A Sunset Cliffs Surprise Proposal in San Diego, California: Ash & Megan's Story
There's a very specific kind of chaos that comes with planning a surprise proposal for someone who always figures things out. If you know, you know. Ash knew she’d have to pull out all the stops to keep this secret from Megan. It took a couple months of careful planning, a whole lot of texting under a fake contact name, and one seriously well-hidden ring.
The Story Behind the Surprise
Ash and Megan met on Hinge back in 2023 (proof that the apps canwork if the algorithm is feeling generous), and three years, two cats, and one mini Aussie later, Ash was ready to make it official. They currently call LA home, but San Diego has been calling their name. What better place to propose than the place they are going to start a new chapter, continue building their dream lives, and grow their family?
Sunset Cliffs was the obvious answer. Ash had seen another proposal I'd photographed there and fell in love with the views (what’s not to love?!) and my signature picnic setup. We talked through logistics, and I pointed her toward the southern stretch of the cliffs — it's a little less trafficked than the main lookout points, which meant we could find a spot that felt private and intimate even though we were still very much in one of San Diego's most popular sunset destinations.
Megan told Ash she wanted a surprise proposal and a secret photographer, which — if you've ever tried to keep a surprise from a partner who reads you like a book — is not easy. Ash pulled off some genuinely elite-level secret-agent moves to make it happen:
Saved my number under her best friend's name so nothing looked suspicious in her texts.
Started planning a full month ahead of their anniversary, so it happened earlier than Megan might have assumed.
Shared her location with me directly instead of having to be glued to her phone.
Hid the ring in a cigarette box in her pocket — an incredibly genius idea. She even created a custom ring box with the cigarette box’s size in mind so that it would fit inside perfectly.
Lilies, Greens, Blues, and Pinks: The Décor
Megan's current favorite flower is lilies, so that was the anchor of the florals, paired with a color palette of soft greens, blues, and pinks that felt right at home against the golden cliffs and the ocean behind them. I laid out a picnic blanket complete with a bottle of champagne and little bud vases scattered around — enough to feel romantic and intentional without competing with the view.
The Moment Itself
I got there early to set the scene, tucked myself out of sight, and waited. Apparently, Ash and Megan have a running joke where anytime they pass a proposal setup somewhere, Megan turns to Ash and asks, "Oh, is that for me?" Well, this time it was.
When Ash and Megan walked up and Megan saw the picnic laid out along the cliffside, you could see it click for her — and then Ash got down on one knee. A few nearby onlookers admired the moment and started cheering, which is honestly one of my favorite parts of shooting proposals in public spots like this — strangers becoming instant, delighted witnesses to a love story.
After introducing myself to Megan, congratulatory hugs, and allowing them space to take it all in while I captured more candids, we transitioned into ring shots (a ring like that deserves its moment). I captured the cliffs, the ocean, and just the two of them being themselves: the tight embraces, the giggles, and the little moments in between. We closed out the session with a champagne pop that Megan absolutely crushed — no hesitation, no nerves, just pure joy sprayed across a golden-hour sky.
Once our session wrapped, I gave them their space to watch the sunset together, just the two of them, before they headed off to celebrate over dinner at Starlite, an upscale steakhouse in San Diego for exactly this kind of celebration.
It’s a Small World After All
Okay, this part is too good not to share. When Ash was searching for our emails, she stumbled on an old email from 2018 — the year I moved to San Diego from Colorado. Turns out, we'd been matched on a roommate-search site. Never met, never lived together, no connection… until now. Such a small world!
Thinking About Planning Your Own Surprise Proposal in San Diego?
If you're currently plotting, scheming, hiding rings in creative places, trying to out-smart a partner who notices everything — here's what I'd tell you:
Give yourself time. A month or two out, like Ash did, gives you room to plan the details without rushing.
Ideally pick a location that means something AND that photographs well. Sunset Cliffs is stunning, but it also represented Ash and Megan’s future that they're building together in San Diego.
Don't overthink the décor. A blanket, some flowers in your partner's favorite color palette, and a great view will always shine.
Loop in your photographer early, especially if your partner is the type to catch on fast. Location scouting, timing the light, and coordinating a discreet setup all take a little planning magic behind the scenes.
I'm a San Diego photographer who genuinely loves getting to document love in all its forms, whether it be proposals, elopements, or a casual date on Friday night. If you're dreaming up a proposal of your own in San Diego, anywhere along the California coast, or anywhere in the world, I’m here to help.
Ready to plan your own surprise proposal in San Diego? Reach out here and let's start scheming!
Mallory Kessel Photography is a San Diego-based proposal, engagement, and couples photographer specializing in surprise proposals, intimate elopements, and LGBTQ+ love stories across San Diego, from Sunset Cliffs to Torrey Pines and beyond. Ready to plan yours? Get in touch here.
