It all began in July 2022, when Ryan and Jesse matched on a dating app. After only a few messages, they decided to meet in person at Club Lucky in Bucktown, near both of their homes, for what Ryan thought would be “just one drink.” But that one drink turned into several more as the conversation flowed effortlessly - and before the night was over, they found themselves at another local bar, Lottie’s, not wanting the date to end. While Jesse was in the bathroom, Ryan texted his friend Andrea that he was on a date and already in love - describing Jesse as “very cute and smart and hardworking and very much my type. He loves to travel, is interesting, and we legit never had a break in the conversation.” Before the date was even over, Jesse had already planned their second outing, being the planner he is. They set their sights on Café Ba-Ba-Reeba, but when it was booked, they pivoted and ended up at The Royal Grocer, another local Bucktown spot. They eventually made it to Café Ba-Ba-Reeba for date number three for tapas and sangria, and date number four was to see Top Gun: Maverick for Jesse’s 28th birthday (with rosé and Cheetos popcorn, of course). About a month later, while out with some of Jesse’s coworkers at Nights and Weekends in Chicago, Jesse asked Ryan to be his boyfriend - to which he gladly said “yes.” Two months after that, Ryan was the first to say “I love you” after Jesse said something goofy, and Jesse immediately smiled and replied, “I love you too.” From there, life together only got better - more dates all around Chicago, adventures across the world, nights in with wine and Hulu, and introducing each other to friends and family as they became more deeply woven into each other’s lives. In March 2024, they took another big step and bought their first home together, quickly filling it with family, friends, and plenty of rooftop parties. Then, in January 2025, they decided it was time for the next chapter - and that they wanted to spend the rest of their lives together. Ryan and Jesse planned a trip to New York City to formally propose to each other on Valentine’s Day, celebrate their engagement all weekend, and share the wonderful news with family and friends. Now, they can’t wait to celebrate the next part of their story - their wedding - with all of you.