The First Date

Kyle's Perspective: Around the end of June I was hanging out with my best man, Nathan, who recommended I try Hinge, as he had some success on the app previously. I downloaded it later that night and began searching. Within that week I came across Amy’s profile. Amy actually sent the first message and began the conversation. Shortly after, we agreed to go to a bar called Rocks in Lakeview. As I was getting ready for the date, I heard the sound of thunder and heavy rain coming down. I thought little of it but hoped it would stop so I wouldn’t get soaked heading from the uber to the bar. I called my uber and then my driver cancelled. Strange I thought, but it happens. I waited and got a new driver who also cancelled. I then got a 3rd driver who sent me a message, “the streets are flooded, I can’t get to you.” He then cancelled. At this point, I debated calling off the date. I began to doubt if the date would even work out or if I was just wasting my time. But through all these thoughts was one thought stronger than the rest, “What if she’s the one?” I waited for another uber driver. This one didn’t cancel on me. She picked me up and started going back roads, avoiding the flooding got me there in no time at all. I was only 15 minutes late to the first date which is pretty good when I almost didn’t make it at all. We talked all the way until the bar closed, said goodnight and went our separate ways.

Amy's Perspective : By the time the late spring/early summer of 2023 rolled around, I was quite burned out and had taken a break from the “Dating Apps”. After the break, I decided it was time to try again, so I enlisted the help of my friend, Vanessa. She had made our mutual friend's dating profile and that friend subsequently found her future husband. Vanessa's 100% success rate (although a small sample size) was good enough for me. So I invited her over one night and over a bottle of wine we concocted the perfect profile. One of the first people I matched with following this profile was Kyle. However, after a couple of days, he still hadn’t reached out. So, I took it upon myself to send the first message (I needed to assess if I’d be wasting my time) and then Kyle will tell you that he used his best pickup line. We exchanged a "few" messages but I had no idea where this was going. A couple of days later, I was at a 4th of July party with my friends regaling them about my date the next day with “a boy I knew hardly anything about”. It’s true. Besides his height (or lack thereof, sorry Kyle) and his love of the Cubs, I hardly knew anything about him. One of my friends advised me to cancel and I was contemplating it, as I was convinced it would just be like all the other dates I'd been on. The next day, I was still feeling the same way, and I went over to Vanessa’s to catch up and watch The Bachelor. Taking her advice, I decided I’d go on the date. What was one date? If it didn’t work out, I never had to see him again. Chicago was hit with a torrential rain storm that night and Kyle was 15 min late (he still feels bad about it). Knowing quite literally nothing about Kyle, the date went quite well, as we easily chatted for hours and closed the bar down.

The Marriage Ban

Kyle's Perspective: After dating for a couple months, we had a night during December where we got together with our friends and went apartment hopping, enjoying different food and drink at each person’s apartment.

At this point in time, I knew Amy was the one for me. Every day she was constantly driving me to be a better person, and I enjoyed every minute I spent with her. I started to think about when it would possibly be a good idea to bring up the idea of marriage and had thought that it was probably best to bring up after my upcoming busy season. At least, that was the plan. However, while at the famous NYPR (where many of our friend group lived at the time), I had a conversation with one of the other guys and he gave me the best advice, “it’s never too early to have that conversation with the right person.” Inspired by this, later that night after everyone had left, I brought up my intentions of our relationship was to one day marry Amy. Well, I’ll admit, I might've rushed that one a bit. If you know Amy, she’s extremely thoughtful, and this was a sudden and very important topic that she needed more time considering. Shortly after, there was a ban on any marriage talk for the next couple of months.

It was still the best advice I had received. Thanks Marty!

Amy's Perspective: We had dated a little over 6 months when Kyle was about to enter “busy season”, an insane 3-month stretch of the year where accountants practically work all day, every day. He was more worried than I was about it, but I had friends who are accountants. I knew we weren’t going to see each other as often, but it would be short-lived. Before Kyle headed home one evening, he abruptly arose from the couch and got all serious and I had approximately 30 seconds to figure out where this conversation was going. Through the course of the Kyle’s monologue (and yes it was truly a monologue), he said that he wanted to marry me, but knew I wasn’t there/ready yet (which was true). So, I was to let him know when I was ready and he would do the rest. Thus began, what I fondly referred to as the “The Marriage Ban”. For the next few months, we would not talk about marriage at all. Admittedly, Kyle was slightly better at following the rules, but come summer 2024 the ban was lifted (thanks to Ash/Eric and Reg/Jack).

The Proposal

Kyle's Perspective: I had run through the plan in my mind every free minute I had in the past week. With the help of Eric and Ash, the groundwork was set and everything was ready. Eric and Ash, being the good friends they are, reassured me that it would all work out and wished me good luck. For weeks I had been planning to propose to Amy. I had taken the day off without Amy knowing, and Eric and Ash just so happened to invite Amy to the Shedd Aquarium that day. Little did she know that I would be there too. The planned time was to meet at the front of the Shedd around 1:30PM. Eventually, I found a spot that worked. Of course, Amy recognized the new shirt she had given me while walking up, and when she rounded the corner I think it was pretty obvious why I was there. Any nerves I had at that point were gone, and shortly after I got down on one knee and proposed.

Afterwards, we went and celebrated with some drinks. Amy was supposed to have dinner plans with some of her friends that night but I had cancelled for her. We had a couple drinks, took some pictures, then headed to a “surprise” dinner spot, Cafe Ba-Ba-Reeba. And who better to meet us there than Amy’s family, my family (Chris was there), and her friends she had dinner plans with! The food was great but the company was even better. It was great to be able to celebrate with everyone that night and really enjoy the moment.

Amy's Perspective: If it was up to Kyle, he would’ve proposed around the one year mark, but he knew I wanted to make it past a year. I went ring shopping with my mom and sister (highly recommend as it makes for a fun girls outing) and then the rest was up to Kyle. Due to work, family events, and scheduled travel I had very few weekends free in the fall. This left for limited proposal weekends, but due to unforeseen events, I honestly was a little distracted and wasn’t thinking about a ring. On one of our Sunday coffee walks along the lake, Kyle accused me of “going fishing for a ring” (honestly hadn’t thought of that, but it would’ve been nice). Flash forward to early October and my good friends Eric and Ashley (a bridesmaid) asked if I would like to go to the Shedd with them after their CPR class. I hadn’t seen them in awhile, so of course I wanted to go. They picked me up, we got lunch at Chipotle, and then things got weird. Eric wanted to “take a lap around Wrigley as he hadn’t been there in awhile” (spoiler: Eric is a Sox fan) so my spidey senses started tingling. Then we made it to the Shedd. We took a weird roundabout way around the back and Eric mysteriously lost his credit card. If you know Eric, he was not concerned enough for my liking, and I was curious as to what was going on. In the course of “looking for the credit card”, I saw Kyle (only because he was wearing a flannel I had just bought for him) and I realized I was walking into my own proposal. It was probably for the better that I had some time to prepare. Kyle did his spiel, the ring was absolutely gorgeous (thanks Maggie), and we ventured around Chicago, calling our families. The highlight of the night was celebrating with our family and friends at one of my favorite restaurants.

We are so blessed to have you all in our lives and truly appreciate the part you have played in our journey. Please pray for us as we prepare for marriage and we can’t wait to celebrate with you all come August!