20 Best Breakup Movies of All Time

By on December 9, 2014






You’ve had a bad break-up, or a good one, but a break-up is still a break-up – there are emotions to process and a new life to adjust to, especially if you’v been in a relationship for a long time. It can help to watch movies or read books to get you through this time as you get perspective and realize there is life beyond your break-up. By watching some of these movies you will get inspired to create the life of your dreams, go after what you want and, eventually, find love again.

The Break-Up – Because That’s Life

This is a movie where a couple breaks up, but since they own a condo together, they decide to be roommates for a while longer, which causes some awkward, hilarious and devastating situations as they try to make each other jealous and take out their hurt on one another.

I remember watching this after breaking up with my long-term boyfriend and was like “Yes, that’s kind of what it’s like.” Not that we owned a condo together or tried any of the schemes in this movie, but there are moments that are very true to what it can feel like being in a relationship and breaking up. It’s not the most happening movie, but it helped me feel OK about breaking up with my ex at the time.

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Bridget Jones’ Diary – A Good Laugh About Single Life

This is a classic – it’s funny and filled with all the terrifying situations you go through as single. Like getting drunk and singing “All By Myself,” cooking your date blue soup, talking to “smug married couples,” and falling for your boss. Not to mention having your bottom plastered all over national TV (talk about getting the wrong angle!).

There are few movies that have made me laugh more through the years than Bridget Jones, so if you are feeling down after a break-up and need a good laugh, but don’t mind some romantic love to perk you up – this is definitively a movie that should be on your watch list.

[answering phone]

Bridget: Bridget Jones, wanton sex goddess, with a very bad man between her thighs… Mum… Hi.

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He’s Just Not That Into You – Adjusting Your Dating Techniques Before Dating Again

Sometimes you are employing all the wrong dating techniques. Seriously. You are letting an impulse (or several) ruin your entire dating life and you don’t even know you are doing it, because it is such a strong impulse…to send five messages too many to that hot guy. But it does you no good. In fact, the hot guy will be creating his exit plan before he even entered. Instead you need to give him time to really work on his entry plan. Dating you should be a privilege, not something that’s handed to him on a silver plate. So watch this movie, because you deserve a guy who fights for you. And in the meantime you deserve some laughter.

Mary: I had this guy leave me a voice mail at work so I called him at home and then he e-mailed me to my Blackberry and so I texted to his cell and then he e-mailed me to my home account and the whole thing just got out of control. And I miss the days when you had one phone number and one answering machine and that one answering machine has one cassette tape and that one cassette tape either had a message from a guy or it didn’t. And now you just have to go around checking all these different portals just to get rejected by seven different technologies. It’s exhausting. 

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Under the Tuscan Sun – Healing a Broken Heart

This is a favorite movie of mine. Maybe because, like the protagonist, I’m a writer, maybe because I love the Mediterranean, or maybe simply because it’s the story of healing a broken heart and how it is possible. You just have to give it time and honor your own heart in the process – go do what it is you love doing. It’s a slow movie, but it’s cozy and filled with all the things that make the (or at least my) heart sing: home, sun, food, friends and love.

Frances: What are four walls, anyway? They are what they contain. The house protects the dreamer. Unthinkably good things can happen, even late in the game. It’s such a surprise.

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Legally Blonde – Laughter Mingled with Determination

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Yeah, I’m blonde. I have a blog called Confessions of a Dizzy Blonde and I may or may not have a few blonde things in common with the main character, but that’s not the point. The point is that this is a funny, lighthearted movie, yet it’s inspirational and tells you how it is: don’t let any guy (or anyone else for that matter) define your idea of who you are. Set out to make that definition yourself and do what it takes to do it. Soon the right guy will be knocking on the door – one that appreciates the real you. The guy who sees you for who you actually are. Another point? Turn your flaws into your greatest assets – from your weakness for fashion to your addiction to bad dates. You just have to tune it slightly to turn it from failure to success.

Elle: You’re breaking up with me because I’m too… blonde?

Warner Huntington III: Well, no. That’s not entirely true…

Elle: Then what? My boobs are too big?

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Magic Mike – Because You Deserve a Striptease

So you think you lost someone great. Turns out he wasn’t so great if he never gave you a striptease in the living room where he totally killed it. Magic Mike will. He will seriously save your night.

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The Vow – True Love Lasts Forever

Sometimes you think you have found true love. You are so madly in love with this one guy it seems as if the world will stop spinning when he’s not around. Only, when looking at truly happy couples you suddenly realize that maybe, just maybe he wasn’t all that great. Or he simply just didn’t put in as much effort in the relationship as he should have done. And you deserve the best. You want a relationship that makes the ground shake with love and laughter, not with tears and bitterness. Watching The Vow you will watch one such relationship. It’s a truly inspirational movie about what it means to find love ever after and how much work it takes to keep it when life throws you a screwball, like say, you wife has an accident and forgets who you are.

