The Top 10 Movies Every Young Man Should Watch Before Dating

There’s a lot to learn before a young man enters the world of dating.  Here are the top 10 movies that have lessons that will educate him, help him, and get him ready to navigate the difficult world of dating.  Let’s start with number 10:


10. Starship Troopers

What? Did you expect The Notebook?  This movie about an alien invasion and battles between humans and bugs is nominally based on Robert A. Heinlein’s classic of the same name.

Why it’s important: The main character, Johnny Rico, is oblivious to Dizzy Flores, his fellow high school student.  She has a huge crush on him and eventually lands him by the oldest play in the book: proximity.  She sticks with him.  She’s at his side in the mud and blood of battle and when it comes time for him to decide between her and the gorgeous Carmen, his original love interest is far away and way out of the picture.  This is a movie with many flaws, but the singleminded pursuit of Rico by Dizzy Flores is worth examination.  Plus, of course, the battle scenes are epic.

9. 50 First Dates

This charmer starring Adam Sandler and Drew Barrymore is about a girl who is seriously injured in a car crash and ends up with permanent short-term memory loss.  Adam Sandler falls in love with her even though she can’t remember him when she wakes up each morning.

Why it’s important: The movie is a comedy about a very serious aspect of love.  To love someone with a disability means to accommodate them, and what Sandler’s character does to win and to keep her love is the kind of quiet heroism that seldom gets screen time.  Drew’s character could have cancer, or be in a wheelchair, or be stricken with any kind of disease.  The story is about how you overcome those obstacles and still make love work.  Powerful stuff for a movie that’s also a hilarious comedy.


8. Independence Day

The epic space-alien invasion movie includes iconic scenes of worldwide monuments being destroyed, among them the White House, the Chrysler Building, and most of Los Angeles.  Humans must battle for their very existence against a better-equipped and ruthless enemy.

Why it’s important: Scientist David Levinson (Jeff Goldblum) and hotshot pilot Steven Hiller (Will Smith) represent two beautifully told arcs of romantic love. David’s wife has left him for a high-powered career in the White House and pilot Steven is in love with a stripper who will destroy his chances for a career at NASA if he marries her.  Making love and careers work together isn’t easy, even if you’re not in the middle of an alien invasion. Watching these couples make it work is as much fun as seeing America put on combat boots and stomp an enemy into the dirt.

7. Scott Pilgrim Vs. The World

This amusing tale of a young man who must fight each and every one of his girlfriend’s evil exes is set up like a video game, complete with flashing lights and an onscreen score.

Why it’s important: Michael Cera doesn’t cut a heroic, romantic figure as Scott Pilgrim, but his determination and intelligence make the movie work.  He simply can’t defeat these “evil exes” but somehow he does, in a cartoonish yet endearing fashion.  Learning how to live with a romantic partner’s past is crucial, and getting beyond a past relationship can be a battle.  Sometimes it’s a battle worth making.


6. Groundhog Day

Bill Murray stars in this classic film about a man stuck in a time loop where he wakes up each day in the exact same time and place.  The day is Groundhog Day, and he must find a way to live the perfect day to break out of the loop.

Why it’s important: Murray’s character, Phil, has the hots for fellow newscaster Rita, played by an incandescently beautiful Andie MacDowell.  He doesn’t care about her at all, he just wants to collect the trophy of sleeping with her.  Eventually, as he is forced to live the same day again and again, he falls in love with the real girl behind the beautiful face. His genuine love for her wins her heart and breaks his curse.

5. Mr. & Mrs. Smith

The sizzling chemistry between Brad Pitt and Angelina Jolie lights up the screen in this tale of two spies who fall in love and get married, all without telling each other what they really do.  When a hit is put out on each other, with each other, their secrets come out and they have to deal with the result.

Why it’s important: This movie is a lot of fun to watch and the romance is well told, but the reason it’s important is the idea that a fundamental secret destroys a marriage.  These two aren’t honest with each other, and although they love each other at first the secrets between them start to destroy them.  When they’re honest with each other, they are unstoppable and unstoppably in love.


