When I proposed to my wife, I thought about all the over-the-top gestures, then pictured it going haywire and ending up in a viral Reddit post about how dumb I am. So I opted for a nice, calm proposal in our first apartment together. It worked out perfect.
I’ve witnessed some awkward proposals, though. I was doing a show once, and about 10 minutes before it started, a guy from the audience asked if he could propose to his girlfriend during the show. I should’ve said no, but I wanted to see what would happen if I said yes.
Well, that moment came, and man, the look of surprise and confusion on her face when he got down on one knee was exactly what you’d expect from someone realizing they’re dating a guy who’d propose at a stand-up comedy show. One headlined by me, which made it even better. Better for me, worse for her. I hope they’re doing well.
1. “Storm Chaser Proposed With Kansas Tornado In The Background”

2. “She Said No”

3. “A Perfect Time To Propose. Bridesmaids Friend’s Wedding”

4. “No Better Way To Propose Than On The Front Of A Portaloo”

5. “I Do Love Olive Garden Breadsticks. But…. Dang”

6. “Just A Suggestion On How To Propose”

7. “So My Friend Proposed Like This To His Girlfriend”

8. “Etching Your Proposal Into Ancient Rocks At A Popular Look Out In The Blue Mountains”

9. “Taco Bell: For The Big Moments In Life”

10. KFC Marriage Proposal

11. “Missus Wants Me To Pull Out All The Stops When I Eventually Propose. I’ve Kept This Bad Boy For Two Years”

12. “A Marriage Proposal”

13. “When You Get The Prime Spot So The Guy At The Back Has To Propose By A Bench”

14. “Proposes With A Ring In A Can Of Dip”

15. “Not Even Asking”

16. “It’s Giving Underage Proposal”

17. “Trashy Proposal”

18. “This Guy”

19. “A Woman I Know Runs Marathons And Just Got Proposed To Via Sneakers”

20. “What Better Place To Propose Than At An Amway Conference?”

21. “Marriage Proposals Like This”

22. “Well Fellas This Guy Just ‘Rolled Back’ The Bar On Marriage Proposals”

23. “Happy Birthday Or Happy Proposal?”

24. “He Proposed To Her At ‘It Works’ Event… Using Engagement Photos To Promote Your Product. Such A Class”

25. “My Friend Woke Up To This During The Week! A Clothing-Created Marriage Proposal”

26. “Will You Marry Me Precious”

27. Marriage proposal on Coca Cola bottles

28. Chewing Tobacco Wedding Proposal

29. “So The Terrible Marriage Proposal Thread Reminded Me That This Happened At A Crowded Beach A Couple Of Years Ago”

30. “The Classiest Proposal I’ve Ever Seen! Also In Walmart”

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Nate writes for Pleated-Jeans and enjoys finding the internet’s funniest corners so you don’t have to.

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