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Engagement

A Rain-Soaked Surprise Proposal: Ann & Reid’s Engagement Story

November 6, 2025

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Charleston surprise proposal in the rain

Operation Hansen: The Perfect Plan

Reid spent nearly a year planning the perfect proposal for Ann, one filled with meaning, surprise, and family. Every detail mattered to him, from the setting to the story that would make it all believable. He wanted the moment to feel effortless for Ann, something that fit naturally into their lives but still carried all the weight and wonder of forever.

To keep everything a secret, Reid created a cover story so thoughtful that not even the most suspicious fiancée could have guessed what was coming. He told Ann that his boss had planned a client trip that week but had to cancel at the last minute. The trip, along with its “client experience,” was generously offered to Reid and Ann instead, complete with dinner at Bluff Charleston, a private residence on Isle of Palms.

The Best Kept Secret

As part of that “experience,” the evening would include a private chef, a beautifully styled tablescape, and a photographer who would be capturing images for the chef’s marketing portfolio. Reid explained that the photos would highlight the food, atmosphere, and guest experience, making the presence of a photographer feel completely natural to Ann.

Ann believed she and Reid were simply “modeling” for a few of the chef’s marketing photos during dinner. In reality, the story was the perfect setup for a surprise proposal that would take her completely off guard.

The dinner that began as a boss’s canceled trip and a client experience, complete with plans for marketing photos, became Reid and Ann’s once-in-a-lifetime evening. What started as a believable story evolved into a night filled with love, surprise, and celebration.

The dream team behind the scenes included Newberry Events for planning and design, Chef Wyatt Gaus, Branch Flower Shop for florals, Stradley Davidson for linens, EventWorks for rentals, and myself, Alisha Cory Photography, there to document every heartfelt moment.

The Weather That Changed Everything

Charleston, however, had other plans. The October air turned chilly and blustery, and rain poured for most of the weekend, making it nearly impossible to photograph outdoors as originally planned. While the couple enjoyed their private dinner inside Bluff Charleston, I was quietly reworking the plan in my head.

Rain on a proposal day can feel like a nightmare, especially after months of preparation. But as photographers, we learn to see the beauty in it. The way candlelight reflects off wet pavement, how overcast skies soften every color, and how intimacy seems to bloom in the shelter of shared umbrellas all create a mood that’s completely unique.

So while Reid and Ann were savoring their meal, I began crafting a new plan to keep the surprise proposal both beautiful and protected from the weather.

After dinner, I asked them to step under the venue’s covered patio for what I told them would be one last “marketing photo” for the chef, a champagne pop to conclude the evening’s shoot.

Charleston surprise proposal in the rain

The plan worked perfectly. As the couple laughed and celebrated with champagne in hand, I asked for just one more photo, then another, slowly guiding them into position. When the moment was right, I gave the prearranged cue, “belly to belly.”

Reid immediately recognized the phrase. He turned toward Ann, reached for her hands, and dropped to one knee.

Charleston surprise proposal in the rain

It was the kind of quiet that only comes when everything else fades away, rain still dripping softly nearby, a hush in the air, and two people realizing that their forever had just begun.

Capturing a Surprise Proposal in the Rain

Once the initial tears and laughter settled, I asked Ann if she’d like to step outside for a few portraits before it got dark. The rain had finally eased enough to give us a short window of time. We slipped outdoors, careful on the slick steps, and captured a few portraits around Bluff Charleston, about ten minutes of pure joy and disbelief.

Then came the next surprise. As we wrapped up, headlights appeared in the driveway. Ann’s family had arrived in secret, including her grandparents, uncle, and the couple’s beloved dog, Ford.

Ford bounded toward them, tail wagging and eyes bright, as the family surrounded the newly engaged couple in celebration. The cheers, the laughter, the happy tears—it was the perfect ending to a surprise proposal that began with uncertainty and ended in warmth, joy, and love.

Tips for a Rainy Proposal

If you’re planning a surprise proposal in Charleston or any outdoor setting, here’s a little advice inspired by Reid and Ann’s story:

  1. Always have a Plan B. Whether it’s a covered patio, a porch, or an indoor space with good light, identify a rain-safe location ahead of time.
  2. Embrace the weather. Overcast skies make for stunning, romantic light. A clear umbrella can even add to the aesthetic.
  3. Communicate with your photographer. A great proposal photographer can adjust on the fly, keeping your moment stress-free and beautiful.
  4. Don’t let rain dampen your excitement. Sometimes, unexpected weather adds to the story, making it even more memorable.

A Charleston Engagement Session (Take Two)

Because of the stormy proposal night, we planned a follow-up engagement session in downtown Charleston the following week. This time, the weather was completely on our side.

Reid, Ann, and I wandered Charleston’s cobblestone streets — with Ford trotting happily beside us, of course. Ford, their Newfoundland-poodle mix, is named after Reid’s favorite Ford truck and is every bit as loyal and full of personality. He soaked up the attention, posed like a pro, and was treated to plenty of snacks between shots.

Our walk took us past pastel facades, wrought-iron gates, and quiet courtyards that shimmered in the afternoon light. We ended at Hibernian Hall, where Ford claimed a cool patch of floor as his resting spot while we wrapped up the shoot.

About the Couple

During our downtown session, I learned that Ann is a first-grade teacher and Reid is an attorney. The two met through Ann’s brother, who also happens to be one of Reid’s closest friends. What started as friendly double dinners soon turned into, “Maybe we should hang out without your brother.” The rest, as they say, is history.

The couple is down-to-earth, kind, and completely devoted to each other and to Ford. Their love story has a joyful ease to it, much like a Charleston evening after the rain.

Final Thoughts

From a candlelit dinner and a champagne-popping surprise proposal to a downtown engagement session with their beloved dog, Reid and Ann’s story captures everything that makes Charleston such a timeless setting for love stories. It’s a city full of beauty, surprises, and an ability to turn even a rainy night into something unforgettable.

Whether you’re dreaming up your own surprise proposal or planning a Charleston engagement session, remember this: every moment, rain or shine, tells part of your story. 

And I’d love to help you capture it.

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