05/19/2026
There’s something undeniably magical about an overcast day in Malibu. While most people hope for bright sunshine, photographers know the truth — soft cloud cover creates the dreamiest light imaginable. No harsh shadows, no squinty eyes, just perfectly even light that allows us to shoot effortlessly from every angle. Jenna and Benny’s engagement session at Point Dume was the perfect example of how a chilly gray evening can turn into pure photographic magic.
We met at The Sunset Restaurant before making our way toward the breathtaking overlook at Point Dume. The ocean breeze was crisp, the waves crashed below the cliffs, and the moody skies wrapped the coastline in the most romantic atmosphere. Malibu has a way of making every love story feel cinematic, and Jenna and Benny’s story fit perfectly into the landscape.
These two first met back in Chicago five years ago after connecting on Hinge during the summer of 2021. Both were home after finishing their freshman year of college, and what started as a summer romance quickly became something much deeper. After an unforgettable summer together, they headed back to school and spent the next three years navigating long distance — proving that distance truly means nothing when two people are meant to be together.
Eventually, Benny began pursuing his PhD at University of Southern California, and Jenna made the leap to California to begin building their future together. Their love story already felt like something out of a movie, but Benny somehow managed to make the proposal even more unforgettable. Surrounded by roses, he sat down at the piano, played John Legend’s “All of Me,” and sang to Jenna while tickling the ivory keys in a room filled with romance. It was the kind of proposal every girl dreams about.
When they reached out to me about photographing their engagement session, we immediately knew California had to be part of their story. Although they’ll be heading back to Chicago next summer for their wedding, Malibu became the perfect backdrop to capture this chapter of their lives together — the season where their long-distance journey turned into forever.
Throughout the session, Jenna and Benny laughed, held each other close against the cool ocean breeze, and completely forgot the camera was even there. Those are always my favorite moments to capture — the in-between glances, the genuine smiles, and the quiet little moments that say everything without words.
As the fog rolled over the cliffs and the sun softly disappeared behind the moutains, I couldn’t help but feel so excited for what’s ahead for these two. Their story is one of patience, commitment, adventure, and unwavering love — and next summer, I’ll have the honor of documenting the moment they finally say “I do” back in Chicago.
Jenna and Benny, thank you for trusting me to capture such a beautiful season of your lives. Malibu gave us the dreamiest backdrop, but the love you share is what truly made this session unforgettable.https://www.naomiepsteinphotography.com/blog/jennabennymalibuengagement
