We matched on Hinge and began discussing what was the most exciting TV show currently airing. This sparked easy conversation that made us want to learn more about each other. Jackson asked Cailyn on a date to the Family Dog (ironic because we both said we'd never want a pet). We both wore Vans. We both like Yorkies. We both like tattoos. We talked for nearly 4 hours and were the last people in the restaurant. Talking felt effortless and we felt comfortable together. After the date, Cailyn quickly asked for a second date before Jackson could even send the “I had a good time” text. She couldn’t let a good one like him get away!

One of our favorite ways to vacation is exploring all a new city has to offer. So we booked a trip to Philadelphia, a city neither of us had visited. The morning after we arrived, we woke up in our hotel room, and Cailyn threw on a pair of compression shorts and an oversized Jelly Roll concert t-shirt. The itinerary for the day included visiting museums and a lot of walking. Jackson, already ready for the day, said, “Are you sure you want to wear that to the fancy museum?” Cailyn responded with “You’re right,” but secretly thought it was odd that Jackson would comment on what she was wearing since he's usually so go with the flow! But she put on a dress knowing if she wanted a picture taken at the museum, it’d definitely be better in a dress than her Jelly Roll shirt. While Cailyn changed, Jackson made the hotel bed and sat on the edge waiting for her to finish. As they were about to leave, he asked, “Can I talk to you about something...?” He proceeded to ask her if she remembered how, not long after they arrived, she accidentally said “when we get ‘home’…” referring to the hotel. He told her that she "was on to something…” and described how he could be anywhere in the world, doing anything at all, and as long as Cailyn was there, it would, in fact, feel like home. Because she was his home. At this point, both of them were crying. He ended by getting down on one knee and asking Cailyn to marry him...and she said yes! We decided to keep our engagement a secret for the rest of our trip, so we could fully be in the moment and enjoy it together.