Engagement

A Playful and Chic Engagement Session at Monserate Winery

January 6, 2025

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A Playful and Chic Engagement Session at Monserate Winery

After getting to know Elena and Dillon, it became clear that a playful and chic engagement session at Monserate Winery was the perfect way to best tell their love story. As a wedding photographer, I believe that capturing authentic moments is key. That’s why I cherish the opportunity to get to know my couples before their big day. Learning about their unique love story, their individual personalities, and their vision for their wedding allows me to create images that truly reflect who they are as a couple. By building a rapport and fostering a comfortable environment, I aim to ensure that when their wedding day arrives, any nervousness or discomfort fades away. Instead, they can fully embrace the excitement and emotion of the day, allowing their true selves to shine through in every photograph. My connection with Elena and Dillon was immediate. Their genuine and warm personalities resonated with me deeply, and I knew we would be a great team. Finding a photographer you connect with on a personal level is crucial. It ensures a relaxed and enjoyable experience, allowing you to truly be yourselves throughout the day.  Enjoy meeting Elena and Dillon!

Meet Elena and Dillon

Dillon and I have been together for nearly six years, and we’re currently planning our 2025 wedding. We actually went to the same high school, but our paths didn’t cross until Dillon’s final year of college. I was sorority sisters with his cousin Amanda, and I’d occasionally pop into their FaceTime calls… let’s just say I found a way to subtly flirt with Dillon during those calls.  Those playful moments eventually led to our first date at Badass Coffee, just down the street from our high school in San Diego – the city where we both grew up. And the rest, as they say, is history!

Our Vibe: Loving, Supportive, Grounded

As a couple, we prioritize family and commitment. We’ve been fortunate to have strong examples of these values throughout our lives, and our shared faith plays a significant role in guiding our decisions. We complement each other well – we’re a great team, always offering support and encouragement. Our friends and family would say we bring out the best in each other. We both love staying active, whether it’s hitting the gym, snowboarding in Colorado, or enjoying an adventurous hike. We’re also driven individuals with a passion for intellectual pursuits and career growth. And of course, we share a love for music, dogs, and countless TV shows and movies.

Our Engagement Photo Vision: A Touch of Tuscany and Chic Fashion

Choosing Monserate Winery for our engagement session was a no-brainer. We actually toured it while searching for our wedding venue, and though we ultimately chose a different location, we were completely captivated by the stunning views, gorgeous water features, and unique Italian architecture. When Tiffany suggested Monserate, it immediately felt perfect! The elegance and romance of the estate would perfectly complement the look and feel of our wedding. And as a huge Taylor Swift fan, I couldn’t resist the opportunity to recreate some of those iconic “Love Story” moments on the estate’s beautiful stairs and balcony. For our engagement photos, we wanted to have fun with our style while still feeling authentically ourselves. Since our proposal photoshoot was more casual and on the beach, we wanted to contrast that with a more formal look for Monserate. For our first look, I chose a long fitted dress, and Dillon opted for a sharp black suit. We wanted to channel some classic Hollywood glamour while still feeling comfortable and confident.

I always feel most like myself with my hair down in curls, so that was a must. Dillon went with his classic gelled, brushed over fade. For makeup, I opted for a “natural glam” look – something that would enhance my features while still feeling authentically me.

What We’re Most Excited About Leading Up to Your Wedding Day

We’re most excited about celebrating this important milestone with all of our loved ones. We can’t wait to embark on this exciting new chapter together!

Choosing Our Photographer: Tiffany

Choosing our wedding photographer was a crucial decision. We explored countless options, relying on recommendations from our wedding planner and extensive research online. Customer reviews were also a major factor in our decision-making process. We were drawn to Tiffany’s work because of her crisp photos, timeless editing style, and genuine professionalism. We had narrowed down our options to a few finalists, but after our initial call with Tiffany, we knew she was the perfect fit. Her approach and personality were incredibly genuine and we immediately felt a connection.

Groom embraces his bride to be on the balcony of Tuscan style wedding venue, Monserate Winery's Tuscan Estate during their engagement photos.

Lush vines trail down the staircase railing at Tuscan style wedding venue, Monserate Winery's Tuscan Estate as groom to be pulls his bride to be close and kisses her forehead. Fiance's hold hands as they walk through the courtyard of the Tuscan Estate at Monserate Winery, a Tuscan style wedding venue in Southern California.

Fiances snuggle into each other as they share a slow dance in the courtyard of Villa De Fiore at Monserate Winery, a stunning Tuscan style wedding venue in Fallbrook, CA.

Bride and Groom to be embrace in the vineyards at Monserate Winery - the premier vineyard wedding venue in Southern California. Groom-to-be stands behind his bride to be and holds her close as they share a sweet moment of laughter during their engagement session at Monserate Winery - one of the top Vineyard wedding venues in SoCal.

Groom-to-be looks adoringly at his fiance to be under a beautiful brick archway at Villa De Fiore - a Tuscan style wedding venue at Monserate Winery in Fallbrook, CA.

Monserate Winery is the most beautiful Tuscan style wedding venue in Southern California.  Whatever you're envisioning for your big day, a vineyard style wedding venue, lake style wedding venue or garden style wedding venue, this place has it all.

Groom-to-be wears a black suit and white button down as he twirls his fiance to be in a stunning white, one-shouldered gown with a bow and high slit during their engagement session at Tuscan style wedding venue, Monserate Winery in Southern California.

Bride-to-be wearing a long white gown with a large bow on one shoulder smiles as her groom-to-be gives her a kiss on the cheek during their playful engagement session in the courtyard of Villa De Fiore a Tuscan style wedding venue at Monserate Winery in Fallbrook, CA.

Bride and groom to be hold hands as they gaze into each other's eyes, framed by a beautiful, architectural, brick archway at Tuscan style wedding venue, Villa De Fiore at Monserate Winery.

Groom-to-be lifts his bride-to-be and spins her around as they share a kiss during their playful engagement session at Tuscan style wedding venue, Villa De Fiore at Monserate Winery in Southern California.

Brunette male in a black suit kisses his fiance, a brunette female in a white, fitted, one shouldered dress during their playful and chic engagement session at Monserate Winery with Tiffany J Photography. Playful engagement photos at Monserate Winery as bride-to-be spins into her groom to be.

Groom-to-be leads his bride-to-be across the beautiful courtyard at Monserate Winery during their engagement session.

Chic and modern detail photo showcasing bride-to-be's ring, bracelet and shoulder bow on her white dress, while their faces are slightly cropped out of the frame.

Bride-to-be stands on a balcony looking down at her groom-to-be.

Playful engagement photo of man dipping and kissing his bride to be during their engagement session at Monserate Winery.

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About Tiffany

From the delicate details, to the fleeting moments, to the candid expressions, my number one priority as your wedding photographer is to create imagery that takes you right back to how you felt in that exact moment.

Through intentional composition, I strive to zero in on the moments you likely didn’t even notice. Memories are so much more than details … they’re feelings. With every click of my shutter, I want to bring your vision to life while allowing you to be deeply present.