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Brenna & Tyler

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Brenna Futty

and

Tyler Cullum

October 25, 2025

Galena, MD
123 days123 d5 hours5 h44 minutes44 min49 seconds49 s

How We Met

We were introduced to each other by mutual friends in 2015. We started talking, texting, and snapchatting 24/7. One day in the cafeteria, a mutual friend went up to Tyler and asked if we were dating, and he said "Yeah, I guess so!". So romantic! If you would have told our 14 and 15-year-old selves that we are getting married after 10 years of dating, have two cats, and fall in love more and more every single day, we'd probably believe you!

The Proposal - Tyler’s Version

Of course, I knew I wanted to marry Brenna at an early point in our relationship. The real question was; what is a broke high school, then college kid to do? Well, the moment I started working after graduating college I started saving. Two days after our eighth anniversary (October 28th at 2am, scrolling through rings), I bought it! I immediately called our friend Eleanor, who promised me she had not been drinking (why else would she be up this late?) and told her about it, and how I wanted to propose while we were in Chicago in December. The next few weeks consisted of finding the right place to do it, and booking a celebratory dinner for afterwards. While on the phone with Eleanor talking about this, she said something along the lines that I had mentioned this months ago. I then called her out that she had been drinking that night and lied to me! XD Keeping my plans under wraps was the hardest part. I had to get her family’s blessing and show both our families the ring without her knowing. I had to tell our friends we were going to Chicago with (thank you for being our photographer Mei). Worst of all I had to hide the ring (and the unproportionally large box it came in) somewhere in our tiny Towson apartment that she couldn’t find. Thankfully, Chris Lane literally has a song about it and I just hid it under my side of the bathroom sink! (how did I get away with that?!) Fast forward to Chicago. We landed Thursday night and Friday was a jam-packed day (thankfully to not allow much time for overthinking). The plan was; go to the Christmas market at Wrigley Field in the morning, explore Lincoln Park (propose while there), then to the Chicago Zoo for Christmas lights, then dinner. Everything was going swimmingly, then we got to Lincoln Park. My plan had been to just feel out the vibes, act like we were getting pictures in a bunch of locations, and enjoy the park. We stopped for Brenna to go to the bathroom and everyone saw I was stressing. They hyped me up and we then found the perfect, quiet spot on a little pier on the South Pond. I had a sticky note with what I wanted to say but wouldn’t that look weird? Instincts took over, I blacked out, and the next thing I knew, I was fumbling for the ring in my pocket on one knee and asking her to marry me. She said yes! We cried, enjoyed the rest of the best day of our lives, and toasted to our future at dinner that night.

The Proposal - Brenna's Version

Tyler and I had planned a trip to see our best college friends in Chicago, this was in December of 2023. I remember getting my nails done right before the trip with my mom-mom thinking "hmm...this is oddly suspicious". I asked her if she knew anything about Tyler possibly proposing, she replied "Brenna, don't get your hopes up". I was crushed, I knew if she said that, then it probably wasn't happening. Little did I know, this was a part of the whole plan all along. We flew into Chicago with Erik and Mei and met Eleanor and Trevor when we landed. The first day went by with lots of sight seeing, but no ring. The next day we all dressed up to go out for the day, everyone was acting weird, Erik especially. We went to a cute pop-up Christmas Village in Wrigley Field. We then arrived to Lincoln Park, where we walked around for a while. We would arrive to a ideal picture spot, get pictures, and move on to the next spot. Eleanor and Mei told me to take off my jacket and put on my heels that I packed for some unknown reason of course, and we kept walking...weird. We arrived at this beautiful pond in Lincoln Park, the sunset was gorgeous. Then, Tyler hugged me and was shaking like a leaf, I asked what was wrong, and he got down on one knee and proposed. It was one of the best days of my life so far and to be surrounded by our best friends was so special. We all went to the Chicago Zoo after and then had an amazing dinner in a cute little Italian restaurant. We all shared a champagne toast and now here we are, 10 years later from when we first met, and I get to marry my best friend.

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For all the days along the way
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