Caryn & Jeff matched on Bumble on July 5, 2021. Caryn had been very active on the apps after making dating a priority, while Jeff was relatively new to the dating scene. So new in fact that he didn't realize that messaging for weeks on end without asking Caryn on a date would put him in the "pen pal" category. Caryn was almost ready to write him off, but Jeff insisted that he was the real deal and quickly scheduled a live date for July 29 at Bub City. Upon meeting, Caryn & Jeff spent over 6 hours talking and getting to know one another, with the night going so well that they shut down Bub City and later shut down the late-night Red Head Piano Bar…the first two of many bar shut-downs in their dating life. The following weekend, Jeff was flying back to Chicago for a concert. Date #1 ended with Jeff determined to find Caryn a ticket to join him (which was not easy given his exclusive pit ticket). Caryn wondered if Jeff would follow through on securing date #2 and grew doubtful when he still hadn’t found a concert ticket for her upon landing in Chicago Thursday night. When Jeff disappeared from his usual texting for a long while, Caryn was convinced he was out on another date. Little did she know, Jeff was running around town trying to get her a ticket. Once Jeff texted they were on for the concert, Caryn realized that Jeff is a man who keeps his word and that he was "special & different" (which she still tells him to this day). On date #2 at an outdoor concert, a giant storm began to approach and the venue announced that everyone must leave as major wind gusts began to blow the speakers and the stage. Being prepared, Jeff pulled out ponchos he had brought along just in case. Caryn struggled to get her poncho hood on, and Jeff assisted. The two locked eyes and Jeff and was instantly consumed by Caryn (this was the moment he would later refer to as the time when something “clicked” for him). The next week, Caryn had plans to visit her friend in Colorado, not far from where Jeff was working that week. They decided they would meet for a "date night", which quickly turned into a “date week”, and ended with Caryn & Jeff escaping to Estes Park for a long weekend. At the end of the trip, Caryn & Jeff decided to make one another a priority and seriously date despite the long-distance challenges. Through weekends together, they quickly discovered that despite having little in common on paper, Jeff being a farm kid from Southern Indiana, and Caryn a Jewish girl from Chicago’s suburbs, they connected fast and hard in a way they never had before with anyone else. When they initially met, they were both getting ready to throw in the towel with dating and move on to their respective personal “Plan B”s in life. But one app swipe changed that forever. Jeff then invited Caryn to travel to London for his marathon. The trip was a success and Jeff ran his best marathon to date with a time of 3:18, which Caryn predicted to the minute 10 days before. After that trip, "the rest was history". Later confessions would reveal that love was in the air very early on. While Caryn decided she wasn’t going to say “I love you” first, Jeff insists he wanted to say it on marathon day in London, October 3. He finally got around to actually saying it on November 22. Immediately following that moment, Caryn & Jeff decided they didn’t want to live without one another, and quickly started talking about a wedding. Jeff schemed up a special plan to ask Caryn to marry him, which he did on February 5. Jeff popped the question at Elske's outdoor fireplace, followed by a surprise celebration with both their families. It took a while for Jeff and Caryn to adjust to becoming all the clichés that they never quite believed were true, such as “when you know, you know”, “all it takes is one”, and "you'll find love where you least expect it". Apparently, all along, Caryn should have been looking on FarmersOnly and Jeff should have been searching on jdate!