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Engagements

This Downtown San Antonio Engagement Session Feels Like Watching a Meet-Cute

May 10, 2024

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Set against the bustling urban backdrop of The Pearl in San Antonio, Kayli and Sean’s engagement session was nothing short of magical. Their love story unfolded amidst the eclectic charm of this historic district, offering a vibrant mix of contemporary and rustic settings that mirrored the lively spirit of their relationship. Because the area is so beautiful, I’ve photographed there many times, but this session was my all-time favorite.

A photo of an engaged couple sitting together inside of a coffee shop. The image is focused on their lattes as the couple talks and holds hands. The photo was taken through a window from the outside of the coffee shop.

The session kicked off with laughter echoing down the avenues as Kayli and Sean playfully navigated the historic streets. The urban setting, with its stunning blend of old and new architecture, provided a perfect canvas for their love. Kayli’s laughter was contagious, sparking joy in every frame, while Sean’s adoring glances said it all.

A photo of a man and a woman walking across a crosswalk in downtown San Antonio. The woman is wearing a white dress and white heels and the man is wearing a white button-up and khaki pants.
A monochrome motion-blur image of a couple jumping up onto a curb after crossing the street. The photo only shows them from the waist down.

As we ventured deeper into The Pearl, every corner and cobblestone street seemed to celebrate Kayli and Sean. Their spontaneity brought the scene to life, creating a perfect balance of romantic serenity and vibrant urban energy. We paused in front of the iconic Cured building to create a few images with an editorial feel.

A man and a woman walking together lovingly next to the shops at the Pearl in San Antonio. The couple is looking at each other.
A monochrome photo of a man and a woman looking at eachother. The woman is leaning up against a brick wall, and the man is leaning over her, with his hand on her waist.
A photo of an engaged couple in San Antonio. The woman has her back against a brick wall, and has her hand positioned on the man's stomach. The man is kissing the woman's cheek as she smiles.
A monochrome photograph taken on film of an engaged couple. The man is leaning the woman against a brick wall and holding her waist.
A photo of an engaged couple standing together. The woman is turned in towards the man slightly, and has her hand rested on his shoulder. The photo only shows their torsos.
A monochrome film photograph of a man and a woman standing in front of a brick building. The man is looking down at the woman as she lovingly looks up at him while placing a hand on his chest.
A man and a woman outside of the Cured building in San Antonio. The man is sitting on the steps while the woman is standing next to him. The man is resting his head against her hips.
A man and a woman outside of the Cured building in San Antonio. The man is lifting the woman in the air as they look at each other, and the woman is kicking up one of her legs.

I noticed a cute café on a corner, and Kayli and Sean wandered in to order a pair of lattés. The moment felt like watching a meet-cute unfold, and the images reflect the authentic, genuine love that they have for each other. I took a few images from outside of the cafe, then Kayli and Sean cuddled up at one of the outdoor patio tables to enjoy their drinks.

A photo of an engaged couple sitting together inside of a coffee shop. The image is focused on their lattes as the couple talks and holds hands. The photo was taken through a window from the outside of the coffee shop.
A monochrome photo of an engaged couple sitting together inside of a coffee shop. The woman is resting her chin on her hand as she lovingly looks at the man, who is telling a story. The photo was taken through a window from the outside of the coffee shop.
A photo of an engaged couple sitting together inside of a coffee shop. The image is focused on their hands, as they hold each other's. The photo was taken through a window from the outside of the coffee shop.
A photo of an engaged couple sitting together inside of a coffee shop. The woman is resting her chin on her hand as she lovingly looks at the man, who is telling a story. The photo was taken through a window from the outside of the coffee shop.
A photo of an engaged couple sitting inside of a coffee shop at a table together. The photo was taken through a window from the outside of the shop. The man and woman are looking at eachother and holding hands.
A photo of an engaged couple sitting together inside of a coffee shop. The image is focused on their lattes as the couple talks. The photo was taken through a window from the outside of the coffee shop.
A photo of an engaged couple sitting inside of a coffee shop at a table together. The photo was taken through a window from the outside of the shop. The man and woman are looking at eachother lovingly. The photo is monochrome.
A monochrome photo of an engaged couple sitting together inside of a coffee shop. The woman is looking down while listening to the man, who is telling a story. The photo was taken through a window from the outside of the coffee shop.
A photo of an engaged couple sitting together inside of a coffee shop. The image shows the couple with two coffees as they hold hands and lovingly look at each other. The photo was taken through a window from the outside of the coffee shop.
A monochrome photo of an engaged couple sitting together inside of a coffee shop. They are both laughing as they look at each other. The photo was taken through a window from the outside of the coffee shop.
A monochrome film photograph of an engaged couple sitting at a patio table. There are two cups of coffee sitting on the table. The man is leaning into the woman and holding her hand.
A man and a woman sitting at a patio table outside of a coffee shop. They are looking at eachother and engaging in conversation. The photo is focused on their feet, from the waist down.
A photo of an engaged couple sitting inside of a coffee shop at a table together. The photo was taken through a window from the outside of the shop. The man and woman are looking at eachother, and the woman is holding his chin while they both hold the handles of their cups.
A man and a woman sitting at a patio table outside of a coffee shop. They are looking at eachother and engaging in conversation.

