Serendipity Sessions: Adam and Kaelyn’s Stranger Photo Shoot Adventure in Portland

Have you ever wondered what it would be like to meet someone for the very first time and instantly pretend you’ve been together forever? Well, that’s exactly what Adam and Kaelyn did during my latest Serendipity Session—a playful experiment in connection, creativity, and storytelling, all captured through my lens.

What Are the Serendipity Sessions?

The Serendipity Sessions were inspired by my winter itchiness—the kind that hits during Portland’s endless gray days when I’m craving something fun and creative. While I didn’t invent the idea of photographing “strangers,” I couldn’t resist putting my own storytelling twist on it. The concept is simple: two strangers meet, step into a "relationship" role, and together, and we (hopefully) craft a narrative through photos that feel intimate, real, and downright authentic. It’s part social experiment, part storytelling, and 100% pure magic.

A little warm-up vogue-ing was necessary, of course.

How It All Began

Adam and Kaelyn responded to my Facebook post calling for adventurous souls to join this experiment. After connecting with them, I knew they’d be the perfect pair. To break the ice, I enlisted my trusty AI sidekick (hi, ChatGPT!) to craft a fun backstory for their shoot:

Storyline: Adam and Kaelyn are a couple who’ve been dating for a short while. They just took their relationship to the next level with a weekend getaway in Portland. They’re exploring the city, soaking in the urban vibes, and embracing both playful and intimate moments together.

With this playful framework in place, we hit the streets of Portland’s Pearl District, ready to turn strangers into a picture-perfect couple.

That moment when you just met but already feel like you’ve known each for…definitely longer than 20 minutes.

Behind the Scenes: From a Little Awkward to A Lot of Awesome

Let’s be honest—things were a tiny bit awkward at first. But who wouldn’t feel that way meeting someone for the first time and then pretending to be smitten?

Kaelyn’s taking in the city vibes while Adam’s got his eyes on the traffic. Safety first, adventure second.

To ease the tension, we added another layer to their “character” roles.

• Adam took on the character of the “serious, be careful, let’s be practical now” boyfriend.

• Kaelyn embraced the “yeah, I’m not any of those things” girlfriend role.

Once they leaned into their parts, the awkwardness melted away, and the session turned into one of pure fun and a “let’s do this!” vibe.

When crossing the street becomes a dramatic performance

I literally laugh out loud everytime I look at this one…

When you take the leap... and Adam’s got you covered

Exploring the Pearl District

The Pearl District was the perfect setting for their faux love story. We started at Tanner Springs Park with its dreamy, urban-meets-natural vibe, wandered through cobblestone streets and hidden courtyards, and had a blast dancing at Jamison Square just as the sun was setting.

We even played around with some motion blur shots to capture that city energy (and let’s be real, to add a little artsy drama).

And talk about timing—after weeks of nonstop rain, we managed to snag a dry afternoon for the shoot—a little cold, but dry. (Coincidentally, the second we wrapped the shoot, the rain came down…hard.)

Just two people, a puddle, and questionable life choices.

Adam had a brief moment of hesitation... but don’t worry, we caught him!

Running through the city, hand in hand, like we’re late for something... but really, just late for nothing

When the twirl leads to the sweetest laugh

Kaelyn’s got other plans and Adam’s just here for the ride—and the safety instructions

Dancing like no one's watching... except for the whole city.

Caution: Twirling can lead to some tangles

Success!

A Sprinkle of Sweetness

Amidst all the laughter and playful banter, Adam and Kaelyn shared moments that would make anyone stop and smile. One of the sweetest highlights came as the chilly air started to creep in. Without hesitation, Adam slipped off his jacket and offered it to Kaelyn—a perfect “boyfriend” move that felt so natural, you’d think they’d known each other for years.

From the way they exchanged soft smiles while walking through Jamison Square to how effortlessly they leaned into their roles as a genuine couple— it was clear these two were fully committed to the story we were crafting. Moments like these remind me that photography isn’t just about capturing what you see—it’s about feeling the connection.

