Jeffrey Vallis is a freelance writer and communications specialist living in Toronto.

Thoughts and reflections on my life and work.

Thoughts and reflections on my life and work.

Best laid plans... when proposals go awry

Remember the scene in The Wedding Singer where Adam Sandler’s character serenades Drew Barrymore’s character over the PA system on a flight and then proposes to her? It’s a picture perfect proposal. In real life, however, you can plan, prepare and rehearse, and still somehow it goes off script. 

Chris intended to propose to me at the peak of the dormant volcano Mauna Kea, the highest point on Hawaii. We would watch the sunset at 6:09 p.m. from above the clouds and stay for the free stargazing at one of the best sites in the world for astronomical observation. Then, he would go into a gushy speech about being on top of the world together, and how I make him feel like he’s on top of the world all the time and he would propose to me right there, 9,200ft (2,800m) above sea level.

Shoulda. Coulda. Woulda.

The visitor information station was overcast and rainy when we arrived, and it was snowing and hailing at the peak. With no backup plan, he decided to propose a few days later over Thai takeout and grocery store wine in our secluded jungle hut. It had been a long and stressful day and he was determined to turn things around for the better. And it worked!

In sharing our story with friends and family, we realized that a lot of people shared the not-so-perfect proposal experience.

My cousin Leanne was caught off guard by a surprise proposal on a boat ride she didn’t want to go on. Dustin pretended the boat broke down and Leanne got mad that they didn’t bring anyone with them who could have helped. That’s when he proposed.

Her sister Lindsay was in San Francisco on an oddly hot weekend in December. Ryan refused to take off his jacket and Lindsay wouldn’t let it go, even offering to hold it for him. He proposed earlier than he planned, afraid the ring would fall out if he took off the jacket.

My friend Robyn’s boyfriend’s proposal plan went out the window when the engagement ring didn't arrive in time. Doug planned to put the ring in an empty kitchen cupboard on the weekend they were moving out of their condo and ask Robyn to check the cupboards one last time, where she’d find the ring. No such luck.

For my friend Courtney, her husband had every intention to propose at Thanksgiving dinner when it was his turn to say what he was thankful for (with a sappy speech like something out of Love Actually). Instead, he panicked before dinner and said “You forgot something,” before presenting her with the ring. She’s not entirely sure that he ever even said “Will you marry me?”

Even my dad’s proposal to my mom got botched when my cousin Tracy (four years old at the time) blew the surprise by asking my mom, “Do you like the ring Uncle Bobby got you?” hours before my dad was to propose.   

Share your proposal story—perfect or otherwise—in the comments below.