What Shooting 5 Surprise Proposals Over Memorial Day Weekend Taught Us
A newly engaged couple shares an emotional moment in Laguna Beach as the groom places the ring on his fiancée’s finger during a sunset surprise proposal overlooking the ocean on Memorial Day weekend.
Last year around this time, Steph and I had just launched Last Minute Photoshoot. We were barely getting traffic to the site — maybe 10–20 unique visitors a month. At the time, it felt exciting just seeing someone land on the homepage.
Memorial Day weekend last year looked completely different for us. We weren’t photographing surprise proposals yet. We packed up the car, brought our 3 pups down to San Diego, explored the coastline, drank coffee near the beach, and talked endlessly about what we hoped this business could eventually become.
Fast forward one year later.
This Memorial Day weekend, we photographed 5 surprise proposals across Southern California in 4 days.
From Joshua Tree… to La Jolla… to Pasadena… to Laguna Beach.
Somewhere between the long drives, hidden ring boxes, late-night edits, lack of sleep, beach parking chaos, carrying arches through crowded parks, and hearing strangers clap after the “yes,” we realized how much life can change in a year when you keep showing up consistently.
What Shooting 5 Surprise Proposals Over Memorial Day Weekend Taught Us reflects how no two proposals are ever the same — different locations, timelines, weather, crowds, and emotions all shape the outcome. The common thread is having a plan that adapts in real time. That’s where we come in: guiding the timing, flow, and details so you can stay focused on the moment instead of managing the pressure behind it.
Plan Your Surprise Proposal
Friday — Joshua Tree at Sunset
The weekend started in the desert.
Driving into Joshua Tree felt surreal. The roads slowly opened up into massive rock formations and warm desert light. The closer we got to golden hour, the more the landscape started glowing orange.
Before every proposal, we arrive early — usually hours early. We test lighting, scout angles, communicate with the client, and mentally walk through the timeline before anything happens.
Standing out there in the desert testing camera settings while the wind picked up slightly, it hit us again how wild this job really is. Someone trusted us to capture one of the biggest moments of their life in the middle of the desert.
That never gets old.
By the time the proposal happened, the entire sky had softened into warm gold tones. Quiet. Calm. Just the sound of wind moving through the desert and two people stepping into a completely new chapter of their lives.
Saturday Morning — La Jolla Cove
A few hours of sleep later, alarms started going off before sunrise.
Coffee in hand, camera batteries charging in the car, memory cards cleared from the night before, we drove into La Jolla for a morning proposal at the cove.
The energy shift from Joshua Tree to La Jolla was massive.
The sound of waves crashing against the cliffs. Sea lions barking in the distance. Tourists walking the coastline early in the morning. Marine layer hanging over the ocean.
Proposal photography teaches you how quickly environments can change — and how important it is to adapt calmly.
After the proposal, we spent part of the afternoon meeting another client visiting from Oakland for a proposal walkthrough. We walked the location together, talked through nerves, cover stories, proposal positioning, lighting, timing, backup plans, and every small detail leading up to the moment.
That preparation matters more than people realize.
Saturday Sunset — Gliderport in La Jolla
By sunset, we were carrying pieces of our Signature Yes setup through Gliderport while paragliders floated overhead.
Camera bags. Floral pieces. Candles. Tripods. Sandbags.
At times our car looked more like a mobile production van than a normal vehicle.
Holiday weekends add another layer of complexity to proposal photography. Parking becomes difficult. Beaches become crowded. Wind becomes unpredictable. Timelines tighten.
At one point we were holding florals down with one hand while checking lighting conditions with the other.
But when the proposal actually started, everything slowed down.
The crowds disappeared.
The stress disappeared.
The setup disappeared.
It became about the couple and the moment.
That’s always the goal.
Sunday Morning — The Huntington Library Proposal
Sunday morning came fast.
More coffee. More charging batteries. More loading gear into the car before sunrise.
This proposal at the The Huntington Library was especially memorable because we were operating completely undercover.
Under the guise of a family photoshoot with 3 kids… until it wasn’t.
We arrived early to scout the gardens and eventually found the perfect location inside the rose garden to quietly set up the proposal plan. One of the biggest parts of our job is blending in naturally without drawing attention.
Sometimes that means acting like tourists.
Sometimes it means pretending to photograph landscapes.
Sometimes it means blending into family sessions until the exact moment arrives.
The Huntington Library felt peaceful compared to the pace of the rest of the weekend. Sunlight filtered softly through the gardens, families walked quietly through the pathways, and for a few moments everything slowed down.
