Jackie and Kayla

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How We Met

I had recently gotten out of a serious relationship and was ready to date around because as part of my military medical training that year I would move every four weeks to a different hospital all around the country. There was no way I was going to find love in this tumultuous time. My first stop was Tacoma, WA. My best friend had met this girl named Kayla at Gossip Grill, San Diego’s lesbian bar, a few months prior, and kept raving about how cool she was. She was going to set us up since Kayla was from Seattle and knew Washington. I thought this was for a date and loved her look.

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My best friend told Kayla that I would be up there and asked if it was okay for me to have her number, not mentioning anything about me being interested in women or wanting to date. I would get up to Tacoma in January 2017 so I started texting Kayla over Christmas break… no response. I didn’t want to look desperate so I didn’t text again. A few weeks into January when I was in Tacoma, Kayla realized that she forgot to hit send on her text message response and apologized profusely. From then on we texted nonstop, sharing songs and stories and a lot of laughing. It took her a few days of texting to realize that I thought she was super cute and that I was pursuing her. We finally met at a little dive bar, and I remember her beaming blue eyes showing through her glasses and that she was a really good hugger. I kissed her at the end of the date. For the rest of the month, we would meet halfway between Seattle and Tacoma for dinner during the week and I would spend my one day off a week with her. She then spent the next year traveling with me every four weeks to my next duty stations for the year, from Hawaii to Georgia to Maryland and now settled in San Diego.

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How They Asked

I had the ring since early April with the initial plan to propose in mid-April in Seattle with all of her family. However, COVID-19 had different plans in mind. I was deploying in June so I needed to come up with something quickly. My best friend, the one who introduced us, helped me come up with a plan.

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We would have a going away party for my deployment and surprise her there. Logistically it was difficult because Kayla and I were both home full-time due to the pandemic, and I am anything but a sneaky person. I crafted silly reasons to go over to my best friend’s house and check on the most perfect rainbow-painted signs with white wooden block lettering she was making for the event.

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The week before, I scrambled to get a gluten-free bakery to create the most beautiful cupcake setting for the ring. To give context for my not sneakiness, the bakery called me to finalize everything when I was sitting next to Kayla on the couch, I answered the phone with my Ben & Jerry’s in hand, panicked and ran out the house. Thankfully, she didn’t question too hard. I also prayed to the Internet gods that a photographer would be available for the next weekend to capture the event. When we talked about the engagement months ago her one request was to have it photographed. They had someone available!

Due to COVID-19, the easiest way for a get together was at the park so I ran and drove by the park multiple times a day in different lighting to see the perfect spot. On top of that, we were closing on a house together and the moving day was the day prior to the party. So many things could’ve gone wrong. But, the moving day went great, and I woke up the next morning feeling very nervous.

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All Kayla noticed was that I was being more quiet than usual. She also always complains of dry hands, and I thought she would be upset if the pictures showed that so I strangely kept reminding her to put lotion on her hands the day before and all day leading up to the engagement. We picked up the cupcakes on the way to the party and I placed the ring in the cupcake in the store.

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When we got in the car she asked if the cupcakes looked good so I lifted the lid on another box of desserts we bought. Again, no more questions. We pulled up to the park and 15 or so of our San Diego friends were gathered at a picnic table full of drinks and food. Everyone knew what was about to happen. Our friends distracted Kayla as we struggled with Video chat to have her family and friends present. Once they were online my best friend got everyone’s attention and said “Jackie and Kayla, since Jackie is leaving we got you guys a gift if you will just follow us.”

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Everyone went to where the signs were face down in the grass and they told us to stand in front. Kayla started to notice everyone else form a circle around us. One of my friends each took one of the signs and once they were in place I turned to my love and said “Kayla…” at this point she gasped and started to cry. “This year has been a whirlwind.

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We finally got to live together in the best city in the world as we started an internship, added another dog to our family, and bought a house. You know how indecisive I am – from not knowing where to eat to where the best place for the mustard is in the fridge. One choice that has never been hard is to love you with all that I have. Kay, I want to choose you for the rest of my life. So I brought all of our family friends here to help me ask you a question.”

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At this point, my friends revealed their signs one at a time. I told her to open the cake box that I had made her hold, I got down on one knee and asked her to marry me. She said yes! We celebrated, I held the large cake box for too long, and we made it really special with her family on zoom. Two weeks later I left for deployment which is where I’m writing this from now. I cannot wait to marry her.

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Special Thanks

Jade Seabrook
 | Planning