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By Daniella Gray
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A decades-old photo is going viral on social media after the woman at its center revealed that the man she would later marry was sitting quietly in the background while she was dating someone else.
Brenna Jennings (@ogbrenna) posted the snap from May 1998 on Threads. In the picture, Jennings herself is perched on the arm of a chair beside her boyfriend at the time, laughing toward another man seated by a nearby window.
Nothing could have prepared for what was to come. Her striking caption read: “I was dating the guy in the chair but I married the guy in the window.”
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The image, taken at a house party in Boston, captured what Jennings described as a moment of transition.
It was the last gathering she and her roommates hosted in her first apartment after college, with boxes packed and everyone preparing to scatter to new chapters.
The photo, snapped on film—likely by her sister—froze a fleeting moment none of them could have predicted would matter decades later.
At the time, Jennings had been seeing the boyfriend in the chair for about a month after meeting him at a live music event earlier that spring.
“We were young, tan, living in the city and enjoying each other's company,” she told Newsweek.
The man by the window, Steve De Trolio—now her husband—was one of her roommates. They worked opposite schedules, rarely spoke and didn’t socialize much.
“I thought he was quirky and did not for a minute consider him to be my ‘type,’” Jennings said. "Though I found it hilarious when he'd leave phone messages from my boyfriend as ‘the model called.’”
Her relationship with the boyfriend ended a couple of months later as life pulled them in different directions. Without mobile phones, staying in touch required landlines and early email and distance made things fade naturally.
“I don't have anything negative to say about him, we had a fun few months during an exciting time in our lives,” Jennings said.
The turning point came after the apartment lease ended. Steve left Boston to spend a month in California, asking Jennings to store his stereo while he was away.
Regular phone calls followed and something shifted. “At some point, I realized how funny, smart and even-keeled he is and found myself thinking I might actually like-like him,” Jennings said.
By the time he returned in September, the connection was clear. They officially started dating in December, and he moved in shortly after.
The online reaction to her post was bigger than Jennings could ever have expected. With over 9 million views and 238,000 likes, she had no clue that it would go as viral as it did.
Now married for nearly three decades and based in New England, Jennings and Steve have weathered life’s highs and lows together, from financial uncertainty to parenthood, fostering dozens of puppies and navigating loss.
Looking back at the photo now, Jennings has a message for that young woman in the photo: “I'd say first of all, look at how pretty you are! Stop imagining yourself to be too tall, too loud, too much. At the time, I felt like the guy in the chair was so far out of my league, and he was absolutely great looking, but I was no slouch!”
She also has no regrets about her early twenties or relationships within that decade of her life.
Jennings and Steve’s next milestone: watching their daughter graduate high school and head off to college.
“We've been a little three-pack all this time so it'll definitely be an adjustment,” Jennings said.
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