Sideways: A classic study in Dating and Beliefs



I am big a fan of using movies as a teaching tool.  A motion picture can really capture the non-verbal aspects of human interaction & communication so much better than any amount of written text could ever hope of doing.

There are a long list of movies/scenes relevant to dating that I usually recommend to guys seeking dating advice.  Today’s pick is “Sideways,” starring Paul Giamatti and Thomas Hayden Church.

What makes Sideways a great study is the depiction of two extreme archetypes and their belief systems regarding themselves, and their environment.  One aspect of what makes Sideways an interesting film is its character-study.  It can almost be likened to William Golding’s “Lord of the Flies,” one of my personal favorite novels.  In that Novel, conflict emanated from two polar opposites in the characters Jack and Ralph.  The former stood for the uninhibited self-indulgence and the latter represented what we’d call humane and conscionable sensibilities.    Freud would call it the “Id” and the “Super ego” which somewhat represents a similar dynamic, but then again, Freud was also supremely full of shit in a lot of cases.  Nevertheless, the conflict grows of the diametrically opposed characters.


Let’s get to the characters in the film:

Paul Giamatti plays Miles.


Clearly, an intellectual, Miles is also neurotic and unsure of himself. Too conscious of what others think of him, too unsure of himself and his own abilities, and sometimes too sensitive for his own good.  Having suffered through a terrible divorce, he is uncertain about himself and fears change in his relationship status.  He also is suffering through some sort of a depression, which he is currently taking medication for.  Miles is still mourning over his divorce, but yet, you get the impression that his marriage wasn’t that great to begin with either.  It’s a case of he being more afraid of his change to being single than remaining in a dreadful marriage.

Thomas Hayden Church plays Jack.

Basically, Jack is the opposite of Miles.  While not dumb, he is also not a bright individual.  Probably possesses an average IQ, and has an average sense of humor.  What he has going for himself is the unwavering belief in himself.  He is what many dating-coaches call a natural.  Part of that “Natural” disposition comes from not giving a fuck about anything. He seems to relishes in a bit of self-indulgence.  He is not particularly sophisticated, nor interesting as a person, but he is charming on some level.

I have met both of these archetypes in real life, but the fact of the matter is that most people fall somewhere in between these two characters, or perhaps it’s more accurate to state that most people possess personality elements from these two characters. The real question is: How much?

In essence, here is the predisposition of the two main characters:

  • Miles: Constantly looking for the negative, looking for any excuse to bail out.  Looking for any reason to find why something wouldn’t work out.
  • Jack: A unique ability to look at everything in a positive light.  Believes in his abilities almost to a delusional level.  Does not think a lot. He does things and then moves on.

Much of the dialogue between the two revolves around this very dynamic.  The first great display of this is at dinner where Miles comes across a waitress named “Maya” played by Virginia Madsen (who still comes across as sexy even in her 40s..).  Notice how she throws every sign that she is interested, and has been for sometime.  All of which Miles dismisses as a “Waitress looking for tips.”



One of the most significant moments in the film takes places at the get-together after dinner at the house.  We find our double-dating foursome back at the house where Maya and Miles are spending “Alone-time” chatting in the back porch.  This is one of those scenes that will make you cringe more than watching any of the gruesome and mediocre “Saw” movies.

At this stage, you’ll note that Maya is doing all the leading in the interaction, which of course, is usually the man’s job.  And yet despite this role reversal, Miles is still hanging in there and has not lost Maya’s interest.  Maya pretty much does everything she can to seduce Miles, except yell out, “Please Fuck me!  Fuck me now!”     Pay close attention to her as she is giving her speech about wine evolving which ends with her blurting out, “And it tastes so fucking good.”   (That is 59:22 in the movie, brilliant acting, very well written dialogue)

This is the moment where Miles ought to be picking her up and carrying her somewhere for a physical onslaught of unbridled passionate sex, the type of sex where clothes are torn off the body.

Instead, there is that uncomfortable pause that makes us cringe.  Part of this is perhaps due to the fact that Miles is not only uncomfortable with himself emotionally, but he is also uncomfortable with himself sexually.

