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Our First Trip Together…

February 20, 2026

Key West 2024 – the trip that sealed the deal for both of us.

So, if you’ve been following along, then you already know that Jason and I met on a dating app back in 2024. We each rode our motorcycles for what we thought would be a short meet & greet and then possibly a short ride. We had already discovered that we were both members of the same riding group and didn’t live too far apart. We had been talking for a couple of weeks but hadn’t met in person yet. That meet-up turned into a four hour date with me on the back of his bike! We both felt it on that first date, that we were destined to be together. Fast forward a couple of weeks later and I was at Thanksgiving with his family. Then, a couple of weeks later, he invited me to take a weekend ride to the Florida Keys. That was the trip that sealed the deal for both of us!

We both knew what we wanted in a partner and both felt that we had already wasted so much time in the dating pool, so we agreed to jump in head first and speed up the process. We hadn’t spent any time apart since that first date. Initially, we discussed taking a camping trip, but decided a trip to Key West sounded more appropriate for our first trip together. That would give us an opportunity to get to know each other better while providing some entertainment as well. The trip started out pretty nice, but by the time we arrived in the Keys, the sun was setting and the temperature was dropping rapidly. We were cold and our bodies were aching due to tensing up from the cold temperatures. We were only going to be there for the weekend, so we didn’t have any time to waste. Jason had reserved two beds for us at a hotel off the main strip and a golf cart for sightseeing. Yes! He was a complete gentleman the entire weekend and he still is!

I think we both enjoyed ourselves, and each other, more than we had enjoyed anything in quite a while. Jason had reserved a golf cart but by the time we arrived it was already pretty late. We took a quick drive up and down Duval Street and then we headed back to the hotel. It was too chilly for the pool so we headed for the hot tub/jacuzzi. We think everyone else had the same idea, because it was pretty full of people. We met a married couple that were quite intoxicated and the female was pretty chummy with Jason. 🙂 They kept offering to buy us cocktails from the pool tiki bar, but we weren’t drinking at the hotel. We decided that we really couldn’t have a private conversation in the hot tub because the female really wanted to socialize with us. We were exhausted from the long, cold ride and making rounds up and down Duval Street, so we headed to sleep. Imagine our surprise at the end of the trip when we checked out and there was a bar tab! It appears that someone decided to charge their tab to Jason’s room.

The following morning, we both mentioned how loud the roosters were overnight and had kept us awake. The hotel didn’t have non-dairy creamer or milk and I’m vegan, so we took a short walk across the parking lot to the local coffee shop for some caffeine. There were roosters and chickens everywhere! We sat outside with our coffee and they stayed right under our table, waiting for scraps. Then we had breakfast back at the hotel and spent the morning talking. It was a beautiful day and the temperatures had rebound from the night before, so we took the golf cart out to explore the island.

I think we were both surprised at how comfortable we were with one another in just the few weeks since we had started talking. We both had a very familiar and natural feeling together. It was so easy to talk and share personal history, that it felt like we had known each other for a lifetime. We spent the day sightseeing, laughing, getting to know one another on a more personal level and making memories. There was something magical in the air that weekend, for certain! I like to think it was fate that brought us together. Whatever it was, it was definitely spiritual. I have my suspicions, but we’ll leave that for another time.

It was the holiday season, so I thought that must be it. That must have been the reason that I had the feelings I thought I was having already. Key West is absolutely beautiful at Christmas time. If you haven’t been to the Keys, then I highly recommend that you go during the holidays. Jason loves the holidays, specifically Christmas. No joke! When we moved in together, I learned just how much he loves the holidays! He loves Santa and has over 50 collectibles! His dad had been giving him one for Christmas for nearly his entire adulthood. And that’s also a story for another blog! So anyway, I was almost certain that his feelings weren’t validated and I contributed them to the season too. Boy was I wrong!

Jason had already suspended his dating profiles after our first date, and I had deleted mine. But by the end of our Key West trip, we were in a committed relationship and he had deleted his too. Within seven months, we were living together with both of our dogs. Yep, that’s a story for a long blog. Life has definitely thrown us some challenges, but we have successfully overcome them all so far.

We haven’t looked back and have no regrets!

Hugs for now,

Val