dimly lit room.
©Image: OpenAI

Directed by the late great Mike Nichols and starring a powerhouse cast including Julia Roberts, Natalie Portman, Jude Law, and Clive Owen, this romantic drama explores love, betrayal, and brutal honesty about the rigaudon romance between four people. It’s raw and uncomfortable, but in a way that invites real talk about trust, desire, and the price of truth in relationships.

Easy A

Emma Stone in a red dress and sunglasses walking down a hallway with surprised students looking at her.
©Image: OpenAI

This high school comedy is a coming-of-age spin on classic novel The Scarlet Letter, with Emma Stone in the role that made her a breakout star. It’s sharp, self-aware, and surprisingly insightful about reputation, sexuality, and self-worth.

Couples might find it surprisingly relevant, especially when it comes to navigating public perception versus private truth in love.

About Time

A man and a woman smiling and dancing in the rain.
©Image: OpenAI

Starring Rachel McAdams and Domhnall Gleeson, this beloved romantic comedy is about a man who can time travel and how he uses it to navigate love and family. More than just a clever concept, it’s a tender reminder that the best moments are often the ordinary ones. It’ll have you both reflecting on gratitude, presence, and how it’s the little things that cause us to build the life we’ve always wanted.

One Day

A man embracing a woman at a train station platform.
©Image: OpenAI

Based on the bestselling novel by British author David Nicholls and starring Anne Hathaway and Jim Sturgess, One Day is the story of best friends turned lovers, told over the same calendar date across many years. 

It’s a poignant look at friendship, missed chances, and the passage of time. You and your partner will probably talk about what keeps people connected, and what timing really means in love. (Watch out for the remake coming out soon, too!)

Normal People

A man and a woman standing under an umbrella in the rain, looking at each other.
©Image: OpenAI

Adapted from the fan favorite novel by Sally Rooney, Normal People follows the intense relationship between two Irish students as they grow into adulthood. It’s a tender, awkward, and painfully real look at romance, and will have you reminiscing about your growing up years, too. You and your partner might end up unpacking communication styles, emotional vulnerability, and how two people can grow apart, or together, over time.

Pride and Prejudice (2005)

A man and a woman with their foreheads touching, holding hands in a field during sunset.
©Image: OpenAI

Joe Wright’s Pride and Prejudice, starring Keira Knightley and Matthew Macfadyen, is a visually lush adaptation of Jane Austen’s classic novel. The chemistry is electric, the glances say more than the dialogue, and the unspoken yearning and tension will have you holding your breath.

It’s a film that invites reflection on how first impressions, ego, and class (in every sense) can cloud connections. After watching, you and your partner might end up talking about how you’ve changed each other for the better.

Lifestyle ethical clothing, sustainability, Tentree

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About TMM Staff

The Modest Man staff writers are experts in men's lifestyle who love teaching guys how to live their best lives.

If an article is published under TMM Staff, that means multiple writers worked on it. For example, sometimes several of us have experience with a certain brand, so we collaborate to publish a more thorough review.

Or, if an article was originally written by one person, but then it was updated by someone else, we'll re-publish it under TMM Staff.

Remember: all of our articles (including those below) are written by real people with decades of combined experience in men's fashion and lifestyle topics.

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