Our Favorite Chicago Love Stories

Five couples share the sweet stories that led them to "I do".
by Rachel Sylvester
  1. L'Oreal & Jeff

    classic downtown chicago engagement
    Kathleen Hertel Photography


    After a New Year's promise to L'Oreal that 2013 would be “the best year of her life," Jeff planned a surprise proposal by enlisting the help of her family and friends. While L'Oreal was getting ready for a lunch date with her sister and mom, Jeff took advantage of the distraction by popping the question right there in her kitchen. But rather than respond with a resounding "yes," L'Oreal assumed the proposal was a joke and simply walked away. “Seriously—she left me alone on one knee in the kitchen!" Jeff says. The seriousness of the proposal eventually sunk in when the couple pulled up to a restaurant filled with family and friends ready to celebrate their engagement. “He even reached out to my dream wedding photographer to capture the party," L'Oreal says. “It was the best surprise ever." The ring: Haring Jewelers

  2. Melissa & Bradley

    wicker park engagement photo
    Two Birds Photography


    After four years of dating, Bradley proposed to Melissa on Valentine's Day—not because he's a fan of the holiday, but simply because he was getting impatient. “By that point, I had the ring for more than a month and just couldn't wait any longer!" he says of the vintage ring he had picked out. Since Melissa is an artist, Bradley bought her a large art history book as a gift and cut a hole in it before placing the ring inside and wrapping it. The only problem? Melissa flipped through only half of the book without getting to the actual ring. “I awkwardly told her she should skip to the end since it's really interesting," Bradley says. “She finally found it and said 'yes'—I was so relieved!" The ring: Etsy.com

  3. Julie & Marcus

    chicago trump tower engagement
    Kelly Braman Photography


    After first meeting years ago through mutual friends in college, Julie and Marcus planned a spring trip to Lake Geneva for a romantic weekend away. Despite the bad weather, the couple stumbled upon a small Italian restaurant where they enjoyed dinner before Marcus excused himself to go to the bathroom. It was then that Julie texted her best friend two disappointing words: not happening. Little did Julie know that a proposal was coming just moments later. "Marcus came back to the table, took my hands and asked me to spend forever with him," Julie says. “I was shaking and couldn't believe he was actually asking me." The ring: MVT Gems

  4. Becca & Zach

    modern chicago engagement
    Britta Marie Photography


    After first crossing paths in a Dallas bar during a football game, Becca and Zach exchanged numbers only after Zach spent the afternoon working up enough courage to approach her. “The rest, as they say, is history!" Becca says. To celebrate Becca's birthday, they embarked on an 11-day European vacation, which included stops in England, Spain and Italy. While the couple explored the sights in Rome, Becca noticed how fast Zach was speeding through their walking tour. “I was a little put off by his pace," she says. The reason for all of the rushing? Zach had big plans to propose at the top of the Spanish Steps. “He convinced me to hike to the top, where he popped the question," Becca says. “It was the perfect ending to a great trip!" The ring: Ethan Lord Jewelers

  5. Karen & Ken

    hip downtown chicago engagement
    Kate Botwinski Photography


    Despite dating for 13 years, Ken managed to take his high school sweetheart by complete surprise when he popped the question during a romantic anniversary dinner. “He's not really a romantic sort of guy, so I wasn't expecting it," Karen recalls. “He bought flowers for me when we first started dating, so I always joke that he doesn't buy them for me anymore!" After being led to a spot by the stage, Karen saw red roses waiting on their table. “A musician played love songs throughout dinner and after the meal, Ken asked me to 'please be his lovely wife,' " Karen says. “Out of all that he said, that's the only phrase that I remember!" The ring: Hearts on Fire

Up Next