10 Most Painful Breakups in TV Shows

'Better Call Saul' – Jimmy McGill & Kim Wexler

The breakup of Jimmy and Kim is arguably the most heart-wrenching event in Better Call Saul. They share a connection based on their love for each other, their trust, and their ability to be morally gray. Kim’s reason for leaving is not that she no longer loves Jimmy, but rather she understands that being around him makes her worse than who she really is. The calm and quiet manner in which she exits is what makes this scene so heart-wrenching.

'This Is Us' – Kevin & Sophie

The end of the relationship between Kevin and Sophie is a significant emotional event since it has been going on for quite some time. Their story includes years of loving each other, making mistakes, and trying to patch things up. The dissolution of this relationship is not merely the end of one that had been a short fling but something far more substantial.

'Sex Education' – Otis & Maeve

Otis and Maeve's breakup is characterized by lack of timing, repressed feelings, and bad luck. It seems that every time they are on the verge of starting their relationship, something comes in between; either geographical distances, relations with other people, or the failure to confess to each other about their feelings. What makes the whole breakup more devastating is the accumulation of built-up emotions throughout several seasons.

'Euphoria' – Rue & Jules

The separation of Rue and Jules is extremely devastating since the break-up stems from problems related to addiction and dependency. Problems that Rue experiences with her drug addiction contribute to creating such an unhealthy environment that it becomes impossible for Jules to stay in it any longer. It does not come from any loss of affection, but rather a need for a separation that will be beneficial for both partners.

'Normal People' – Marianne & Connell

The breakup of Marianne and Connell’s relationship is perhaps one of the most realistic depictions of emotional misunderstanding in contemporary television. It does not come about through disagreement, but through the failure to express how they truly feel in the appropriate moment. The gap that exists between them proves to be much more detrimental than any form of conflict. As a result, their split proves highly frustrating, knowing full well that they both love one another but cannot connect emotionally.

'How I Met Your Mother' – Ted & Robin

The breakup between Ted and Robin hurts immensely since it stems from incompatibility, and not from their love. While Ted envisions himself with a family someday, Robin knows that she wants none of that. Although it may seem to be a mature decision on their part to break up, they hurt each other tremendously, and for the reason that they are both completely innocent. It hurts even more because it seems like love will not be enough for both of them.

'Friends' – Phoebe & David

Phoebe and David’s story can easily be ranked among the saddest in Friends without a need for any overt displays of anguish or hurt feelings. Rather than a classic separation, their parting is all about timing. David leaves Phoebe time and time again in order to pursue his dream of becoming a scientist, and every get-together ends in the promise of something wonderful happening, which unfortunately fails to come true.

'Friends' – Ross & Rachel

The split between Ross and Rachel has been one of the most controversial events in television history. It is a story that begins well, but is soon torn apart by a combination of jealously, insecurities, and an extremely poor decision made in a moment of utter misunderstanding. The “we were on a break” issue only makes their situation even more complicated, leaving the two heartbroken in their own way. Their separation was extremely painful for everyone involved since it seems so avoidable. Fortunately, they got back with each other in the end.

'Grey's Anatomy' - Meredith and Derek

Meredith and Derek’s relationship in Grey's Anatomy stood out for its repeated heartbreak and unresolved tension. Addison’s arrival in Season 1 exposed Derek’s marriage, breaking Meredith’s trust early on. Season 2 brought her emotional “pick me, choose me, love me” plea, yet he chose Addison. Later seasons showed ongoing struggles, including trust issues and mismatched expectations. Even when they reunited, stability never lasted. Their story ended in Season 11 with Derek’s sudden death.

'Sex and the City' - Carrie and Mr. Big

Carrie and Big’s relationship in Sex and the City wasn’t just about one breakup—it kept happening again and again. Every time Big walked away, Carrie got hurt a little more, even though she still loved him. She kept hoping he would finally choose her, but he never fully did. That’s what made it so painful to watch. Their story showed how hard it is to let go of someone who gives you just enough to stay, but never enough to feel secure.