Wedding & Event Planning
101 Ways to Propose Marriage
Scott E. Jones has been working as a DJ, entertainment booker, event planner and office manager with Jerry Bruno Productions (now Cleveland Music Group) for nearly a decade. During his countless meetings with newly engaged couples, he has always asked one question: “How did you propose?”
Scott kept a list of all the answers he has received over the years and compiled them. Here they are for your reading enjoyment or idea stimulation. Feel free to comment and share your proposal story!
Note: we’ve left in many of the locations as told to us, but feel free to replace with your own!
1. Clean the house, make dinner, then hide signs for her to follow that lead to your heart. You’ll be there with the ring in hand. Add a poem in the actual proposal that she’ll never forget.
2. While scuba diving, under water, hide the ring in a treasure chest off the coast of Key West.
3. Hide the ring in her breath mint tin, then ask her for a mint.
4. In a Gondola in Venice (or the fake one in Vegas) as the gondolier serenades you. Remember to kiss under each bridge!
5. Have the jumbo-tron ask for you during the 7th inning stretch at a ball game’s season opener.
6. At a family gathering such as a birthday party, 4th of July cook out or Labor Day picnic. TIP: It may not be a good idea to propose at a Wedding, rehearsal dinner or Baby Shower. Those are events for someone else’s big day.
7. On bended knee. This is very traditional and can be done at any time, any place. You can mix this into any of the listed 101 ways to propose.
8. While skydiving, tandem or solo. For added flair, make the landing spot spell out “Will You Marry Me?”
9. If you are serving our great country in the Military, contact a talk show to see if you can propose live via satellite hook up to your post. One of our grooms did this on Late Night with David Letterman.
10. While strolling through Central Park on a beautiful fall evening, sipping on a Starbucks double latte mochaccino.
11. Rent out a movie theater. Instead of playing a movie, play a video created by you: a slide show of your favorite photos or a video you’ve made for the occasion. Read the detailed story about our tricky and romantic groom who pulled this off.
12. In a hot air balloon. Any location will do, but our groom proposed while flying high over Cab San Lucas, Mexico on their 2nd anniversary.
13. After you watch the Survivor Season Finale’ and your favorite contestant just won.
14. After grace, on Thanksgiving Day at the bride-to-be’s parents house in front of all the family. (Don’t forget to ask Dads’ permission first if they are a traditional family.)
15. At the stroke of midnight on New Years Eve. This would be a good time to get on bended knee.
16. Don’t tempt fate. Almost lose the ring? Propose then and there! One groom saved the ring from a small kitchen fire and proposed on the spot.
17. Wrap the ring in increasingly smaller boxes to be opened on Christmas Day.
18. Wait ten years and just pop the question while making dinner in a “matter-of-fact” manner. (Expect a few swear words from your future bride).
19. In front of Claude Monet’s “Water Lilies” at an art museum. (You might say something like, “let’s make this moment and this art we’re enjoying even more beautiful with this engagement ring.”)
20. On a boat, cruising Lake Erie, under the stars. (You might casually broach the subject by saying, “Hey, I talked to your dad today. He said I could marry you.”)
21. On your first date anniversary during an Adam Sandler movie-thon.
22. In front of the reflection pond at the Cleveland Museum of Art on Valentines Day.
24. Too nervous to bring it up yourself? Inform the gossip queen of the family and have her spread the word for you until the bride-to-be hears it through the grapevine. She’ll bring it up for you, and fast! Be ready with the ring at all times.
25. At a friend’s birthday party, hide the engagement ring in the bride-to-be’s purse hooked on to her cell phone. Get her attention by calling her phone multiple times until she picks it up.
26. Without actually proposing, if you wait long enough, she will weasel it out of you.
27. In Central Park, New York, on a bridge overlooking the Ice Rink after your carriage ride through the city.
28. Make a rose petal trail from the door to you. Wait for her with ring in hand and a bottle of her favorite red wine when she arrives home from a long day at work.
29. In Paris, France, on top of the Eiffel Tower in the month of May.
30. Have it written in smoke by an aerobic pilot over the park during your surprise picnic.
31. At the very moment you realize the one you love is the only one that matters.
32. Attach the ring to the new puppy’s collar and have the puppy fetch the one you love. (Don’t forget to attach a note to the puppy too, dogs can’t talk)
33. While making snow angels in your parent’s front lawn at 2:00 AM.
34. While crossing hemispheres on board a jet, en route to your Australian vacation for two.
35. In a rose garden with your other “love,” (a new puppy) after it gives your bride-to-be a wet doggie kiss.
36. Take her to see her favorite band. Find someone in charge and ask if the band will ask for you or bring you on stage.
37. At the Bellagio Hotel in Las Vegas, atop the Garden Room balcony.
38. After a car accident or other scary moment. Relieve the tension quickly by turning a frightening moment into a grand one.
39. While standing on the corner in Winslow, Arizona without a fine site to see. (Hint: this is from an Eagles song. Does she have a favorite song that mentions a location?)
40. On a beach in the pouring rain. (I would suggest Seal Beach located in southern California, it’s beautiful.)
41. In a park, on a marry-go-round, after your best friend’s wedding ceremony (before or after their reception, but if it’s before, make sure you let the couple enjoy their big day as you wish to enjoy yours).
42. At the jewelry store, right after you and your loved one go to look at engagement rings “just for fun.”
43. After her father or mother successfully makes it through a surgery.
44. Show up at her workplace and surprise her (again, bended knee here would be a great touch).
45. Plan a wonderful evening/weekend at her favorite bed & breakfast. Propose while you read the morning paper over a cup of coffee and an orange juice.
