We all want to win in love. Only Cupid’s on leave, and people are too busy to make efforts in love.

Also, in films, I no longer like to root for couples. It’s like a jinx. You root for them, and they inevitably break up. Not to be dramatic, but sometimes their breakup is equally painful for me, considering how emotionally involved I get.

If you still think that I’m being dramatic, here is a list of some of the most iconic on-screen couples, whose heartbreaking breakups are sure to prove my point.

9 Break-Ups That Broke Our Hearts1. Rick Blaine and Ilsa Lund

Casablanca (1942)

Casablanca follows Rick (Humphrey Bogart), and Ilsa (Ingrid Bergman) , who never get their happy ending amid politics, societal expectations, and moral obligations.

Their love story is a cruel game of fate. Why’d they even have to meet and fall in love if their love story was bound to meet such an abrupt end? It was especially unfair to Ilsa to have to choose between the man she married and the man she loved.

For Rick, Ilsa’s abandonment without closure took its toll. They had come to believe that it was all over, but fate brought them face to face once again, only to conclude their romance forever.

2. Jimmy a.k.a. Saul Goodman and Kim Wexler

Better Call Saul

This is hands-down my favorite couple in recent years. Jimmy (Bob Odenkirk) and Kim (Rhea Seehorn) are lawyers, perfect for each other, basically soulmates. If only Jimmy had a bit more luck and compassion on his side, he and Kim would’ve never had to give up on their happy ending.

Their breakup is gradual, and it is painful to witness these two slowly outgrowing each other until one day it’s really over. The most heartbreaking part? They don’t break up because they’ve fallen out of love, but to keep each other safe.

3. Carol and Therese

Carol (2015)

In 1950s New York City, two women falling in love was unthinkable, let alone having a public relationship. However, despite all odds, the love blooms. Honestly, a happy ending for their love story would’ve been a pleasant surprise, considering their circumstances—a divorced single mother in her 40s and a young aspiring photographer.

However, hope is a silly thing, and there was some part in me that definitely wanted them to end up together. When Carol (Cate Blanchett) leaves suddenly, leaving a note for Therese (Rooney Mara) explaining her limitations as a mother and a woman in this brutal society, you mourn the end of their love alongside Theresa. Sometimes, there’s nothing else to do other than accept that love falls short.

4. Su and Chow

In the Mood for Love (2000)

Two people forming a connection over their misery and eventually falling in love—sometimes I feel Wong Kar Wai’s In the Mood for Love deserves an alternate ending in which Su (Maggie Cheung) makes it in time to leave for Singapore with Chow (Tony Leung). They deserved to be happy together after losing so much in love and marriage.

Both of their spouses were cheating on them; at least together, they’d be happy too. Only good things seldom happen to good people.

5. Mia and Sebastian

La La Land (2016)

Mia (Emma Stone) and Sebastian (Ryan Gosling) meet at the wrong time in their lives. Amid the hustle of achieving their professional dreams, it’s only natural to fall short in maintaining a relationship. So there comes a point in their relationship where they have to decide between their dreams and their love.

The two respectfully choose the former and part ways amicably. When they break up, they promise to love each other forever, even if they never end up together. In the end, the final nod proves how both of them kept their word, unconditionally— a love so pure that it chooses you even when you don’t choose it.

6. Daniel And Miranda

Mrs. Doubtfire (1993)

Mrs. Doubtfire may be a rom-com, a fun ride following a dad desperately trying to fulfill his fatherly duties at any cost, but it also features one of the most heartbreaking breakups.

After 14 years of marriage and three kids, when your partner tells you that the two of you are too different to have a life together anymore, where do you go? What do you do? You probably do what Daniel (Robin Williams) did—beg and plead with the person you love to rethink their decision. But begging in love rarely gets you anywhere.

7. Jane and Tom

Becoming Jane (2007)

Becoming Jane is based on Jane Austen’s life. So, to think that this break-up happened in real life breaks me a little from the inside.

Jane (Anne Hathaway) and Tom (James McAvoy) are engaged, all set to begin a new life together, when Jane learns that Tom is the only breadwinner in his family. Eloping with her meant that they would have their happy ending, but only at the expense of his family. Jane doesn’t allow that and breaks up with Tom.

While their breakup is beyond painful to watch, their meeting years later, after they have established separate lives without each other, reminds us that life goes on, with or without them!

8. Francesca and Robert

The Bridges of Madison County (1995)

Francesca (Meryl Streep) is a simple housewife who finds herself in her greatest dilemma when she falls in love with Robert (Clint Eastwood), a traveling photographer, and he asks her to leave her old life behind to start a new one with him.

What would you have done if you were Francesca? Would you have thrown away your old life to start a new one with your soulmate? I believe there is no right answer to this question, so deciding this is something I wouldn’t wish even on an enemy.

Francesca breaking down as she ends her relationship with Robert is probably one of the most painful breakups you’ll ever see. And to know that she never stopped loving him? Ugh! Why do people who’re perfect for each other always end up meeting at the wrong time in life?

9. Emma and Adéle

Blue Is the Warmest Color

Most of the time, life gets in the way of our relationships.

Blue Is the Warmest Color follows Emma (Léa Seydoux), a shy girl on the brink of adulthood who falls in love with Adéle (Adéle Exarchopoulos), a mysterious blue-haired woman, a relationship that changes her life forever.

At this point in the story, with Emma engrossed in her career, Adéle feels herself growing even more alone and out of place. Then one day, she ends up cheating on Emma with a man. When Emma finds out, she explodes. She literally throws out Adéle, breaking up with her.

Between Emma’s rage and Adéle’s begging and crying for forgiveness, you stand there witnessing two people deeply in love fall apart.

Did we miss any? Let us know which one of these breakups was the most painful for you.