Woman found a throwback photo with her ex boyfriend from a 1998 party — then one unexpected detail in the frame left her stunned
Old photos often hold stories people do not notice at first. One such photo from a small house party in Boston in May 1998 caught attention online. The image shows a young woman, Brenna Jennings, laughing while sitting on the arm of a chair beside the man she was dating at the time. Decades later, she looked again and realized the moment held an unexpected twist. On February 26, 2026, Jennings, who goes by @ogbrenna, shared the photo on Threads, as per Newsweek.
In Jennings’ picture, another man can be seen sitting quietly near a window. That man was Steve De Trolio, the person she would later marry. Her caption summed up the surprise, “I was dating the guy in the chair, but I married the guy in the window.” The photo was taken during the final party she and her roommates hosted before leaving their first apartment after college, when everyone was preparing to move on to different stages of life.
At the party, Jennings had been dating the man in the chair for roughly a month, having met him at a live music show earlier that spring. She remembered that time as fun and carefree. “We were young, tan, living in the city and enjoying each other's company,” she commented. The photo itself was taken on film, capturing a relaxed night among friends. At the time, Jennings had no way of knowing the photo would take on a different meaning years later.
De Trolio was simply Jennings’s roommate then. They worked different schedules and rarely spent much time together in the apartment. Jennings never imagined he was the kind of person she would be interested in, and thought he seemed a bit odd. “I thought he was quirky and did not for a minute consider him to be my 'type,'” she told the outlet. Still, she remembered one small detail that made her laugh later, when he would pass along phone messages from her boyfriend and jokingly say that “the model called.”
A few months later, Jennings’ relationship with the boyfriend ended as their lives moved in different directions. Back then, without mobile phones, staying in touch was difficult, and the distance slowly drifted them apart. Around the same period, De Trolio left Boston for a month in California and asked Jennings to keep his stereo while he was away. They began talking more during that time, and like many friendships that grow through simple conversations, their connection slowly started to change.
Jennings later realized she admired De Trolio’s humor, intelligence, and calm personality. “At some point, I realized how funny, smart, and even-keeled he is,” she said. When he returned in September, their bond had become stronger. Connections like these seem to happen by chance, but later feel like the universe had a plan all along. They officially began dating in December, and he soon moved in. Today, after nearly three decades of marriage, the couple lives in New England and is preparing for another important milestone as their daughter nears high school graduation and prepares for college.
For more such content, you can follow @ogbrenna on Threads.