5 “Must Watch” Movies For Guys Going Through A Break Up

In the days or weeks right after breaking up, talking it out with friends sometimes just doesn’t do it justice…

The whole avalanche of emotions, all the inner conflicts and complexities…

Trying to express that to a friend can just seem almost impossible if you aren’t a poet, a writer or someone who just isn’t used to dealing with something as overwhelming as a broken heart…

And sometimes you’re just so exhausted by the whole thing to have the mental horsepower left to try articulate it.

Although talking about your break up with your friends is really important, there is another way to “get it off your chest” so to speak.

I call it “movie therapy.”

The idea here is that you watch well written, well acted movies about guys going through the same thing (or similar) that you are.

When you watch a movie that really speaks to where you are at, especially while you in the thick of things, it helps you process it much faster, while giving you a different perspective on your situation.

You get that same purging effect that you would get if you talked out with a friend, except that you are watching somebody go through it.

And if it’s a good movie, it will show all of these the little subtleties that you would only understand if you went through something similar yourself.

The trick to this is to find a few of these good movies and make a night out of it.

Spread a few movie nights across a couple of weeks, and keep the movie sitting next to your TV for those weekday or weekend nights that you find yourself alone.

When you have a few of these nights and you really get into these movies you’ll notice a few things.

  • As isolating as what you are going through might feel, even some of the most embarrassing situations are very universal.
  • Many of us guys really do have trouble getting through painful break ups, despite the sterotype that we’re just supposed to shake this stuff off and move on.
  • There are many very profound lessons you can learn by watching how these characters handle their situations.

In the Land of Women:

This movie is great because it really zooms in on a couple of those painful moments that any guy has to go through when a girl leaves him.

Carter, a softcore porn writer, gets dumped by his girlfriend and tries to get over the relationship by retreating to live with his senile grandmother while he tries to finish a novel he’s been working on for years.

Scenes to watch for:

The intro scene when his girlfriend sits him down and breaks up with him is very painful to watch, as she pretty much gets up and walks away right as he is begging her to stay and explain why she’s leaving.

Also about a third way through the movie there is a brilliant scene where Carter has a “love attack” and calls his ex, only to hear her at this party laughing and flirting with other guys and ultimately getting cut off before he could finally say what clearly had been on his mind the last few days.


Girl’s explanation for things often don’t make any sense.

Don’t ever call your ex when you’re in the middle of a love attack.

High Fidelity:

This movie manages to be painful and entertaining to watch because the main character really embodies the whole neurotic mind-racing-at-turbo-speed trying to make sense of everything feeling you get right after things go bad.

Rob, a record store owner, get dumped by yet another girlfriend and begins to review why all of his previous relationships went bad.

Scenes to watch for:

Many of the character rants into the camera are pretty funny, but favorite is when he is in bed and he can’t get the image of his ex girlfriend having sex with another guy out of his mind.


Yes, even guys can get pretty neurotic when they’ve just been dumped.

Painful imagry of your ex with another guy is something guys seem to really torture themselves with.

Conversations with Other Women:

This movie is good to watch because although its mostly a conversation between two people, it is done in split screen-and often in the opposite screen there will be scenes from the couples past that shed light on things they are saying to each other now.

A man and a women meet each other at a wedding and at first it seems like they are just flirting with each other, but as it turns out they have a past together that neither of them have moved on from.

Scenes to watch for:

There is great scene where the two of them allude to the time right after they first separated, and in the split screen it shows the man when he was much younger tapping various girls on the shoulder on the street because from behind they look like his ex girlfriend. Brilliant stuff.


If you’ve had the whole experience of seeing girls that look like your ex girlfriend everywhere you’ll love that scene.

If you’ve fantasized about the idea of having a fresh start with your ex, this movie toys with that idea.

The Break Up

This movie manages to be really funny and also stay true to reality at the same time. I like it particularly because it does not follow the typical Hollywood happy ending formula.

Basically the movie starts with the break up and shows all the different stuff that goes down between the Vince Vaughn’s character and Jeniffer Anistons character. All the drama of still living together while broken up, divvying up the friends and dating others to make each other jealous is all there.

Scenes to watch for:

While the whole movie is pretty good, my favorite scene is when Vince’s last attempt to get her back doesn’t work.

What’s great about this scene is how he handles it.

No crying, no begging…But no holding back either.

In this scene you really see the distinction between being vulnerable and being weak…

After she turns him down, heartbroken and upset, he walks away without losing his composure.


If you have told your ex girlfriend how you feel and she still didn’t come back to you, its time to walk away.

If you can, watch this movie with a female friend. The two of you will see two different movies, because what is clearly Jennifer’s character being a total psycho, may very well make total sense to her. It’s weird.


There is no way I can leave this one out. This movie has been the quintiseential break up movie for guys now for almost a decade, and although its pretty famous for that already, it still has to be mentioned. The way the movie portrays the lingering pain after a break up and shows all the pitfalls and screw ups the main character goes through on the way to finally getting over her.

Mike, a guy who left his girl in New York when he came to LA to be a star. It’s been six months since his girlfriend left him and he’s not doing so good. So, his pal and some other friends try and get him back in the social scene and forget about his 6 year relationship.

Scenes to watch for for.

A brilliant scene is the when Mike (Jon Favreau) and Trent (Vince Vaughn)s bring a couple of girls back to their trailer and Mike pretty much ruins the whole vibe by talking about his ex girlfriend.

Also the scene where Mike finally gets the courage to approach another girl and ends up calling her that same night and screws up the whole thing because he’s still to self conscious and needy.

The ending scene when we see Mike finally choose to not thke the call he had been waiting for so deperatly from his ex girlfriend.


Being that guy who keeps talking about his ex girlfriend can really bring everyone else around you down.

The void you feel right after a break up and the desperation to fill it ironically screws up your chances of meeting other women.

There will come a point, where you consciously make the decision that you are going to do whatever it takes and resist whatever temptations so you can move on.