4. Hitch

Will Smith plays the title role of a matchmaker who helps men learn how to date women.   When he meets a beautiful, intelligent gossip columnist he forgets every rule and makes every mistake trying to win her heart.

Why it’s important: Watching a suave know-it-all fall on his face is as fun as watching him manage to get the girl of his dreams after all, but the real lesson of this movie is how Hitch’s matchmaking works and how simple his lessons are. To listen, to be kind, to be restrained — these are gentlemanly values that are seldom taught to our young men anymore.  The movie is a slick Hollywood package that beats with a very old-fashioned heart.

3. Deuce Bigalow: Male Gigolo

Rob Schneider stars in the title role as a small-time aquarium cleaner.  When he accidentally breaks a vacationing gigolo’s expensive aquarium while cleaning it, he decides to take on the gigolo’s role in order to earn money to replace it.  He’s timid, he’s awkward, and every client he encounters is a woman who couldn’t find a man any other way.  He encounters the elderly, obese, and disabled, and in his attempts to do his job he discovers the love of his life.  He has to overcome his own ideal of the perfect woman in order to find happiness with a disabled girl whose friends bought her a night with a gigolo.


Why it’s important: Deuce Bigalow is a raunchy movie with a heart of gold.  Rob Schneider plays an obnoxious, unattractive man, but he earnestly tries to please the women he’s sent to service.  Instead of giving them meaningless sex, he discovers what fills their lonely hearts and he provides them with the affection they desperately need.  Although he does this inadvertently at first in an attempt to avoid sex with these unattractive women, he grows to understand what love is really all about.  Deuce finds happiness and love because he comes to understand that these unattainable objects called women are people after all.

2. Shallow Hal

Shallow Hal stars Jack Black as a pompous, self-absorbed man who will only date beautiful women.  The trouble is, he’s a jerk and the women he desires are out of his league.  When Hal is hypnotized in an elevator by self-help guru Tony Robbins, he (and we) can suddenly only see the inner beauty of women.  He falls in love with an obese girl, but all we see is the lovely Gwyneth Paltrow.

Why it’s important:  When Hal sees inner beauty, his life is turned around.  He falls in love with a gorgeous woman and she falls in love with him.  Her handsome friends (who are actually unattractive and nerdy) accept him and bring him into their world.  An ugly, shriveled nurse that Hal encounters during the movie is actually a gorgeous supermodel, but her interior is what Hal sees, and she disgusts him.  She’s hideous because her personality is stunted and mean. Hal entertains a children’s burn ward full of disfigured children and never flinches when he hugs them because to him they are perfect.  Hal becomes the man he’s meant to be, and finds happiness, because he stops being shallow and becomes just Hal.


1. The Enchanted Cottage

This movie is set in 1945, directly after World War II.  A scarred, disfigured soldier travels to the vacation cottage where he was supposed to spend his honeymoon.  He broke the engagement after his horrific injuries.  He meets the homely, shy maid who works at the cottage and they fall in love and get married.  That’s it.  That’s the whole story.

Why It’s Important:  This is a brilliant and subtle film, starring Robert Young and Dorothy McGuire, and it’s also in black and white, filmed in 1945, and exhibits the slow, talky dialogue of the time.  Fat chance a young man will sit still for this one, and that’s a shame.  The genius of this movie is how two unattractive people begin to transform into beautiful people right before our eyes.  As they fall in love, the scars disappear. Their lumpy features smooth into beauty.  When they kiss near the end of the movie you see two gorgeous movie stars, and in a glimpse in a mirror you see the reality of scarred flesh and unattractive features.  The truth in the mirror doesn’t matter.  What they see is what matters, and they see nothing but beauty.

If a young man watches these movies and absorbs their lessons, he’ll enter a dating world full of beautiful women who are fascinating, kind, and brimming with energy and intelligence.  There really is a world of interesting girls to date out there.  In the end, he’ll marry a movie star.  And to her, he’ll be one too.



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