5 Sweet Proposal Stories from Chicago Couples

Windy City-based couples share the romantic stories that led to "I do."
by Rachel Sylvester
  1. Tiffany & Joshua

    lake michigan engagement shoot
    photo by Ed & Aileen Photography


    Four years after they first met, Tiffany and Joshua traveled to Colorado with their son, Lincoln, to visit family. On a date night in Denver, Joshua took a surprise detour to the couple's favorite lookout spot on a nearby mountain. “Once we got there, he pulled out a speaker and I started to dance," Tiffany says. When she eventually turned around, Joshua grabbed her by the hand and quickly took a knee. “Every time we go up there, we have a pinecone fight, so my first thought was that he had found one and was trying to throw it at me," Tiffany says. “But nope—he was just asking me to marry him." The ring: Diamonds by Shelly

  2. Lisa & Tim

    chicago engagement shoot
    photo by T&S Photography


    Despite becoming close friends and, later, coworkers, it took three separate attempts for Tim to convince Lisa to go out on a date. “I finally agreed and it was the best decision I ever made," she says. Three years later, the pair traveled to Traverse City, Michigan, to celebrate Lisa's birthday. Once there, Tim took the chance to propose as the two sat on a dock overlooking Spider Lake. “The sun was setting when he got down on one knee," Lisa says. “This time, I made sure he didn't have to ask more than once." The ring: Ethan Lord Jewelers

  3. Neeral & Anu

    chicago same-sex engagement shoot
    photo by Matushek Photography


    Nearly nine years after they began dating, Anu (right) enlisted the help of their cat, Milo, to propose to Neeral on his 30th birthday. After reading Anu's heartfelt card, Neeral turned to find him on one knee, holding Milo, who wore the engagement ring on his collar. But before Neeral could process the proposal, Milo made his escape, taking the white gold ring with him. “We spent several minutes coaxing our cat out from under our bed before Neeral was finally able to say 'yes,'" Anu says. The rings: Anu: Tacori; Neeral: Rony Tennenbaum

  4. Kelly & Troy

    millennium park engagement shoot
    photo by Kristin La Voie Photography


    After meeting three years ago in Austin, Texas, Troy popped the question while the two visited family in southern California. “Troy let me know we had dinner reservations at 6 p.m., and all I could think was, 'How old are we—80?'" Kelly recalls. Before the meal, the two shared a few glasses of champagne in their hotel room and then took in the resort's scenic ocean views from a nearby cliff. That's when Troy took her by the hands. “I immediately knew what was happening and started bawling," Kelly says. “I couldn't have been happier." The ring: Nick Ohanessian

  5. Bridget & Dan

    Chicago theater engagement shoot
    photo by Megan Saul Photography


    Dan had planned an intricate proposal with the help of Bridget's family, but Bridget's father was hospitalized just days before he was going to pop the question. “He passed away four days later, but it was a blessing to know Dan had asked my dad first," Bridget says. Later that same year, Dan caught Bridget off-guard with a proposal while the pair did laundry. “We told our cats, who seemed pretty indifferent, before going across the hall to celebrate with friends," Bridget says. “It was perfect." The ring: Wedding Bands & Co.

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