Ten Movies to Make Your First Date Unforgettable


Women renting moviesBy Kim Baker

While the phrase “Netflix and chill,” may be, in some communities, a metaphor for more than movie watching, sometimes you really do want to share a first date over a great film. As the temperature outside becomes crisper, there is nothing more romantic than curling up on a first date with a good movie, a glass of wine, and popcorn. Movies are a great opportunity to raise conversation topics that allow you to get to know each other.


Here I offer ten movies options to make that first date unforgettable.

1. Bridesmaids

Why you should see it: This classic comedy, with a myriad of talented cast members, can offer you the chance for hearty laughter on your date, which automatically lightens the first date jitters. Studies have shown that laughter creates a lasting bond between people.

Women laughing at movie

2. Crazy Stupid Love

Why you should see it: Ryan Gosling and Steve Carell pair in this film, as mentor and mentee, where Carell’s character tries to get back his lost swagger. Most of us can identify this search for swagger and the film opens the opportunity to share experiences around a time you each had to find your swagger.

3. Better Than Chocolate

Why you should see it: This lesbian classic offers a sweet lesbian love story that takes place when it wasn’t okay to be a lesbian, offering conversation opportunities around coming out, dealing with family, and even sex. These issues are crucial in identifying compatibility.

4. The Postman

Why you should see it: Starring Kevin Costner (back when he had hair), this post-apocalyptic drama will generate discussion later about values and integrity during challenging times and offers entry points in talking about war, weapons, and basic good versus evil.

5. Love Actually

Why you should see it: This classic Christmas film offers heart felt love in all forms and witty humor that will have you holding hands at the funny, sweet parts. An added bonus - the opening scene of the movie will have a long lasting effect on you whenever you find yourself in an airport.

6. Rent

Why you should see it: Whether you’re a fan of musicals or not, this heartfelt remake that includes some of the original Broadway cast will have you laughing at the witty dialogue, and crying at the loss of so many in our community, while opening the door for dialogue around AIDS, the socioeconomic divide, and the way friendship withstands the test of time.

7. Groundhog Day

Why you should see it: The best part of this classic Bill Murray film is that it is comprised of more than funny one liners – it has heart. In the way that only the best movies of all time can do, Groundhog Day lets you imagine yourself reliving a day in your life and evaluating what you would learn about yourself, as Murray’s character does.

8. If These Walls Could Talk Part 2

Why you should see it: Originally an HBO movie with a fabulous cast including Ellen DeGeneres and Sharon Stone, this film offers three sweet, realistic stories about what it’s like to be a woman who loves women. One poignant moment is when an elderly woman, who has lived a closeted life with her long-time partner in the 60’s, passes away and her family forces her partner to move out of their house even though she’d been paying half of the mortgage. This realistic scenario, even today in many states, can open up discussion around important topics like money, financial planning, and dreams for the future.

9. Hitch

Why you should see it: Will Smith stars as dating coach Hitch in this hilarious comedy where the audience watches as Hitch (Smith), who is normally all smooth and swagger suddenly becomes a complete disaster around his love interest, played by Eva Mendes. Aside from some hilarious scenes, including one where Hitch coaches a client on how not to dance, the film offers a real look at how we can get in our own way when it comes to dating – a great topic to discuss afterwards. Plus, you can have the inevitable, “I’m not a good dancer,” conversation (if you need to).

10. The Proposal

Why you should see it: In this classic romantic comedy starring Sandra Bullock and the other Ryan, Ryan Reynolds, you’ll experience the connection of family and watch as Bullock struggles with a work/life balance, excellent topics for getting to know your date. Also, the smart humor combined with realistic emotions make this film more than just a simple rom com.

First dates can be awkward. Showing up full of nerves and a virtual list of questions in your head can be about as fun as accidentally swallowing a fly. Movies are a great option for first dates because they allow some shared laughs and connecting throughout, along with opportunities to have some real conversations afterwards. The bonus is that you learn a lot about how compatible you are by the kind of movies you like, and how much talking you do or don’t do during the films. What better way to ease first date jitters that to laugh, talk, and connect?

For more online dating advice, check out our expert tips on lesbian dating.

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