Five Sweet Proposals from Chicago Couples

Adorable proposal stories that led these Windy City couples to say "I do."
by Rachel Sylvester
  1. Radha & Raffi

    autumn chicago engagement photography
    Husar Photography


    Husar Photography

    A Saturday visit to the Museum of Science & Industry led to a surprise proposal Radha didn't see coming. As Radha and Raffi walked through the nearby Osaka Gardens, Raffi suggested they take a picture on his new camera that syncs up to his cell phone. “I had the phone in my hands and was struggling to figure out the app when I realized Raffi had said my name,” she says. That's when Radha looked over—and down—to find Raffi on one knee. “The first thing out of my mouth was, 'The box is upside-down!' and we both burst out laughing,” she says. The ring: Tiffany & Co.

  2. Michelle & Dan

    home Chicago engagement photography
    T&S Hughes Photography


    T & S Hughes Photography

    While vacationing in Croatia, Michelle and Dan arrived on the island of Korcula after two days of exploring the mainland. Once there, the two spent the morning relaxing on a secluded beach before walking down to a rockier area to take in the sunset. As they were discussing their trip, Dan suddenly got down on one knee, scraping it in the process. “He slipped a ring onto my finger and kept repeating, 'This isn't the ring!' since he didn't want to travel with the actual diamond,” Michelle says. That's why Dan proposed for a second time as soon as they returned home from their trip. “We dropped our bags off in the hallway and Dan ran off to grab the real ring,” she says. “I could barely get out a 'yes' between all of the laughing and tears.” The ring: A Burdakin

  3. Ashley & Ryan

    chicago boat engagement photography
    Neri Photo



    Nine years after they first met at Southern Illinois University Carbondale, Ashley was surprised to come home and find Ryan watching a rom-com on the couch. “He started talking about our relationship and asked if I wanted to revisit the scrapbook I made for him back in 2007,” she says. But after flipping through the book, Ashley noticed a handwritten proposal and engagement ring taped to the back page. “To be honest, I was in such a state of shock that I have no idea what he said,” Ashley says. “The next thing I knew, the ring was on my finger and we were on our way to announce the news to our families.” The ring: Wyatt Austin Jewelers

  4. Marcia & Toussaint

    chicago engagement photography
    Brittany Bekas


    Brittany Bekas Photography

    During their third year of medical school, Marcia, Toussaint and other students started playing regular squash games against one another. But what started out as a competitive friendship eventually developed into a relationship—and later, a proposal. During an afternoon game at the San Diego Squash Club, Toussaint went to change his goggles when an attendant approached Marcia and politely explained they needed to change courts. “I walked toward the far court when I noticed Toussaint standing in the middle of the room with an array of pink and purple balloon and a big grin on his face,” she says. After first handing Marcia a love note hidden in a squash ball, Toussaint presented her with a prescription pill bottle—a nod to their careers in medicine. “I struggled with the childproof top but eventually opened it to find the most perfect ring I've ever seen,” Marcia says. The ring:

  5. Besma & Syed

    Chicago skyline engagement photography
    Christian Wilson Photography


    Christian Wilson Photography

    Five years after meeting in college, Besma and Syed bought tickets to a Jason Derulo concert, where they spent the night dancing with friends. But as a slow song began to play, Besma was surprised to hear her friends yell, “Syed, do it now!” over the lyrics. “I looked over at him and he just shrugged like he had no idea what was going on,” she says. Soon after, Derulo started to perform “Marry Me” and Syed discreetly grabbed the ring from a friend. “People in the crowd turned toward us while I just stood there in disbelief,” Besma says. “All I could hear were random girls yelling, 'Look! He's proposing!' ” The ring: Gabriel & Co.

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