3 of the Worst Celebrity Proposals and How to Avoid Them

George Clooney's proposal to Amal was a little tougher than expected. . .

Proposing to the partner of your dreams can be a lot of pressure. Of course you want this moment to be just right, but setbacks can happen—even to the stars. Check out these celebrity proposals gone wrong and learn from their mistakes.

Matthew McConaughey and Camila Alves
Some people have such a tight-knit family that they may want everyone—literally everyone—they love to be witness to the big event. Matthew McConaughey opted to pop the question with a Christmas Day proposal to Brazilian-born model and designer, Camila Alves, in front of the entire McConaughey clan while opening gifts under the tree on Christmas morning. In the McConaughey tradition, each family member takes turns opening gifts. When it was finally Camila Alves’s turn to open her present from Magic Mike star Matthew McConaughey, a three stone diamond engagement ring wrapped in “about” eight boxes, it sounds like waiting for her answer felt like an eternity as the Texas-born star recounts the story to Jay Leno. The smooth talking celebrity dropped to one knee, asking Camila Alves to be his wife and take his name, and heard crickets (or expletives, depending on who you ask). What would you do? Matthew McConaughey held out on one knee, declaring, “I will outlast you!” And he did. The comely pair has been wed for more than five years and has three beautiful children together.

Takeaway: Not everyone is up for an on-the-spot proposal in front of oodles of extended family members. Try to get a feel for how your honey will react. How the family will react. If you’ve gotten to the point where you’re ready to buy an engagement ring and pop the question, chances are your beloved will answer with a resounding YES! But, if you’re not sure you have the fortitude of Matthew McConaughey in the face of an uncertain answer, try dropping a few hints about your special holiday/Christmas present a few days or hours in advance, to give your intended a heads-up that something big might be in a little box!

Ben Stiller and Christine Taylor
Buying a diamond engagement ring is one of the biggest and most stressful tasks anyone can take on in life. Alongside buying a home, it’s one of the most emotional purchases anyone will ever make. Funny man Ben Stiller wasn’t laughing when, having flown from New York to Los Angeles to propose to then-girlfriend Christine Taylor, he realized that he didn’t have the ring. Ben Stiller had filled Ms. Taylor’s house with candles and roses, only to realize at the crucial moment, on bended-knee, that he had forgotten the engagement ring. In true improve form, he took the setback in stride, asking his bride-to-be to, “Hang on a second!” He sprinted to his luggage, retrieved the ring and resumed the super-romantic proposal. She said, “Yes, of course!”

Takeaway: There’s always duct tape. Do everything you can to remind yourself to hang on to that engagement ring, and hang on tight. Oh, and insure that ring with your homeowner’s or renter’s insurance policy, too—especially if you plan to travel with it—

Theres nothing worse than losing the engagement ring during or soon after the proposal, when you haven’t had a chance to think about logistics. However, as Ben Stiller and Christine Taylor prove, love will find a way.

George Clooney and Amal (Alamuddin) Clooney
It took 25 minutes for Amal Alamuddin, just back from London, and ready to order takeout, to realize that George Clooney, activist actor, had made her a special dinner and lit candles for a very good reason. The seemingly sworn bachelor fell immediately in love with Ms. Alamuddin, a high-profile Lebanese-British international human rights lawyer, when he met her, and he just knew right away they would be together. Mr. Clooney was ready to pop the question, but Ms. Alamuddin took her time to answer. The former TV doctor had hidden the ring away, and when he prompted her to find it, in all the excitement, she didn’t register at first that the ring was hers, not something someone else had left behind. Awkward. The charming star dropped to one knee and presented her with a stunning engagement ring. Once she realized that their 6-month courtship had come to happy end—an engagement!—her answer was a an emphatic YES.

Takeaway: When you know, you know. But it may take your future partner a few minutes to get up to speed with the plans you’ve taken such care to make. Give her a few minutes to process the momentous occasion, and don’t get too nervous!

No matter where you are in the proposal process, we’re here to help. We love working with all budgets, and consider it a challenge to find the perfect ring for each of our couples—it’s our passion!

Call 720-323-9909 or click below to schedule your private appointment with Denver’s top diamond expert.


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