I was thinking the other day some of my greatest date night movies. First off, as all of you know, I think going on a movie date in the first couple of dates is not a great idea. Why?

You don’t really know the person yet. So you end up picking them up for a movie, sitting there in silence, and wondering what they’re thinking about. I remember the first time I ever went on a date night movie. It was hilarious.I was in high school at the time.  I remember all I was thinking about was:

When do I make the move?  When do I grab her hand?  When do I kiss her?  Do we make out in the movie?  

All things that young, high school kids think about.  Do you guys remember the movie Diner, where ‘Boogie’ (played by Mickey Rourke) actually put his dick inside the popcorn? And his date reached down for popcorn and grabbed his dick? Then Rourke had to explain to her that he got so excited just sitting next to her, his dick popped up through the box?! Hilarious.

I think movies and dating have been made fun of for so long. Back in the olden days, in the 50s and the 60s, there used to be drive-in movie theaters. You would actually drive up to a post, put this speaker box inside of your car, and that was how you heard the movie. Though nobody really cared about the sound. Drive-ins were all about the extracurricular stuff going on in the car

Movies and dating have been synonymous for years.  Once again, until you really get to know somebody and you’re comfortable sitting in silence, I think movies and dating should be avoided. At least for the first few dates. But let’s just say you’ve met somebody.  She’s hot, she’s great, she’s sexy, and you like to watch movies with her.

I think it would be really awesome to be able just to sit back and relax and watch movies together at home.  Movie dates with someone you know a little bit are a lot of fun.  You can talk, you can hang out, and you can get on the couch and touch. So here are some of my best date night movies:


You’ve Got Mail

Sleepless in Seattle

Jerry McGuire

Nine and a Half Weeks

The Notebook

Crazy Stupid Love

50 First Dates

Three Kings

Midnight in Paris

Match Point

Vicky Christina Barcelona

No Way Out

The Graduate

Eyes Wide Shut

On a Golden Pond

Wedding Crashers


(Who could forget the scene when he hits on the girl at the bar, and then he calls her 14 times in a row).


Dirty Samson


Annie Hall

There are many others that I can put on this list. There are many dramas and thrillers that could be a lot of fun too.  But these were some of the movies that we talked about when we did our recent boot camp (a couple of the guys had questions about dating and movies).

My favorite date night / movie night is all about coming over, curling up on the sofa, making a little dinner, watching a movie, and snuggling.  Of course this is when you’re already comfortable together.  You can always go to the movies, but you need to wait until you build up a little intimacy, a little trust between the two of you.

You need to be comfortable sitting in silence. When I bring myself back to that 15 year-old guy, I don’t remember a single movie I saw on a date in high school. And I went on many movie dates, because I would sit there the whole time thinking:

What is she thinking?  Does she like me?  

And let’s face it; a lot of us have the same boyhood thoughts in our brains.  Please, write down your favorite date night movies and why and put it in a post. Enjoy.