New Orleans Surprise Proposal and Engagement Photography

Tony and Ashley’s zany French Quarter Courtyard Proposal and City Park Engagement Session

Some New Orleans Surprise Proposals go completely according to plan. And some New Orleans Surprise Proposals are Tony and Ashley’s. Even though things were a bit all over the place, everyone involved was still ecstatic. And that’s kind of the thing about surprise proposals- they’re either perfect or perfectly imperfect and still wonderful every time.

Tony contacted me months before his trip to New Orleans. He was planning on visiting with his girlfriend, Ashley, and 20 or so of their friends for her 30th birthday. I learned a really valuable lesson on this one- never start planning too early. There are entirely too many variables in this post-Covid world. Far too many things can change over the course of a few months and a plan could need to be re-worked months down the line. Which is exactly what happened for Tony. We worked out a plan with a restaurant on the edge of Jackson Square. We hired a band and were going to surprise Ashley by having Tony sneak out of the restaurant, sending in the band leader in to fetch Ashley, and have her come outside to find the band, both of their parents, and Tony on one knee.

But then it turned out the restaurant was only willing to offer their large party a pre-fix menu and wouldn’t include a vegetarian option for the handful of vegetarian guests. UGH! So it was back to the drawing board. To complicate things, Covid was popping off again so it was important to find a place with courtyard seating for a lot of guests.

I sent Tony a lot of suggestions and he ended up finding what he needed at the Creole Cookery. He decided to nix the band as things continued to change and evolve and we were no longer at a location with somewhere cute to stroll to outside. But we met again a few weeks before their trip and figured out what we would do. I was going to come in and hang out at the bar in the courtyard while Tony, Ashley, and their friends enjoyed some pre-dinner cocktails. After they were settled, Tony and Ashley’s parents were going to come into the courtyard and surprise her (she didn’t know they were going to be there!). While Ashley was distracted by the parents, Tony would get down on one knee behind her and her mom would tell her to turn around. I went to the restaurant several days before the proposal and spoke with the manager. He agreed to move a few tables to make room for Tony’s proposal and showed me how their party’s tables would be set up so I could tell Tony exactly where to stand.

Every now and then there is one client who just has everything go haywire. Things can go flawlessly with countless couples and one guy just gets all the complications. It seemed that poor Tony was that guy. When he arrived at the restaurant, things weren’t as they were supposed to be. I told him not to worry, that I was on my way, and we would figure it out. We worked out a new plan just as Ashley was arriving at the restaurant and I went and took my seat at the bar to wait for the parents’ arrival. I had also met Ashley’s mom via zoom to clue her in on the whole plan so she was keeping me up to date on what was going on with the other parents… and the other parents were very, very late. An hour went by and I watched as the twilight-lit courtyard grew darker and darker, leaving only the overhead string lights and color-changing LEDs in the fountain as light for the proposal.

Crap.

I know my way around low-light. I cut my teeth photographing live music in dimly-lit French Quarter music venues. I’ve photographed my fair share of weddings with next-to-no light (once the ceremony ran so late I photographed the kiss under the moon!). So I knew that I’d be able to get the shot even if the light wasn’t the prettiest. But it was a sticky night and our couple was being offered many birthday drinks before dinner (they were waiting to order until the parental surprise). I was afraid things might get a bit sloppy! If things were sloppy, though, no one was the wiser.

When all of the parents finally made it, the courtyard erupted in joyful screams. I watched Tony nervously take a few steps back and try to get Ashley’s attention. She eventually turned around and instantly knew what he was planning even though he hadn’t taken a knee yet. He starts on his speech and I start firing away. Ashley’s scream-laugh-cry reaction was definitely one of a kind! She said yes and the entire group encircled the happy couple. When she realized I was there photographing, she threw her arms around me and thanked me for being there. I only just met her and in that moment I had a feeling I was going to know this woman for years to come.

Tony and I had planned on doing their engagement portraits the next day. It was late August and far too hot to be taking portraits after getting sweaty in a courtyard. Plus the timing wasn’t right for light. We got together at City Park the next day and I got to spend a bit of time getting to know Ashley as well after working with Tony for months. I absolutely loved the way they interacted- they were goofy, weird, irreverent, and also very much in love. My sense of humor blended in perfectly with theirs and it was a very memorable shoot.

A week later, I found myself on an unexpected overnight layover in Denver where Tony and Ashley live. So I gave Tony a shout and asked him if they’d like to grab dinner. He was working but he tossed me Ashley’s number and she was over the moon to meet up. I was even travelling with my assistant from her engagement session so it was one happy reunion. Ashley is such a doll she drove clean out to the airport to pick us up. I had the best time chatting with her until we had to leave to catch a train back. I definitely left Denver with a new friend.

Even though things didn’t go according to plan, everything was exactly right. The zaniness of the proposal was totally on brand for Tony and Ashley. It was just the right amount of extra. Something tells me I’ll be back in Denver for a wedding next year. Maybe not as a photographer. Maybe as a guest.

Want to plan your own zany Surprise Proposal?

Enjoy this selection of Tony and Ashley’s French Quarter Surprise Proposal and City Park Engagement Photography session.