46. (If you keep a journal and wrote in it that you were thinking of proposing.) On your anniversary, return to where you were when you first thought of proposing. Bring your journal and read the entry to her.
47. After a long fight over something silly, smooth over the tense feeling with a ring that was on it’s way anyway!
48. At Whips Ledges in Hinckley, Ohio at sunset.
49. Drive home from college and surprise her on her front doorstep with roses (bonus if it’s raining).
50. After being shot down by her after your first year of dating, wait another seven years for her to propose to you.
51. At 10,000 feet on Lake Tahoe California’s Heavenly Ski Resort’s highest peak, after a nice packed lunch.
52. Type the proposal into the startup screen of the new Palm you got her for her birthday!
53. At home right after brunch before you start the dishes.
54. Have a police officer friend she doesn’t know? Ask him or her to pull you over and search the car. Let the cop find the ring in the car so that you can propose to her on the side of the freeway.
55. With symbols of your life and family in hand, ask her to be a part of what you love.
56. Have a Chinese Restaurant make a fortune cookie with the ring in it and the proposal on the fortune. Or insert into a fortune cookie yourself.
57. Helping her move? While handing her some moving boxes, give her the extra little one with the ring in it.
58. Pay the chair lift guy at a ski resort to stop you half way up the mountain for your surprise in mid-air. (Bonus if she’s afraid of heights!)
59. Pretend to fix the sink drain clog by pulling out the problem (the ring).
60. After fixing her car’s flat tire (again, bonus if it’s raining).
61. At the Casino Windsor Hotel with a dozen roses for every year you’ve been together. Place rose petals on the floor of the room, shape a flower with the petals on the bed.
62. After a crazy night in the E.R. (Our bride’s E.R. visit was due to a toothpick in the foot at Mapleside Farms, her favorite restaurant.)
63. At the peak of the Grand Canyon where the first hotel once stood.
65. On a beach off the “Road to Hanna” in Maui at sun set.
66. While pretending to read a book or magazine, nonchalantly ask her to type “zult u me huwen” into a translation web site for you. (It’s Dutch for Will You Marry Me? You might choose the language of her ancestors.)
67. Two days after you told her you weren’t going to be ready for another year or so to be married. (Be sure she’ll wait a year…or two days for that matter.)
68. After a special dinner at your home on Valentine’s Day. Bonus if you’re in your sweatpants.
69. At Laguna Beach in California with a bottle of wine at sunset.
70. At a funeral reception for a family member of your bride-to-be. (Yes, this happened.)
71. By hiding the ring at the top of a toothpaste container; surprise her the next time she brushes her teeth.
72. Rent a billboard sign to be seen by passersby (and her) on a local highway.
73. At a local bar you frequent when the moment feels just right.
74. Present her with a PowerPoint presentation of why you would be good together.
75. In Las Vegas at a drive-through chapel.
76. Take her out to dinner where a magician does table magic. Pretend to go to the bathroom and give him the ring so he can make it appear in front of her eyes at your table!
77. Under water while snorkeling at Xel-Ha in Mexico.
78. While flying a kite. Attach it to the string and ask her to come help you.
79. In North Carolina on a pier into the Atlantic, while she is ranting, pull out the ring and say: “Do I have to ask?”
80. Create a scrap book of your lives together so far and give it to her for her birthday with “Will You Marry Me” on the last page. Bonus: Hide a video recorder and tape her while she looks through the book.
81. Does she give you her ring finger as a joking middle finger every time you argue about getting married? The next time she does it, just pop the ring on her finger.
82. On a beach while picking up shells, say, “Wow, look at this one!?” and hold the ring out for her.
83. At the Biltmore in Arizona, have the waiter bring the ring, flowers and wine out on a silver tray.
84. In a hot tub at an Amish log cabin, on a cold winter night by a fireplace.
85. On your anniversary, give her a T- Shirt that says “Happy Anniversary” on the front, and “Will You Marry Me?” on the back.
86. In a wedding gazebo in St. Thomas.
87. Put the ring around the hook of an ornament and hand it to her while decorating the tree.
88. While cuddling on the couch, watching cartoons on a Sunday morning.
89. At 7am after making breakfast. Present the ring to her with a glass of mimosa and breakfast in bed.
90. Surprise her while she is on a business trip. Walk up to her with a ring in hand and say: “Hey I’m in town too, will you marry me?”
91. On Christmas morning, after eating yummy cinnamon rolls, under the mistletoe.
92. While trimming the tree, hand her three hand-crafted ornaments in order: “Will,” “You,” “Marry Me?”
93. Having her un-wrap a 5 foot tall engagement ring you made out of scratch for her.
94. Dress up like Santa Clause for her office Christmas Party and surprise her when she sits on your knee.
95. Burn it into the lawn with gasoline. (Not recommended, but it did happen.)
96. Arrange a day of luxury for her and end it at a suite in The Ritz-Carlton. Convert the room ahead of time into a “French Restaurant.”
97. The next time you see a rainbow together, stop right where you are and propose. If you don’t have the ring on you, she’ll understand.
98. Hire a celebrity impersonator who portrays someone she admires and ask them to perform just for her and give her the ring.
99. Ask the cast of your local High School’s play to help organize a “dry rehearsal.” Trick her into attending “Opening Night,” in which the school kids come to center stage and ask her in unison if she’ll marry you.
100. Propose in your Facebook or Twtitter status.
101. Change your Facebook relationship status to “Single.” When she yells at you (probably within an hour of the change), tell her you don’t want to be single any longer, and present the ring. Or, set it to “Engaged” or “It’s Complicated” and wait for her to bring it up (again, it won’t be long).