At the end of our session, Kayli and Sean changed into more casual attire. Then, we headed up to the rooftop of the parking garage. The height of the garage allowed us to capture the gorgeous scenery of the city as this lovely couple frolicked and played, enjoying every moment of their time together.

A man and a woman in a rooftop parking garage in San Antonio. The man is wearing a grey t-shirt and jeans, and the woman is wearing a white shirt and ripped jeans. The woman is sitting on a railing and wrapping her legs around the man, while holding onto his face as they kiss. The man is holding onto her waist.
A man and a woman in a rooftop parking garage in San Antonio. The man is wearing a grey t-shirt and jeans, and the woman is wearing a white shirt and ripped jeans. The photo showcases the scenery of San Antonio. The man is holding the woman around her butt, and is spinning her in a circle. The woman is leaning back slightly.
A man and a woman in a rooftop parking garage in San Antonio. The man is wearing a grey t-shirt and jeans, and the woman is wearing a white shirt and ripped jeans. The couple is engaged in a passionate kiss, and have their hands on each other's faces.
A man and a woman in a rooftop parking garage in San Antonio. The man is wearing a grey t-shirt and jeans, and the woman is wearing a white shirt and ripped jeans. The man is holding the woman on his back, and is supporting her by grasping under her knees. The woman has her arms wrapped loosely around his neck.
A man and a woman in a rooftop parking garage in San Antonio. The man is wearing a grey t-shirt and jeans, and the woman is wearing a white shirt and ripped jeans. The man is holding the woman on his back, and is supporting her by grasping under her knees. The woman has her arms wrapped loosely around his neck. The woman is kissing the man's cheek.
A film photo of an engaged couple in a rooftop parking garage. The background showcases downtown San Antonio. The woman is sitting on a railing, wrapping her legs around the man and her arms around his neck. The man is holding onto her.
A monochrome photo of a man and a woman in a rooftop parking garage in San Antonio. The man is wearing a grey t-shirt and jeans, and the woman is wearing a white shirt and ripped jeans. The man is holding the woman on his back, and is supporting her by grasping under her knees. The woman has her arms wrapped loosely around his neck. The woman is kissing the man's cheek.
A monochrome photo of a man and a woman in a rooftop parking garage in San Antonio. The man is wearing a grey t-shirt and jeans, and the woman is wearing a white shirt and ripped jeans. The man is holding the woman on his back, and is supporting her by grasping under her knees. The woman has her arms wrapped loosely around his neck. The woman is kissing the man's cheek.
A man and a woman in a rooftop parking garage in San Antonio. The man is wearing a grey t-shirt and jeans, and the woman is wearing a white shirt and ripped jeans. The man and woman are holding hands and looking at each other as they run through the garage.

Kayli and Sean’s engagement session was a testament to their love—a celebration of their journey and the exciting road ahead. Set in the heart of San Antonio, their love story was beautifully framed by the charm of The Pearl. For those dreaming of capturing their love in a city, let Kayli and Sean’s engagement inspire you. Here’s to love, laughter, and a lifetime of dancing down the avenues of life together!

A special thank you to Kayli and Sean for modeling for this session. They are a real engaged couple that agreed to participate in a model call we co-hosted with Panther Eye Photography.

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We're Kylie and Daniel, a husband and wife duo specializing in wedding and portrait photography and videography. Check out our journey here on the blog, or click below to learn about us!

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