Sometimes, the simplest moments—like a quiet walk—are the ones that stay with you

A Cozy Finish at Lovejoy Bakers

After all the laughter, puddle-jumping, and exploring, we wrapped up our session with a warm and inviting stop at Lovejoy Bakers on NW 10th Avenue. The vibe inside was everything you’d expect from a quintessential Portland bakery—the staff was super friendly, and inside was laid-back, cool, and buzzing with the perfect mix of locals and visitors. Adam and Kaelyn enjoyed some hot cocoa and a vanilla steamer while we all took a moment to relax and chat.

Proof that the best conversations happen over warm drinks and cozy corners

I mean… is it even a photo shoot if you can't sneak in a little product placement?

Wrapping up a shoot, but not the good vibes. Here's to new friends and spontaneous moments.

Want to Be Part of the Next Serendipity Session?

I’m already planning more Serendipity Sessions, and I’d love to hear from you! If you’re someone who loves trying new things, meeting new people, and doesn’t mind a little adventure, click the “Apply Here” button below to fill out the form.

These sessions aren’t just about photos—they’re about creating stories, laughter, and taking a little leap of faith. What else do you have to do on these rainy Portland days?

Capture Your Love Story: The Ultimate Couples Photography Experience

If the Serendipity Sessions sparked your curiosity, imagine the magic we could create with your story—one that’s beautifully, authentically yours. Whether you're celebrating a new chapter, marking years of shared adventures, or simply cherishing the everyday moments that make your relationship unique, this is the perfect time to capture the essence of you two.

What makes your bond special? Is it the way you laugh together, the quiet moments that speak volumes, or the adventures that define your connection? Maybe you want to document this stage of life—a love that’s growing, evolving, and worth remembering forever.

With a full planning session to align every detail with your vision and professional hair and makeup to ensure you look and feel your best, we’ll create something unforgettable. Let’s commemorate your love in a way that’s playful, intimate, and uniquely tailored to you.

Are you ready to capture your story? Fill out my contact form, and let’s start planning!

Love, Laughter, and Roller Skates: A Valentine's Day Shoot to Remember

I don’t know why, but every year about this time I start getting itchy to do something more creative with my shoots. Maybe it’s the dreary Portland weather, but I was craving an adventurous shoot with color. For the past few years, I’ve watched couples do these “Thrift Store Challenges” on Tik Tok, and I decided what better way to celebrate Valentine’s Day this year than by using the concept as inspiration for a new photo shoot experience.

So, I posted about my idea online and almost immediately the perfect couple appeared. Patience and Kyran were up for anything, and boy, did they deliver!

We decided to kick things off with a thrift store outfit challenge where they had to find the perfect outfits for each other in Red and Friends, a vintage clothing store in Portland—in just 20 minutes. Talk about a race against time! To make the challenge even more…well, challenging, they each pulled adjectives out of a bag that they had to “apply” to the outfit they were choosing, and ended up with the combo, "Funky" and "Shocking". Let me tell you, it made the choosing process a little bit more complicated but also so fun!

In the end, Kyran went for a bold red pant suit and a killer embellished hat for Patience, while she picked out a funky combo of a red vest, purple sweatpants, and a blue/purple shirt for him. They looked absolutely adorable.

With their thrifted treasures in hand, we hit the streets, exploring Foster Street and soaking in the vibrant atmosphere. And what better way to navigate the city than on roller skates? Kyran was definitely the skating pro and he led the way while Patience, still getting the hang of it, did her best to keep up alongside him.

Massive shoutout to Hesler Villatoro of Hellareels for capturing all the laughs, twirls, and heartwarming moments of the day on video. You're seriously the best!

As I watched Patience and Kyran make the fun and lighthearted memories together, I couldn't help but think about all the other couples who would love to experience something like this. So here's the deal: I'm absolutely thrilled to offer the "Thrift Store" date experience to future couples who are looking to spice things up and do a photo shoot a little different, while creating unforgettable memories. If you're down for some serious fun, hit me up, and let's make magic happen!

Here's to love, laughter, and unforgettable adventures with the ones we adore!

If you’re in Portland, check out Red and Friends Vintage Clothing here

Interested in booking a Thrift Store Date Photo Shoot? Shoot me a message here