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Our Favorite Movies For Date Night

In-home date nights are some of our favorites…

…and some evenings we just want to cuddle up after a long day of work, share some popcorn, and watch a movie. We decided to put together our favorite date night movies of all time and even included a connecting question to ask each other after you’ve watched the movie to help you connect emotionally.

The Story Of Us

By far the BEST movie ever made about marriage. This movie is real and even painfully emotional in many scenes, but the actors do an incredible job of portraying a married couple who are separated and have to decide if they should stay together or end their marriage of 15 years. This couple endures in-law issues, intimacy issues, a lack of perspective-taking and fights over the same things over and over again! Have the tissues handy!

Connecting Question: What are some ways we can make sure we hear and respect each other’s perspective?

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Couples Retreat

This movie is about four couples who settle into a tropical-island resort for a vacation. While one of the couples is there to work on their marriage, the others fail to realize that participation in the resort’s therapy sessions is not optional. This film reminds you that all couples are unique and that you can either focus on your differences or focus on what you have in common.

Connecting Question: What are some of our differences and how do they balance us out?

The Family Man

In the film, a single investment broker who loves his independence and lifestyle gets an opportunity to see how his life would’ve been if he got married and had kids. After a bad start, day by day he’s more confident in his new life and starts to see what he’s been missing. Turns out money’s good to have but it’s not everything.

Connecting Question: Do you ever find yourself comparing your life with others who have more money, more time, and more independence?

Just Married

In this film, a newlywed couple honeymoon in Europe, where obstacles challenge their ability to sustain the marriage. While the movie is a bit corny, the storyline is powerful in many ways because oftentimes, newlywed couples enter into marriage expecting things to be great for the majority of the time. Then life happens, adulting becomes more challenging and you get to choose to embrace the mundane parts of marriage, or not.

Connecting Question: When we were engaged, what were some expectations you had about marriage and what you thought it was going to be like?

Date Night

We’re both huge fans of Steve Carell and Tina Fey so we knew we’d love this movie no matter what. They play a married couple who are worried they’ve lost their spark. A case of mistaken identity turns this bored married couple into something more thrilling and even dangerous. Definitely not your typical date night experience but this is hilarious and very entertaining.

Connecting Question: How can we make our date nights together more exciting?

When Harry Met Sally

An oldie but a goodie in so many ways. This movie reminds you of how important it is to be friends with your spouse. If you haven’t seen it, we don’t want to give away the ending but some of our favorite scenes are when they interview the different couples who share their love story on the couch.

Connecting Question: In what ways can we continue to build our friendship and connection?


To be completely transparent, we’re not huge fans of this movie but we do love the life lesson, so it made our list, and here’s why. The acting is cheesy, some of the transitions are awkward, but it sends a great message of why love is a choice, not a feeling. This couple is heading towards divorce (just like we were) and the wife has given up. The husband is challenged to try one last time… for 40 days!

Connecting Question: What are some practical ways I can show you that I love you?


A workaholic husband and father of two, who seems to have it all, finds a universal remote that allows him to fast forward and rewind different parts of his life. Complications arise when the remote starts to overrule his choices. A fantastic reminder that living on auto-pilot isn’t really living at all and that at some point it’s best to embrace the mundane.

Connecting Question: What are some ways we can make sure we never put our marriage on auto-pilot? How can we be more intentional with our time together?

Written by Meygan Caston

Meygan Caston is the co-founder of Marriage365 and lives in sunny Southern California with her husband Casey, their two children and dog Hobie. She loves her family, the beach, writing, spa days and helping couples connect in their marriage. Her life long dream is to live with the Amish for a month, walk the Camino and have lunch with Brené Brown.

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