I always told myself that I would NEVER meet my significant other on a dating app. I hated EVERYTHING about them-- the swiping, sending messages that went unread, receiving dozens of messages that only said "hi" or "what's up," and having conversations that went nowhere. I tried the apps off-and-on for 6 years but all that resulted were dates who stood me up, dates who were late because dogs pooped on their pants, or dates who only referred to themselves in the 3rd person. By July 2019, I was over dating! I was starting to come to terms with being single forever, especially because the same profiles started popping up on the apps. I was convinced I had gone through every single eligible bachelor in Chicago. I made a rule that going forward, if someone messaged me something other than "hi" or "what's up," I HAD to respond. Well, one day someone messaged me "Who's your favorite NFL team?" and the rest is history. I have to admit, I don't remember a lot about our conversations because I (incorrectly!) assumed Matt was just like everyone else and eventually the conversation would fizzle and end. I would respond to his questions, ask my own, but wouldn't check the app for days at a time to see his response. At some point during those 2 weeks, Matt asked if I wanted to get a drink with him but it took me 4 days before I saw it. Thankfully, when I eventually responded he was still willing to meet up. On the morning of our date, I was trying to think of every excuse in the book to bail. I didn't want to experience the letdown of another awful first date. Coincidentally, my younger sister also had a first date scheduled at the same time and she said she would go on her date if I went on mine. I agreed but told her this was going to be my last first date EVER-- after that night I was going to delete the apps forever. Well, Caroline never did go on her date but I still went on mine and it turned out to be the greatest first date ever...and also my last first date.

Leigh Anne is from Connecticut and her parents still reside there. I had to figure out a plan to make a trip out there with the reason not being suspicious. Luckily the White Sox had an upcoming series at nearby Yankee Stadium. I asked Leigh Anne if she would be interested in going to watch the Sox play in NYC and we could spend the rest of the weekend at her parents’ house. It was also her dad’s boat club opening week, so Leigh Anne thought it was a great idea. Unfortunately, the Sox lost a close game, but I was able to ask her dad, Joe, the important question. Joe said yes, but he asked that I make it a surprise. We had plans to make an anniversary trip to the Michigan upper peninsula. I kept asking her if the scheduled date was going to work for her. (I was trying to get her to think the question, that didn’t happen in Hawaii, would happen there). On our second anniversary, we went to dinner at Gibson’s Italia. Gibson’s Italia has always been our go to restaurant for special occasions. Outside of the great steaks, they have possibly the best dessert in Chicago, banana gelato (yea, it’s that good). I called Gibson’s in advance to ask them to put will you marry me on the plate. It was the typical end of August night, so I had to put the ring in a baggie in my pocket since it was too warm for a jacket. I spent half of the dinner trying to work the ring out of my pocket, while not trying to be obvious. I was a bit nervous, and only ate about 1/4 of my steak (luckily Leigh Anne didn’t notice that, but she did notice I was wearing sneakers, so assumed this was not going to be the night). After dinner, they didn’t bring dessert menus. After about 10 minutes, I saw the waiter coming out with a dessert plate, but it wasn’t for us. About 5 minutes later, he came out with another one. A plate with banana gelato and the writing will you marry me. He gave me the nod, so I got down on one knee as he delivered the dish to table. Leigh Anne was startled by the surprise, but after asking if this was real, she did say yes. I think the initial yes was for the banana gelato, but she also said yes to me too.