From High School Sweethearts to Forever: Abby & Jordan’s Vintage-Inspired Engagement Session

Some love stories come full circle in the sweetest way, and Abby and Jordan’s story is one of those! From high school hallways to a candlelit alley proposal and a vintage-inspired engagement session, every part of their journey feels beautifully meant to be. Abby and Jordan first met in 2016 at their small hometown high school. He was a senior on the basketball team and she was a junior cheerleader. In a school where everyone knew everyone, they had certainly seen each other around, but once they officially met, sparks flew! They dated for over a year before life took them in different directions for college.
 

Like many young couples, distance led them to part ways. But six years later, in 2023, they both found themselves back in their small hometown. With a little encouragement from Abby’s mom (who always adored Jordan!), the two reconnected and the rest is history! Now, after over two years back together, they’re planning to say “I do” this November.

On November 8, 2025, Jordan proposed in downtown New Albany, Indiana. Abby thought it was just a normal night out with close friends — dinner and drinks at a new bar. As the evening wrapped up, their friends spotted a charming alley across the street strung with lights and suggested taking a few photos. After snapping a few pictures of their friends, Abby and Jordan stepped in for their turn. What Abby didn’t know was that their friends were secretly recording! "Unfortunately (it’s funny now), Jordan was getting nervous and choked up, so he never actually said anything," Abby shares. "He didn’t ask 'Will you marry me?' He just pulled out the ring and made a noise like 'Eh?' It was so funny and cute, I obviously said yes, and then we had to go to my parents house to show them. Again, little did I know, he had a huge surprise engagement party there with all our friends and family. It was the best night ever!"
 

Jordan chose the ring entirely on his own, and he absolutely nailed it! All he had to go on was a small Pinterest board and one request: an emerald-cut diamond. He secretly borrowed one of Abby’s rings to get her size and went to the jeweler solo. The result? A stunning one-carat emerald diamond with small diamonds lining the band and a gold back detail. 

Abby knew long before she got engaged who she wanted to photograph her wedding. She had been following Gabriella’s work for some time and instantly fell in love with her candid, warm-toned, classy style. "So, as soon as I had any sort of thought that Jordan might propose, I reached out to her on her availability," Abby says. "I literally planned my wedding to make sure we could book her!"
 

Originally, Abby and Jordan had planned to shoot their engagement session in a historic old library. But just before their session date, the building closed for renovations, forcing a last-minute location change. We think it couldn’t have worked out more perfectly! They moved their session to a beautiful vintage home that now operates as a bed and breakfast. The space was filled with old-world charm — ornate details, romantic light and timeless character. They took photos in one of the bedrooms, cozying up on the bed, and even captured dreamy shots in a classic clawfoot tub!

Abby turned to Pinterest (of course!) and past galleries from Gabriella for outfit inspiration. She found a gorgeous satin dress with a vintage feel and paired it with elegant heels. Jordan kept things simple and timeless in a white button-up and black dress pants. Their look was effortless, classic and perfectly aligned with the romantic, historic feel of the location.

Even before getting engaged, Abby had a vision for their wedding, especially when it came to color. Her Pinterest board was already overflowing with inspiration. Now, with their November wedding planned at The Jefferson, their formal theme is coming together beautifully! "The Jefferson venue is very black and white, so we are going for a more formal theme," Abby describes. "My colors are merlot and moss so the colors are very much dark pink and green. I’m hoping for a lot of florals, black ribbons, white tables, etc. I’m still figuring out all the little details but I think our theme is going to be so pretty and timeless!"

Even more special? So many loved ones are playing meaningful roles in their day. Jordan’s aunt will officiate. Abby’s aunt will sing. A family friend is handling the flowers. And Abby will be wearing her mother’s wedding dress. Their celebration won’t just be beautiful, it will be deeply personal!

 

 

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