The Most Hilarious (& Relatable) Celebrity Engagement Stories

Everyone’s favorite celebrity couple might seem picture-perfect, but their proposal was anything but. “I wanted to be the cool girl, so I never pushed the marriage topic very much, but you know how it is,” she recalled on FABLife. “I remember we got into a very big fight in the car, because we had opened our presents beforehand, and he had only gotten me a cookbook and a Crock-Pot … We get to the Maldives, and he had planned this beautiful Christmas … the waiter comes out with a silver dome for dessert, he opens up the dome and a ton of arugula falls out, and I just fish in it. And John was like, ‘This is not going well.'” Mishaps aside, Teigen admitted that her “heart stopped.”

The Saturday Night Live star admitted that she thought the proposal was a joke when it first happened because she was so caught off guard when she came home and found their dog wearing a bow tie. “I was like, ‘My dog doesn’t wear a bow tie! Where is he going tonight?’ Basically, the second I shut the door, a man — who I discovered was Conner — frantically came around the corner and was just like, ‘Will you marry me?!’ No box. No ‘I love you,’ ” she told Seth Meyers. “Just a man in full terror standing very far from a dog in a bow tie, just holding a loose ring going, ‘Will you marry me?’ I was like, ‘What?’ “

The funny man had grand, romantic plans when he decided to pop the question, but once he actually picked up the ring, things got a bit … NSFW. “I was just so nervous when I got it. I couldn’t have a conversation with my girlfriend, all I could think [about] was this ring,” Rogen recounted on Conan. “I had all these plans, but, like, the day I got the ring, literally the second I got it, I walked right upstairs to where she was to propose to her, but she was in our closet changing, and she was literally only in her underwear and her boobs were out. And I had already kind of started … I figured the only appropriate thing was to place the ring on her nipple.”

Plenty of women dream of being proposed to by Clooney, but when he popped the question to his now-wife, she was, well, underwhelmed. “I’ve got it all set up, timed out and the song is coming, and she gets up to go wash the dishes, which she’s never done,” Clooney recounted to Ellen DeGeneres on her show. “And I’m like, ‘What are you doing?’ and she comes back in. And finally I said, ‘Ya know, I blew out the candle,’ and I said, ‘I think the lighter’s in the box behind you.’ And she reaches around and she pulls out the box, and I’ve got just the ring sitting in there, and she pulls it out and she looks at it, and she’s like, ‘It’s a ring’ — like as if somebody had left it there some other time.” It took 25 minutes for Amal to answer him, but she did — eventually — say yes.

Learn from Stiller’s mistakes, and make sure to remember the ring if you ask someone to marry you. “I flew from New York to L.A. to surprise her. I put candles and rose petals leading through her house to the back deck, where I was waiting; it was really cheesy and romantic,” he told Parade about sneaking into Taylor’s home. “She sensed when she saw the petals that it was a friendly intruder. I got down on one knee and then realized I had totally forgotten the ring! So I was like, ‘Hang on a second.’ I had to run into the other room and get it out of my backpack.”