Chelsea and Andrew

Marriage Proposal Ideas in Keeneland Race Track in Lexington Kentucky

How We Met

Andrew and I met at Washington College on the Eastern Shore of Maryland. I was from New York still settling into the idea of a college surrounded by fields and farms and Andrew, born and raised in Maryland, was in his Sophomore year enjoying all of the fun
college had to offer. Having just recently joined a sorority, we were having a mixer with the soccer team one Friday night when I ran into a very outspoken red-headed kid. I don’t really know if I believe in fate but Andrew was never a soccer player, so it was definitely lucky that he was there that night! I wouldn’t say it was love at first sight as the week before I was out and accidentally moved in line with someone swinging their arms with a full wine bottle resulting in two black eyes (it looked way worse than it was). This, of course, meant that the first time I met my now fiancé I had two black eyes! The one thing I really remember from that first encounter is him saying he” though my makeup was running” when I said I usually don’t look like this. I still can’t decide if that was true or him just trying to be polite due to the fact I had an absurd amount of cover-up on. We exchanged our casual hellos and I mustered up the courage to add him on Facebook (embarrassing I know) and the rest is history!

Chelsea's Proposal in Keeneland Race Track in Lexington Kentucky

How He Asked

My mom’s family is from Kentucky and while in college we started taking family trips to Keeneland Race Track for the fall meet. Andrew, being my new boyfriend, was of course invited. Since our first trip in 2012, Keeneland and Kentucky have always been “our special place”. Even when my family couldn’t attend one year Andrew and I planned the trip ourselves and took his mom! It is an easy weekend trip and we always tie in one of the Kentucky Distillery Tours the day before the track. I would recommend to anyone looking for a new easy and cost-efficient getaway!

Fast forward to Spring of this year. Andrew thought it would be fun to take some of our friends down to see why we loved Keeneland so much. I, of course, was on board and began planning immediately. When you first walk into Keenland the first thing you see is the gift shop which is more of a luxury brand store. Being a girl, this is usually the first place I hit. Andrew is not a big shopper, so he usually lets me do my thing and doesn’t ask questions. We started a tradition of having our picture taken in front of the jockey statues on the paddock which is something most people who frequent the track do. I figured I would pop in the store and then head there since it is our usual meeting place. I got sidetracked by all the potential things I could buy but definitely did not need and realized I had missed five phone calls from Andrew! I rallied the troops and headed for the statues to take our pictures before the crowds got larger. It was The Makers 46 Mile race day, so we knew it would get crowded fast! I asked Andrew to take a picture of me and the girls and he said we should take the first picture. I handed off my phone and walked over to the statues. Andrew put his arm around my back and I could feel that he was shaking. He whispered in my ear what didn’t quite seem like words at the time and all I could make out was “I’m really nervous”.

Proposal Ideas Keeneland Race Track in Lexington Kentucky

He then proceeded to tell me he had something planned to say but couldn’t get the words out. At that moment I looked out and realized that not one but all 10 of our friends had their phones out! It was then that I realized what was going on and Andrew got down on one knee. I am a very unfortunate looking crier, so I immediately covered my face. I’m pretty sure you can even hear me saying “no” initially in the video because I got so nervous!

Just when I thought the day couldn’t get any better my mom appeared in the crowd and had been in on the surprise all along! Luckily mom knew how ugly I am when I cry and brought a slew of makeup and tissues (I will be eternally grateful for that). The ring Andrew gave me turned out to be my grandmothers that he got from my mom a month before when she came to visit us in MD. Having my grandmothers ring is special enough but he even had her initials and mine engraved on the inside! It was perfect.

Andrew is a very private person and I was not expecting any sort of public display when it came time for him to propose. I was expecting more of a Friday sitting on the couch and a casual “ Hey Chels, it’s been 7 years, would you like to get married?” (I would still have said yes if this was the scenario) but this was an amazing and special moment I will never forget! With the races starting everyone dispersed to get Juleps, place their bets, and celebrate this amazing day! About an hour later I got a text from Andrew saying “You Never Said Yes!” I simply texted back “Yes!”.

Our Video

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Special Thanks

Meritage Jewelers
Ring cleaning and engraving