KATLYN & TRENT | Olin Park Engagement in Madison Wisconsin

Summery Olin Park Engagement in Madison Wisconsin

We had BEAUTIFUL weather at Katlyn and Trent’s engagement session at Olin Park in Madison, Wisconsin! The hot weather the day before cooled off, and it was just beautiful! We met them at Olin Park, which has one of the most beautiful views of Madison. Along with a wide variety of locations for a session!

Katlyn and Trent wanted a nature-filled session with lake views of Madison. Their wedding will be very urban, so they wanted their engagement session to be a 180 from that! I think we entirely fulfilled this! Along with never-ending laughs during the session!

Let’s get to know these two rad humans!

How did they meet?

Katlyn’s version:

I was newly (ish) single and hated the online dating world. I had scheduled a second date with a Chicago firefighter. That I was jazzed about until he completely stood me up. Not one to let getting ready and dressed up go to waste, I called my best friend for backup. And we promptly went to a movie and shopping – in which we managed to get slightly intoxicated (I always remember this as the dressing room montage scene in The Sweetest Thing if you’d ever seen it).

We decided ‘just one more’ at Joe’s on Weed. At which point, sitting at the bar, a very intoxicated man proceeded to direct his full lopsided gaze at my friend. Who being the sassy Chicagoan she is, did not respond well to this. Enter a knight in shining armor, Trent. He not only placated the situation but invited me to stay with him and his friends to watch the live band. Who was I to say no? I’ll spare the rest of the evening details (nothing good happens after midnight, right?), but needless to say, for some reason, he continued to contact me in Chicago, Milwaukee, and even Greece – and the rest is history. 

Trent’s version: 

My friend Luke from Central WI had come to Chicago to visit. As I had only been living there for a short time. And we had plans to go to Milwaukee to a Bucks playoff game that Sunday.  Luke, not being one to shy away from an opportunity to let loose. Had decided it was a good idea to rip a few shots of vodka before us going to Joe’s on Weed. To meet another mutual friend to see a band as we were waiting for our friend Al to show up at the bar. Luke, being slightly intoxicated kept staring at Katlyn’s friend Mar (who had been somewhat overserved at that point as well.)  Mar, not being one to not voice her opinion, decided she didn’t like Luke staring at her, and Luke chirped back with some words of his own. 

In most instances, being the voice of reason. I had to temper both parties down, which involved a conversation with Katlyn.  Once Katlyn had sent Mar home in an Uber before the band started. Something about her drew me in, and I wanted to invite her to stay and watch the bar with us.  She took me up on that offer.  After spending most of the evening talking to her vs. Watching the band, a spark there wanted me to keep talking to her.  I went to Greece the following week for work. And even during that time, I wanted to text her and talk to her. Because I realized quickly she was a person I wanted to get to know and be a part of my life.

How did you know your partner was the one?

Katlyn:

After getting through a pandemic together and buying a house. The next natural step in everyone’s heads was that we’d get married. But knowing Trent, I knew his mind could only focus on one big life event at a time. And homeownership is a whole other test of one’s relationship. So as many people said, ‘oh, it has to happen soon,’ I truly set my expectations at maybe June or the end of 2022. So when he jumped at the opportunity to book our birthday trip to my aunt’s condo in Florida. I thought nothing of it. We had gone out the night before my birthday, and a massive fireball shot somewhat doomed me the next day to want to do any planned activity.

I would have been thrilled to watch Disney movies and order sushi in bed. But Trent was very persistent about what we were doing that day, knowing that I usually liked to have a plan. But of course, I didn’t and made things rather difficult for him. What we DID plan, though, was a fabulous 7-course dinner at a new restaurant. So right before dinner, dragging myself out of an afternoon nap to the balcony. To watch a very overcast but beautifully blue sunset. I had a ‘me’ moment with Trent behind me, thinking how much I love turning 34. Trent agreed and said, ‘it’s going to be the best year yet. And then everything after that is a blur because I legitimately blacked out when I realized what he was doing, so don’t ask me what he said – I remember my answer being ‘are you f&#*ing serious?!’ instead of ‘yes.’ And I wouldn’t have had that moment any other way 😊 

Trent: 

After we became serious about buying a house around Madison, I started looking for a ring.  Ironically I had a friend, my co-best man. Who had worked in a jewelry store in a mall in Minneapolis after college.  Brad had a co-worker Jake who we would hang out quite a bit.  Jake stayed in the jewelry industry, and we ran into him in late July in Milwaukee for a Bucks playoff game.  I reached out to Jake, a manager of the Kessler’s diamonds in Greendale, WI.  Jake put me in touch with a co-worker of his in Madison, and I started the process of ring shopping.  Like most things, I do my research, and after months of looking, I found the perfect ring. 

I also had to get some help and ideas from Katlyn about what she liked. As I didn’t want to screw this up.  Going into the process, we had booked a trip to her aunt’s condo in Florida. And I knew I wanted to propose on her birthday.  Of course, the weather was great for my birthday and the days leading up to Katlyn’s birthday.  I didn’t have a plan which I know is terrible as sometimes spontaneous situations present themselves. 

I couldn’t get her to commit to any plan that day which was frustrating as usual. She always wanted to know what we were doing.  The weather sucked that day, so we couldn’t to a walk on the beach.  I carried the ring on me all day, and thankfully she never felt my coat pocket. 

Thankfully we did have a nice dinner planned that evening.  After getting ready, which ironically she was prepared before I was that night. She was on the balcony just enjoying what there was of a sunset, and I knew that was my moment.  So I took advantage of that and part of our conversation to say this is going to be our best year yet. Went down on one knee and proposed.  after which, we went and enjoyed a fantastic dinner and the first moments of being engaged!