Sometimes experience an intimacy with your child ’s nanny is enough to call it throw in the towel the first clip …

Celebritybreakupscan be sad, messy, and straight-up chaotic. But celebrity engagement breakups? That’s next-level tragic.

These 14 couples were thissss close to tying the knot, but never made it to the altar. Here are some of the most iconic, surprising, and totally unexpected celeb pairs who almost said “I do”…then didn’t:

1.Lady GagaandTaylor Kinney

2.Julia RobertsandKiefer Sutherland

3.Ryan Reynolds and Alanis Morissette

4.Ariana Grande and Pete Davidson

5.Katie Holmes and Chris Klein

6.Demi Lovato and Max Ehrich

7.Gwyneth Paltrow and Brad Pitt

8.Channing Tatum and Zoë Kravitz

9.Ben Affleck and Jennifer Lopez

10.Sienna Miller and Jude Law

11.Rachel Bilson and Hayden Christensen

12.Mark Ronson and Rashida Jones

13.Sandra Bullock and Tate Donovan

14.Zayn Malik and Perrie Edwards

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Person lying on a couch, visibly emotional, face scrunched in distress and tears, portraying a moment of intense emotion or reaction

Two people posing at an event. The person on the left is wearing an elegant white dress with a high neckline and peplum detail; the other is in a tuxedo

Two celebrities on red carpet; one in a long, elegant dress, the other in a classic tuxedo. Both are smiling and posing for photos

Celebrities on a red carpet. The man wears a casual white shirt and dark pants. The woman is in a metallic, off-shoulder dress and thigh-high boots

Two individuals pose on a red carpet. The woman wears a sleeveless, knee-length dress. The man is in a button-up shirt and trousers

Two celebrities smile on the red carpet, holding hands. She wears a shimmering slip dress; he's in a classic black suit with sunglasses

Two people on a red carpet; one in a black suit and tie, and the other in a sleeveless red dress with a belt, smiling at each other

A couple on a red carpet: one in a suit and tie, the other in a strapless gown with a voluminous skirt and long gloves, smiling at each other

A man and woman on a red carpet. The woman is wearing an elegant deep V-neck gown with intricate detailing, and the man is in a classic suit and tie

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Two people pose on a red carpet. A woman wears a stylish crop top and skirt set, and a man wears a suit with a patterned tie