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Proposals Gone Wrong

Updated: Jan 12, 2023

"Why should I hire a proposal planner?" Proposals of San Diego's Event Coordinator Jasmine Jimmerson explains.

Have you ever asked yourself, “What’s the WORST that could happen?” or “What could possibly go wrong?” Imagine arriving at a beautiful restaurant only to have another couple surprise everyone in the room with their proposal, moments before yours!? Proposals of San Diego have been a part of helping many gorgeous couples avoid disasters like this. Using the service of a proposal planner could be a wise choice for you, according to Jasmine Jimmerson, Event Coordinator with Proposals of San Diego.

Usually you use that phrase when you have the complete confidence to do something. It is almost always followed by a nagging shadow of "what if my proposal fails?" Many people discover those exact moments after the fact that they were cursed by the phrase.

It goes a little something like this… the energy is sparking powerfully with a special someone. You have high hopes born of promising experiences. Already convinced that the person you have decided on is also on the same page as you. You are ready to begin a new chapter in the story of your lives - merging the story lines into one. This is the part you plan out... you decide it is better to be spontaneous… make a grand gesture! As long as its from the heart…right?

All of a sudden, you feel the weight of the world on your shoulders. A million "what ifs" flood your mind. You think - lightening the burden is as easy as brushing it off and telling yourself it will come naturally. But not everything comes naturally. If you expect a perfect proposal to unfold on its own, like magic, you leave yourself at risk for a big disappointment.

We'll take a closer look at how that went for other newly engaged couples…

Bruce and Linda

They had been weathering life together, enjoying a network of supportive colleagues as they socialized and worked. They enjoyed planned vacations from the daily grind. The next trip planned was Disneyland, California. Bruce decided he would propose here to fulfill his own dream of a Disney proposal. He was overcome with emotion. Head in the clouds and eyes full of dreams as the moment arrived, he couldn't wait anymore. He got down on one knee in front of a large crowd of people, presenting Linda with an open ring box. She was surprised… and a little embarrassed… The crowd of onlookers snapped dozens of photos and cheered for the couple as Linda quickly took the ring and said, “Yes!” They hugged and kissed as she put the ring on.

Suddenly, Bruce wondered “wait, was I supposed to actually put the ring on her finger? But he said nothing and instead smiled as Linda took his hand, trying to walk them away from the crowd. But several people were buzzing around Linda offering to airdrop their photos to her. She quietly wondered to herself that it would have been nicer to have a photographer take “nice pictures” of the two of them, instead of having to share the moment with a bunch of strangers.

Linda took a breath and leaned into Bruce as they let the emotion of the moment simmer, when they both suddenly noticed a very ripe smell. They turned to see an overflowing dumpster on their right, baking in the heat of the California summer. At the same time, a sticky toddler began to scream. Neither one of them was prepared to acknowledge it, as they wandered off to get to a more pleasant spot, but in the back of their minds they pushed away a quiet whisper that said, “for better or worse, we will always remember this moment.”

Elena and Drake

High school sweethearts Elena and Drake held onto their love despite living long distance for many years. Life took them down different paths for a while, but they hoped to reunite after Elena finished her degree.

Drake decided he wanted to surprise Elena with a restaurant proposal during his long awaited trip out to see her on the West Coast. Because he was visiting, he had no real layout of the landmarks or venues but went with the reviews online for a restaurant. Elena and Drake arrived at a dimly lit, romantic restaurant. Sparks were flying as they held hands and tasted delicious food.

While they reminisced over their time together since high school, the restaurant suddenly went silent. Suddenly, Elena and Drake were forced to witness another elegant couple at the table right next to them express their love in a loud and public proposal. Drake’s heart sank… Elena lost her appetite. They both tried to ignore the change in energy and carry on with their evening. The couple left the restaurant with the ring still firmly in the bottom of Drake’s pocket. Elena was left to wonder if Drake would ever propose to her, which led to catastrophizing thoughts which distracted her, not only from dinner, but from the rest of Drake’s trip.

This proposal story makes me CRINGE. I can recall seeing another one recently circulating on social media where the guy proposed to his partner at the zoo, when she’s in the middle of feeding the giraffes. While handing the giraffes lettuce leaves, she turns away from the giraffes to find him down on one knee. The photographer (kudos for arranging a professional!) captures “that” look of surprise and joy in her face. But… in every single picture, this poor girl is holding… you guessed it….LETTUCE!!!

Ok, ENOUGH with the awkward proposals!

There's a little fork in the road that can easily be overlooked at the sacred moment when you place the ring on your partner's finger, with the intention of creating the atmosphere that reflects you both as a couple. One path; a lot of overlooked details which can lessen the experience or even cause it to fail. The other path; an experienced proposal coordinator takes care of all the details to ensure the memory and the experience are flawless.

Friends and family may offer to help, but without any more practice or exposure than you, it can further complicate the proposal by mixing emotion with inexperience.

Say your partner wants a sunset proposal, on the beach and you “think” you’ve picked a perfect spot with the help of a good friend. As a professional, I would wonder;

  • Did they check the tide schedule?

  • Have they been monitoring the weather? We would double check for changes in the forecast.

  • Did they get the exact sunset time?

  • Do they know the best path from the parking lot to the proposal set so the partner doesn’t see it until the last minute?

  • Is the path clear, without dangerous debris or holes in the trail?

  • Is it crowded with spectators who will interrupt your special moment?

The last thing you need is to have your moment spoiled by a sprained ankle or an unexpected wave washing away your decorations.

Let’s look at some couples who DID seek the help of a proposal planner!

The story of Elena and Drake does in fact have a happy ending. After the first disappointing attempt, Drake ended up seeking professional assistance when he found social media posts for a local proposal planner. This company plans and designs proposals by theme and assists with identifying the perfect location. Drake was given theme options and was able to choose one that suited Elena’s style perfectly. They discussed the desired ambience. Sunset time was discussed and the perfect coastal location was identified; a cliff top view of the ocean, away from the mess of the actual sand.

The agreement was for a theme with a wispy curtain elegantly draped at an angle to the side, accented delicately with a floral arrangement and crystals hanging down in front of the ocean view. It was the perfect time of day for a calm, glassy ocean topped with a yellow sun trail. Elena cried with shock and surprise. They drank champagne from golden glasses and their personalized playlist danced in the air around them. A professional photographer captured the moment without interrupting. The Proposal Planner flitted in and out like a hummingbird, collecting bags and jackets when the couple was overwhelmed, keeping them out of the photos…. NO lettuce in sight! Drake breathed a sigh of relief.

Using professionals to set up and help plan your proposal can truly lighten the burden and make dreams come true at that crucial turning of the page. Let a professional mentor guide you while you write your next chapter.


As San Diego’s premiere Proposal Planner, Proposals of San Diego creates moments that reflect the unique love story of each couple. We offer all-inclusive proposal packages, and plan one-of-a-kind experiences for marriage proposals, vow renewals and anniversaries.

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