ASHLEY RESNICK & SHANE MASSEL

December 15, 2018 Chicago, Illinois Photographed by Collin Pierson Photography

ASHLEY RESNICK & SHANE MASSEL

Though Alex Resnick and Shane Massel weren’t a good fit, their first (and only) date still changed their lives. “While Alex and I had a great time together, there wasn’t a spark; Alex, however, thought correctly that [her sister] Ashley and I would be a great match!” Shane reveals. With Rush, one of Ashley’s favorite bands, in town for a concert, it felt like the stars aligned for the last first date the pair would ever go on. “Watching Ashley in her element jamming out on an air guitar” was a moment that stood out to Shane, and after sharing their first kiss later that night, it was clear that they had something special.

“There wasn’t a dull moment the entire wedding.”

“I realized I wanted to marry Ashley when I would miss her on Sunday nights – even though we were together – because I wouldn’t be with her all day on Monday,” Shane reflects. At a dinner the couple had with both sets of parents, he was able to privately obtain her father’s blessing. Shane initially planned to pop the question during a family trip to Cabo San Lucas for the holiday season, but unfortunately the dream ring he had picked out would not be ready in time. Though he considered using a placeholder ring, it just didn’t feel right and thus the proposal was postponed. Shortly after the new year, during a blizzard, Shane got down on one knee atop the observation deck of the John Hancock Center in Chicago in order to ask Ashley to be his wife. “I had no idea the whole thing was being filmed and that both of our families were there to surprise us!” Ashley admits of the monumental moment.