Then suddenly the proposal happened.
Shock.
Tears.
Smiles.
Excitement.
And just like that, another unforgettable memory was captured forever.
Memorial Day — Laguna Beach
By Memorial Day itself, exhaustion was definitely starting to hit.
But the second we arrived in Laguna Beach, adrenaline kicked back in.
This proposal involved our Signature Yes arch setup overlooking the ocean at Crescent Bay Park before moving down to the beach afterward for engagement photos at sunset.
Parking? Absolute chaos.
Holiday weekends in Laguna can test your patience quickly. Cars circling nonstop. Packed streets. Crowded overlooks. Tourists everywhere.
We had to drive around multiple times before eventually finding parking.
That’s one of the biggest lessons we’ve learned:
don’t panic when things aren’t immediately going your way.
Take a breath.
Stay patient.
Trust your preparation.
Eventually things usually fall into place.
As sunset approached, the stress melted away almost instantly. The sky turned soft orange and blue, waves crashed below the cliffs, and after the proposal we walked barefoot onto the beach capturing engagement photos as the last bit of sunlight disappeared behind the horizon.
And somehow after all the driving, setup, editing, timelines, parking, stress, and lack of sleep…
We’d do it all over again tomorrow.
What We’ve Learned About Navigating Busy Holiday Proposal Weekends
After photographing 5 proposals over 4 days, here are a few things we’ve learned that help us stay calm and prepared during high-pressure weekends:
Plan Every Detail Ahead of Time
We create timelines for every client and communicate constantly leading up to the proposal day.
We help with:
cover stories
outfit suggestions
proposal timing
self-care prep (hair, nails, etc.)
GPS pins
proposal spot photos
walkthroughs when available
lighting recommendations
backup plans
By the proposal day, our goal is for the client to simply show up and enjoy the moment.
Stay Ready So You Never Have To Get Ready
One thing proposal photography teaches you quickly is that bookings can happen fast.
Several of our Memorial Day proposals came in within a week — some within 48 hours.
Every day we:
charge cameras and flashes
organize memory cards
prep backup gear
keep a full tank of gas
restock setup supplies
prepare the car for travel
In this line of work, preparation is everything.
Arrive Earlier Than You Think You Need To
If a proposal starts at 7 PM, we’ll often arrive around 5 PM.
That gives us time to:
scout the location
adjust for crowds
setup decor
test lighting
communicate with the client
mentally reset before the proposal starts
Rushing creates stress.
Preparation creates confidence.
Parking Requires Patience
Seriously.
Especially during holiday weekends.
Some of our biggest stress points this weekend had nothing to do with photography — it was parking.
But panic never helps.
Breathe.
Stay calm.
Keep circling if needed.
Eventually something opens up.
Visualize The Day Before It Happens
One thing that helps us tremendously is mentally visualizing the proposal before arriving.
Where will the client walk from?
Where will we stand?
How will lighting look?
What happens if crowds are heavy?
What’s the backup plan?
Visualization helps remove anxiety because your brain has already “seen” the scenario before it happens.
Respect The Location
A lot of proposal setups happen in public spaces surrounded by homes, beaches, cliffs, and parks.
We always:
clean up completely
bring trash bags
use a hand rake for beach setups
protect the environment
leave locations cleaner than we found them
Respect matters.
Don’t Transfer Stress To Your Clients
Even if parking is difficult…
Even if setup is delayed…
Even if the beach is crowded…
Clients feed off your energy.
Part of our job is helping people feel calm enough to stay fully present during one of the biggest moments of their lives.
Final Thoughts
A year ago, Steph and I spent Memorial Day weekend walking around San Diego with our pups wondering if this dream would work.
This year we spent Memorial Day weekend photographing 5 surprise proposals across Southern California.
We’re exhausted.
Grateful.
Still processing it all.
There were moments this weekend where we were carrying arches across crowded parks, editing sneak peeks past midnight, waking up before sunrise again, surviving off coffee, trying to find parking near packed beaches, and somehow still smiling before every proposal because we genuinely love what we do.
Proposal photography is beautiful chaos.
And above all else, we’ve learned this:
have fun, smile often, listen more than you speak, stay present, and never take these moments for granted.
If you’re planning a surprise proposal, intimate wedding, or engagement session and want a team that helps guide every detail from beginning to end, we’d love to help.
You can also read more real client experiences and proposal stories here:
