Worst Celebrity Marriage Proposals

Background: In an interview with Vulture, T-Pain was praising FKA Twigs and said, “And she’s engaged now, so that’s about to be a whole other thing… to ol’ Patty [Pattinson]. I don’t know if she wanted anybody to know that.” It was not public knowledge yet. Then, he tried to pass it off as an April Fools joke, which didn’t really work.

Context: After noticing her dog wearing a bowtie, Aidy was immediately thrown off, she told Seth Meyers. “I was like, ‘My dog doesn’t wear a bowtie! 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.’” Watch Aidy tell the full story here.

Context: George told Ellen that he was going to propose to Amal as the song “Why Shouldn’t I” by his aunt Rosemary Clooney played. “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, 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.” LMAO, so casual!!!

Context: “At Christmas time, we go around our family and everyone takes turns opening presents. So I had wrapped the engagement ring in about eight different boxes deep, so she would keep opening boxes to get with it. We finally got to her, and I’m calling my family over. She gets to it, she opens it up, her eyes go wide. I take a knee and I ask her, ‘Will you marry me and take my name?’ The first words out of her mouth were not ‘yes.’ I’m not gonna say what it was,” Matthew told Jay Leno in 2012. “But I did say, ‘Look, I’m down on a knee. I’ll stay here awhile. I will outlast you.’ And I did! She conceded.” The couple now shares two children together, but wow, what an awkward moment. In 2016, Matthew told TODAY that his family also thought Camila was going to reject the proposal.

Context: Peter took Jaime to the Empire State Building, where he had arranged for a plane to fly by with a banner. ‘We were at the top of the Empire State Building, I had it planned. she didn’t know,” he told People. “At 3:55 p.m. she was like I’m cold, I’m going inside. And then all of a sudden I look up and when she went in and the plane was there! I ran inside and I was like ‘You have to come see this!’ And then when I came outside, it was kind of cloudy and I lost the plane in the horizon.” Ugh, it could’ve been so perfect! Buuuut…I guess it was an omen, because the two eventually called off the engagement. 

Context: US Weekly reported that witnesses saw Megan drop the engagement ring mid-proposal. “I saw her jumping up and down,” the witness recalled to the magazine. “Later, I saw a half dozen staff sifting through the sand.”

Context: “So I had all these plans, but the day I got the ring — literally the second I got it — I walked right upstairs to where she was to propose to her,” Seth told Conan. 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 was like ‘Oh man, her boobs are out. That’s not part of the plan. I didn’t picture it like this.’ And I know she didn’t picture it like this.’ No little girl is like ‘It’ll happen in a closet with my titties out.’ But I figured the only appropriate thing was to place the ring on her nipple actually.” L O L.