Gilmore Girls: The most heartbreaking Rory moments that still hurt to watch

Which show do you want to watch when it's raining outside and you're curled up in your bed, wrapped in your cozy blanket? If you said Gilmore Girls, then you are goated. It is a show that makes everyone wish they had the same love for coffee, and every daughter wishes that she had the same bond with her mom as Rory and Lorelai.

Despite all the fun banter, fast-talking humor, and heartwarming moments, Gilmore Girls has some moments that break the heart. Those moments hit even harder when it comes to Rory Gilmore. She is the daughter of Lorelai Gilmore, whom fans watched transform from a shy teenager into an ambitious young woman.

She is a smart and kind girl, and still life didn't spare her from heartbreak. She encountered broken relations, career setbacks, and dark moments of self-doubt, and watching her deal with each one felt real.

The most heartbreaking Rory moments on Gilmore Girls

Revisiting these old wounds on Gilmore Girls may be painful for some fans, not because it's hard to see our golden girl, Rory, in pain, but because these moments make fans realize how human she is. These scenes tend to evoke the same feelings in fans that they did the first time they watched them.

1) Rory misses the Harvard interview

If there was something that Rory strived hard to achieve, it was to get into Harvard. That dream was close to being achieved if life had followed Rory's plan, but Richard had other plans. Her small mistake crushes her dreams, and the emotional weight of that moment is hard to carry.

Rory spends the whole night preparing for the interview, but forgets to set an alarm for the next day. She ends up oversleeping, causing her to dash frantically to the interview and eventually realize that it's too late. All her hard work was wasted in that one moment.

2) Rory and Dean's breakup

Everyone's first love is always special, and the first breakup always hits the hardest. Dean was her first love, and their love had a pure, youthful glow. Although they broke up three different times over the course of the series, the first one was especially difficult.

Dean expressed his love for Rory, but she found it hard to say it back to him. Feeling dejected and disappointed that she didn't feel the same way, he broke up. Seeing the look on her face, full of confusion and pain, feels like an emotional gut punch.

3) Rory's rift with Lorelai

Rory and Lorelai's bond was the heart and soul of Gilmore Girls. It was the foundation that carried the show for seven seasons. So, watching their relationship fall apart when Rory decided to leave Yale was unbearable. Watching a wallowing Lorelai alone and Rory being stubborn made their reunion even more special.

4) Rory's affair with Dean

First loves are difficult to forget, and Rory proved that when she decided to have an affair with a married Dean in Gilmore Girls Season 4. It was difficult to watch because it was completely out of character for Rory.

She had always been a thoughtful and principled girl who always followed a moral compass. Watching her slip from her righteous path and ignoring her values wasn't on anyone's wishlist and was particularly hard to watch.

5) Rory's Yale break-in and arrest

Throughout Gilmore Girls, Rory has always been a morally driven girl who was always responsible and guided. But even the most righteous sometimes have a lapse of judgment. That moment came for Rory when she decided to join Logan in "borrowing" a yacht, which resulted in her arrest.

Watching her being escorted out in handcuffs, and the fear and shame being visible on her face, was jarring. It was a moment that made every Gilmore Girls fan feel like a parent whose child's future hangs in the balance.

6) Rory drops out of Yale

After a harsh critique from Logan's father, Mitchum Huntzburger, a leading figure in journalism, Rory takes the most difficult decision of her life: a break from Yale. His words that she lacked the necessary "it" factor needed to become a successful journalist made her question her dream and shook her confidence.

The rejection prompted her to recalibrate her compass and take a break from a semester to gather herself. Watching her pack up her belongings with dimmed eyes felt personal to anyone who questioned their path.

7) Logan's proposal and Rory's goodbye

Gilmore Girls had some sweet couples, and Logan and Rory were one of them; they cared deeply for each other and loved unconditionally. Their relationship was far from being perfect, but there was mutual respect and admiration that remained throughout. Which is why, when Rory refused Logan's proposal, it did turn ugly; it was gut-wrenching but respectful.

Rory turned Logan down because she felt that marrying him would limit her independence and the opportunities that were to open for her after her graduation. Both were mature about their breakup and understood that sometimes love doesn't stand a chance when life pulls you in different directions.

8) Rory's career setbacks

In the final season of Gilmore Girls, Rory suffers many career setbacks, and each setback dips her confidence and makes her doubt herself. Incidents like getting fired from her ghostwriting gig, falling asleep during her GQ assignment, and an unfortunate arrogance episode during an interview that jeopardized her prospects of getting the job.

For a girl who was always an ace student, dealing with these setbacks was a painful task, but it eventually proved to be a life lesson as she stepped into adulthood.

9) Rory says goodbye to Jess

Gilmore Girls had some epic romances and tragedies that could give tough competition to William Shakespeare. Especially Rory, who was the victim of some excruciating heartbreaks. One of them was her breakup with Jess. Their relationship timeline was full of complications and unspoken feelings, and the confusion and sadness compounded when Jess suddenly disappeared on her.

Jess was unstable and immature, and he left Stars Hollow unexpectedly to meet his father without telling Rory. She realized that she loved him, but had to move on because a stable relationship with Jess wasn't possible at that time.

10) Rory says goodbye to Richard

Saying goodbye to a loved one is always heartbreaking, especially when it's a grandparent. Rory faced a devastating moment when her grandfather, Richard Gilmore, passed away. Her grief was heavy, but she tried her best to support Emily and Lorelai.

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These tender moments from Gilmore Girls don't linger in the hearts because of the sheer sadness, but because they match the unpredictability and chaos of real life. People misstep march forward win some and lose a lot in the process of finding themselves. Rory reflects that journey perfectly and is the perfect example that growth comes with pain.