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How to Lose a Guy in Ten Days – How Not to Date

This is a laugh out loud movie with the benefit of having Matthew McConaughey in it. We all like that six pack, don’t we? It’s also a great movie to remind yourself of all the thing you should’t do when dating…and that there is something beyond the tips and tricks of the dating game as well. There is a true connection we have with some people that survive almost anything. Even everything you do to sabotage the dating experience.

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P.S. I Love You – There’s Life After Becoming a Widow

Breaking up from a relationship you feel you aren’t ready to end is awful. Being widowed when you are blissfully happy with someone is even worse. But there are many journeys we go on in life and when one ends, another begins. However hard it is to leave some parts of our life behind, it’s possible. And as we close one door another one is opened.

This movie is a beautiful account of how one man encouraged his wife to move on after his death by sending her pre-written letters from beyond the grave.

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A Little Bit of Heaven – Because You Are Still Alive

Breaking up is terrible. It can feel like you lost a big part of your life. However, sometimes it helps to remember that you are still alive. That you have this amazing gift called life still in your hands and that you have a chance to make the most of it. Some people are not that fortunate. They didn’t just lose one person they love – they lost their entire life.

This movie tells the story of a woman who discovers she has cancer and as she does, she decides she’s finally going to live. Truly live. Give life and love a go. Turn her last months into a celebration of life, rather than a mourning process.

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The Back-up Plan – Make Your Plans, Then Change Them

Some women feel helpless without men. The opposite is true for J-Lo in this movie as she decides to have children – all by herself. Only, of course, she meets the man of her dreams just after doing so. A great movie if you want to be inspired to take charge of your own life, at the same time as finding courage to let someone new into your life.

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Valentine’s Day – The End of Dating Losers

Sometimes we think we are the loser because we keep dating men who don’t like us. Instead of feeling sorry for ourselves after a break-up it’s a good time to do an inventory if we were dating men that truly appreciated us, or if we were, in fact, dating losers. If we did, then it’s time to start dating men who care. Who really care.

Ashton Kutcher in this movie learns that it’s time to date a woman who cares. And for us ladies it’s rather nice as we get the added benefit of staring at Ashton Kutcher – Mila Kunis, you got yourself a stud!

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Friends With Benefits – Friendship Comes Before Sex

It’s easy to go out into the dating jungle looking for a set of criteria, whilst ignoring the fact that you should be friends with the men you date. Friendship is the foundation for a happy relationship, after all.

In this movie Mila Kunis and Justin Timberlake become great friends. Then they decide that they could just have sex with each other too whilst looking for “the one.” Of course, they are great friends having great sex, so why aren’t they in a relationship? Because relationships are complicated, scary things, right? Yeah, right. Maybe it’s time to do an inventory on what a relationship should truly be like and ditch your old ideas.

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Thelma and Louise – Girl Power

I avoided watching this movie for years. I thought the ending sounded scary. Then one day I sat down and watched it and realized what everyone was raving about. Thelma and Louise might not choose the best of paths to sort their lives out, but there are so many great messages along the way. Do yourself a favor and watch it.

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The Wedding Date – Get the Love Life You Want

An old classic – if you don’t have a date, hire an escort. And sit back to see the complications unfold… Of course, also, always remember the best advice given in movie history by an escort: “Every woman has the love life she wants.” Ouch.

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Amelie – We Can All Find Love

Our lives are all different, as well as kooky, crazy and awkward at times. And somehow most of us find love in the end. The kooky, crazy and awkward love that matches our own kind of crazy. The French movie Amelie once took the world with storm and proved just how kooky love can be. It’s a charming story and just as French as you could wish for it to be.

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Dirty Dancing – Because You Should Never Ever Be in the Corner Again

If you’ve been prone to date people who put you in a corner and forget about you, it’s time to make a change. You need to find your very own oh so hot and sexy Patrick Swazy who promises that nobody will put someone like you in a corner. It may be cheesy, but it’s true. And who can resist drooling over Swazy? A definite feel good factor.

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The Hangover – Laughter Guaranteed

Sometimes when going through a break-up all you need is a laugh. A big roar of a laugh to remind you that there is life after the break-up after all. Although this is a movie about a bachelor party it has little to do with love and more to do with what can, and will, possibly go wrong in Vegas.

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1507760_10152392614860079_8379465670289960282_n copy 2By Maria Montgomery – Maria is a freelance writer, director and social entrepreneur. She’s also the spokesperson for The Little Angels Community Center and an avid blogger. You can find her somewhere between Cape Town, London and L.A., where you will most likely find her in the hills, looking out over the city she loves. @OhMyMontgomery





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