He Flew Her in From Milwaukee and Led Her to the Cliffs — A Sunset Cliffs Surprise Proposal Story
Matthew reached out to us on December 5th with one of those emails you don’t forget. Kind, intentional, and full of trust, he asked if our cliffside boho picnic setup with proposal photography at Sunset Cliffs was still available. Although we were already booked for his original date, we were able to make the following day work — and just like that, the plan was set in motion. Flying in from Milwaukee for only a few days, Matthew wanted everything to feel effortless for Mahak. From timelines and cover stories to her favorite colors, flowers, snacks, and personal details, every part of this Sunset Cliffs surprise proposal was thoughtfully planned. On the day of the proposal, we arrived early, set up the boho picnic overlooking the ocean, and waited quietly as Matthew led Mahak down the cliffs. With waves crashing below, the Pacific stretching endlessly behind them, and cheers echoing from afar, he asked her to marry him — and she said yes. A timeless San Diego proposal moment, captured exactly as it unfolded.
Some inquiries stay with you the moment you read them.
On December 5th, Matthew reached out to us by email. You could feel his energy right away — calm, thoughtful, and genuinely kind. His message started with:
“Hi there, I hope you’re doing well. I’m reaching out to see if the cliffside boho pricing with photography at Sunset Cliffs might still be available on Friday, December 12.”
At the time, we were already on a photoshoot. Steph was snapping away, fully locked in, and in between moments when I wasn’t needed, I replied back. We let Matthew know we were already booked on the 12th, but had availability the following day — Saturday, December 13th.
Without hesitation, he said yes.
He Flew Her in From Milwaukee and Led Her to the Cliffs — A Sunset Cliffs Surprise Proposal Story shows how thoughtful planning turns travel into a once-in-a-lifetime moment. If you’re proposing while visiting San Diego, we’ll help you choose the perfect cliffside spot, time the sunset, and capture the “yes” seamlessly.
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Flying in for a once-in-a-lifetime moment
Matthew and Mahak were flying in from Milwaukee and were only in San Diego for a few short days. This wasn’t just a trip — it was the trip. After a few messages back and forth, we finalized the details and shifted into planning mode.
The days leading up to the proposal were all about intention.
We walked through:
A clear timeline
A believable cover story
And the finer details that turn a proposal into an experience
We asked Matthew about Mahak’s favorite colors, flowers, snacks, and even her favorite board game — something we’ve recently started including in all of our boho picnic setups at no additional charge. Those personal touches matter. They’re what make the moment feel like hers, not staged or generic.
From planning to execution at Sunset Cliffs
As the big day approached, we organized our gear, loaded up the vehicle, and jumped on one final call with Matthew to walk through everything one last time. At that point, all that was left to do was show up.
Sunset Cliffs never disappoints.
We arrived early at one of our go-to cliffside locations, set up the boho picnic overlooking the ocean, and waited. When Matthew and Mahak were dropped off by their Uber, I kept my eyes on them from a distance — partly to make sure they didn’t get lost, partly to make sure we stayed completely undercover.
I tried flagging Matthew down a couple of times without being spotted… unsuccessfully 😂
Eventually, we made eye contact.
From there, I quietly led Matthew down toward the picnic setup while Mahak followed, completely unaware of what was waiting for her.
The proposal moment
As they reached the setup, Matthew took a deep breath and asked Mahak to marry him.
Waves crashed against the cliffs below. The ocean stretched endlessly behind them. People watching from a distance began cheering as she said yes.
It was one of those moments where everything aligns — the location, the timing, the emotion. Pure joy. No rushing. No distractions. Just two people and the beginning of their next chapter.
Why Sunset Cliffs is perfect for a surprise proposal
Sunset Cliffs is one of our favorite locations for surprise proposals in San Diego for a reason. It offers dramatic coastal views, natural sound from the ocean, and space to create an intimate moment even when others are nearby. Pair that with a boho picnic setup and mini proposal photography, and you get something that feels elevated, personal, and timeless.
Final thoughts
Matthew trusted us completely — and that trust is something we never take lightly. From planning to execution, this proposal was about creating a moment that felt effortless, intentional, and true to them.
If you’re planning a Sunset Cliffs surprise proposal and want more than just photos — something thoughtful, calm, and beautifully handled — we’d love to help you bring it to life.
Because the best proposals don’t feel staged.
They feel meant to happen.