6 Great Date Movies That You Haven't Thought Of Yet

It’s been a couple of years since I suggested some great movies to watch with a woman, so I figured an update was long overdue.

Let’s face it.  While “dinner and a movie” is a flat-out terrible idea for a first date, that doesn’t mean that either having dinner OR watching movies is something that should NEVER happen when with a woman.

In mean, as far as dinner goes I’ve literally written the book on how absolutely GOLDEN it is to cook for your date.

And similarly, watching a movie together at either your place or hers can be a GREAT WAY to “break the ice” when it comes to getting close physically.

So then, yeah.  Knowing that much about the strategic importance of actually watching said movie together, the other major question then becomes WHICH movie to watch.

When it comes to selecting a great date movie, the basics are pretty simple.

First, you DON’T want one that’s either TOO much of a “guy” movie OR a “chick flick”, although erring on the side of the latter is preferable to the former.  The key is to make it a movie you’re both likely to enjoy…together.

Along those same lines, you’ve got to be sure to pick a movie that’s not a total downer.  You don’t want the whole remainder of your evening ruined by haunting thoughts long after it’s the credits roll.   For example, you’d want to avoid movies like The Green Mile or Full Metal Jacket.

Ideally, you want to also choose a movie that will put her in a frisky mood, of course.

The best movies to serve that purpose are the ones that feature a “boy meets girl” story between attractive characters that not only ends well, but has some sensuous (if not overtly sexual) moments sprinkled in there for good measure.

In addition to the basic qualifiers for a solid date movie, there are also a couple of “advanced” advantages afforded by particularly good choices.

Does the storyline provoke really good discussion about the nature of male/female relationships in general?  If so, that’s great.

Further, if the movie has a key scene or two that absolutely DEMANDS some sort of commentary about what’s happening onscreen, that can be a GREAT way to “test” her character a bit.

For example, let’s say she’s openly appalled by Rosie Perez’s character’s attitude in “It Could Happen To You”.  That would be a good thing.

So enough already.  It’s time to recommend some movies around here.

Now, just like last time when I mentioned movies like Serendipity, Garden State and Heart And Souls I’m going to bypass the flicks that EVERYONE has long since filed away in the “date movie” column (e.g. Jerry Maguire, Bull Durham) and give you some really good (and relatively recent) ones that neither of you may have caught yet.

Here goes (in no particular order):

1)       My Girlfriend’s Boyfriend

This movie was released last year, and almost nobody saw it in the theatres.

Fair warning, there’s something inherently wrong with the “flow” of this movie relative to it’s surprise ending.  You both may be left scratching your head a bit.

But that aside, the baseline premise of a “good girl” (played by Alyssa Milano, which is nice) confronted with dating two “good guys” at the same time makes for a brilliant, brilliant date movie.

The particular genius of this film lies in it’s subtle implication that having a lot of money, a nice car, etc. isn’t always what “gets the girl” in the end.

In fact, you’ll really like how this movie acquits the premise that you don’t exactly have to be “Mr. Perfect” to succeed with women.

Great relationship discussion material abounds here, and yes…she’ll want to be kissed after it’s over.  Possibly before.

2)       The Ugly Truth

My bias shows here, as one of the central characters in this 2009 movie is a dating coach.

Nevertheless, the simple fact that said dating coach and the inherently adorable Katherine Heigl start off at complete odds with each other over stuff related to raw masculinity vs. feminism alone makes this one worthwhile.

But you just KNOW that Katherine Heigl is, as usual, ALL WOMAN ALL THE TIME somewhere under there.

Ultimately, this could end up being your favorite “romantic comedy” of all time.

And if it’s one of hers also, you’ve got a great woman on your hands (and probably in your arms).

3)       Up In The Air

This movie came out in 2009, and is about a guy (played by George Clooney) who’s on a quest to get ten million frequent flier miles.

Vera Farmiga plays George Clooney’s love interest, and she’s one of those women who might not knock your socks off at first but who starts seeming hotter and hotter as the movie progresses.

That’s perfect, as far as date movies go.  It keeps the focus on what’s happening on screen versus on whether or not you think the girl in the movie is hotter than the woman your with, etc.

The scene where the two of them meet each other is pretty hot stuff…and a great example of how to cold-approach a woman.  The two of you should enjoy that, along with the various and sundry trysts and turns that follow.

Later, however, the shocker of an ending will end up giving you some insight into how your main squeeze views relationships…guaranteed.

It’s a good movie overall, and Clooney’s character is—as usual—an effective case study of how to be masculine and effective with women.

4)       My Last Five Girlfriends

This is a fairly obscure British film, but quite possibly one of the greatest date movies ever.

I mean, the movie is essentially a retrospective into the main character’s last five relationships with women…each of whom has a COMPLETELY different personality and general outlook on things.

That’s all you really need to know.  How can you go wrong?

Added plusses are it’s actually pretty hilarious and entertaining throughout.

5)       The Social Network

This one is probably the “sleeper” of the list.

After all, since this film is supposedly a somewhat fictionalized representation of the story of how Facebook got started it’s easy to dismiss it as “geek fodder”.

But when you actually watch the thing, you see real quickly that the movie is actually mostly about relationships—including male/female ones.

There’s a fantastic contrast between different types of personalities, of varying degrees of sexual attractiveness and personal power—with those factors not always aligned as expected.

The end result is a truly fantastic drama, like unto which should keep any woman on the edge of her seat.  You should have a great time with your gal disagreeing over Justin Timberlake.

Besides, above and beyond any other reason to choose this movie, women dig Facebook, right?  No kidding.

An added “bonus” here, by the way, is that Rashida Jones is in the movie.  If you’ve seen “I Love You, Man” (which could get “honorable mention” in its own right as a solid date movie) she plays the main dude’s fiancée.

6)       Grown Ups

This movie is pretty new to DVD, and although a lot of people have seen it already it still earned a place on this list.

That’s because I can’t personally remember a movie that was a more perfect hybrid of “guy movie” and “chick flick”.  (But if there is one out there, it probably has Adam Sandler in it is also).

The cast is great, the male/female dynamics fly at you with greater velocity than a Tim Lincecum fastball, and it’s legitimately a funny movie.

To sum it up, both of you will enjoy the movie and probably be ready for a good, solid make-out session by the time it’s over.  Life is good.

OK, so there you have it.   A half-dozen date movies you can start diving into immediately.

Note that I let you know which movies were available via “Instant Play” on Netflix.  That’s always a major convenience for those of you who have a Roku box…which you definitely should.

Just for good measure, let me give you one other “off the board” pick as far as great date movies go:  Giant.

This one is from way back in 1959, so it’s specifically for old movie buffs.  But it’s one of the late Elizabeth Taylor’s best efforts and one of the few flicks that James Dean actually starred in.

The relationship between Rock Hudson’s character and Liz’s is epic, and you’ve got to love Jett Rink (James Dean).

One caveat, however.  You’ll want to pay attention to the fact that he length of the movie is a staggering three hours and twenty-one minutes.

So if you believe that “more is better” when it comes to getting close to your girl and letting things “warm up”, then Giant should give you all the time you need.

Just make sure neither of you have to get up and go to work in the morning.