This, of course, leads to the demise of their charged interaction.  This is where the screenwriters got it right.  It is a strange phenomenon that you’ll observe:  When a woman is ready “to be taken” and the man cowers away, she loses respect for him even if it’s on a subconscious level.  It’s not a pretty sight, and while you’re cringing, you do feel pretty bad for Miles.

Jack, on the other hand, doesn’t seem to even be the least bit bothered than he has a wedding to attend in less than a week, where he happens to be the groom.  He is on a trip for his final hurrah as an engaged man on ass hunt.  On the trip, he has sex with the Asian bartender whom he suddenly wants to move in with.  He considers postponing the wedding, but then continues with it, once his new fling falls apart.

A few days later, he has sex with a rather chubby married waitress working in a roadside café.  This is another mark of guys who are proverbial players: They’re not concerned with necessarily scoring “Hot Women.”  They sleep with a lot of women, some are attractive, and some may be chunky roadside waitresses.  It’s rather irrelevant.   While, billed as his last hurrah, one can’t possibly be under any illusion that he’ll remain faithful once he is married.  Let’s face it: He probably won’t even last 3 months.  This, he refers to as his plight.

While neither character could serve as a role model, there are things to be learned from “Sideways.”



Some of the lessons to be learned from “Sideways” as a visual literary work:

These two characters effectively display a vastly different belief system.  It’s their beliefs regarding themselves, each other, dating, and what is possible that fascinates us.  If you’ve seen this film before, you ought to watch it again. This time, pay close attention to Jack’s facial expressions.  Jack wouldn’t be categorized as a funny guy.  In fact, many of his jokes are rather cheesy. Yet, he is able to pull it off on some level because he believes in himself. More importantly to note, he is very comfortable with himself, even with his cheesy jokes, (such as his growl at the end of dinner.)  It’s this self-comfort that enables him to move forward with ease.

Most important of all, perhaps, is Jack’s “Fire and Forget” ability.  He is able to take a shot at something, and he is able to let go if he does not achieve his desired result.  If he approaches a woman and she turns him down, he is able to let that go and move to the next one.  In fact, you could well imagine that his reply probably would be, “Dude, that was 5 min ago.  Why are you still talking about her?  There is a new girl over there.”

If you have a bad night approaching girls recently, maybe you owe it to yourself to a pop in a copy of the Sideways DVD as a reminder, a reminder to not be like Miles, a reminder to have that “Fire and Forget” ability like Jack.  Then again, maybe you were dating someone who no longer is interested in seeing you.  We’ve all been through it.  To put it profoundly, it sucks!  Watch Sideways, and minimize your dwelling, and Maximize your opportunities in connecting with someone who would LIKE to see you.  Maybe you’re a woman reading this right now.  It’s the same for everyone.  Miles shows what looking in the rear view mirror gets ya: Melancholy feelings reminiscing about what was, instead of what can be in the future.

This is the toughest part of dating to master.  You can learn all sorts of techniques and tactics, but getting over the voices and bullshit in our own head is one of the keys to mastery.  It sounds simple, but takes work to accomplish.   The term “Inner-game” can be ambiguous.  What the fuck does that mean?   Jack is able to quantify it for us.  He is able to give it a shape and form, a visual representation which can serve as a model to emulate.

Most men who seek dating advice tend to dwell on perceived failures.  They tend to relive interactions and figure out what they could have done differently.  Part of this is the way men are taught dating: The Focus is on sets and trying to get every girl you approach.  They’ll tell you, “Maybe you should have Negged, Cocky/funnied, or conducted an action described by a three letter acronym.”   This dwelling translates into various walks of life: In sports, an athlete may dwell on a shot he missed, and in a professional setting, a salesman may dwell and reflect on a sales opportunity he missed.  It goes on and on and on……

Sometimes, you need to have Jack’s attitude:

“Dude, that was like an hour ago. Why are you still talking about it???”


PS.  The articles on this blog will have a profound impact on your dating life.  Please realize that they are supplementary and supporting material to what I discuss in my expanded work.  Get a copy of my Ebook here: Building Attraction with Women