Robby and Diana swiped right on Tinder in May 2016, and their “for-real-just-until-August” fling began. They spent the summer pretending not to fall in love. They laughed between pitches at Wrigley, drank too much at the Cell, and never wore enough sunscreen at Montrose Beach. They talked about their shared love for family, Chicago sports, and good grammar as they walked hand-in-hand along the Chicago River, through Montrose Harbor, and across Grant Park. They dressed up for romantic date nights, rolled out of bed for Sunday afternoon brunches, and kissed under the fireworks at Navy Pier.

They made their “goodbye forever” speeches the night before Diana left for her senior year at Ithaca College in New York. On August 26, they admitted defeat on a phone call and officially became boyfriend and girlfriend. A week later, Robby took an overnight train to New York. Diana said I love you first… and Robby said it back two seconds later. Long distance sucked, but they made it work.

Diana graduated and moved back to Chicago in May 2017. Since then, Robby and Diana have celebrated every moment together, big or small. They moved in together in June 2018 and bought their first home in December 2021. Diana graduated law school, passed the bar exam, and started her first job as an attorney. Robby was promoted numerous times, won his first business pitch, and writes for clients like the NFL and the Green Bay Packers. They dance to “Congratulations” by Post Malone to celebrate every accomplishment and sing “Happy Birthday” at midnight on every birthday.

Obviously, Robby and Diana’s biggest accomplishment to date has been building their army of orange cats. They adopted Chu (the gentleman) in January 2017, Cheese (the screaming runt) in July 2018, and Chai (the fat one) in October 2023. Their furry family is now complete (because Robby won’t let Diana adopt anymore cats).

To gain acceptance into Robby’s family, Diana learned all the words to “Back Home Again In Indiana.” And to maintain his acceptance in Diana’s family, Robby pretends it’s normal to drink Malort at family events. Both families have been incredibly supportive of their relationship from the start. Diana was included in the Howard family photo in 2021 (pre-engagement!), and her mom has referred to Robby as her son-in-law for years.

Robby and Diana returned to Navy Pier for their six-year anniversary. Wearing a suit jacket and holding a rose, Robby began his proposal speech at the top of the ferris wheel. It was the perfect, private moment Diana had always wanted. As Robby neared the end of his speech, with the sun setting perfectly behind them, he dropped to one knee – almost! Before his knee hit the floor, Diana pushed him back into his seat. They weren’t at the top anymore, so everyone could see them! They laughed through tears as they (very slowly) made their way back to the top. When Robby asked, Diana said yes.