4 Dates in Lexington, Kentucky

My date in Lexington was amazing, to say the least. because I actually had 4 dates set up. I had one set up before I got to Kentucky, and I set up the other 3 all on Friday. As usual, I went into this trip with no expectations, so I was excited but also skeptical on if all the dates would show up. Well, this is how it went…


Date #1 – Kyle

After doing a bourbon tasting I received a message from Kyle. He was 33 years old good looking guy with a cute face and a great body. I was hungry and we immediately made plans to meet. Well, technically I invited myself to join him for tacos.

As I sat down I was pleasantly surprised as he smiled up at me and said hi. We immediately started to get to know each other. He was a landscaper that enjoyed going to gay bars because all his friends are married. He was an interesting mix he had some feminine interest but manly when it came to his profession. Trust me I asked if he was interested in men at all, but he’s never been interested. I went on to talk about my blog and my job as a software developer. He thought he was dumb compared to me after I told him about my job. We continued having playful conversation getting to know each other. Apparently the girls he’s been on dates with lie about their weight, so he was pleasantly surprised I was how I looked in my pictures. He knew he was hot or as he said ‘pretty’ but was not cocky at all as he owned up to his insecurities. He’s a super sweet guy and would definitely look forward to seeing him again if he comes to Atlanta


Date #2 – Mike

Mike was my second date in Lexington. I met up with him right after eating tacos with Kyle. He told me to meet him at a bar called Double Dogs. Mike seemed excited to see me when I got out of my Lyft. I walked inside the bar and sat next to him at the bar. He was cute and came off a little quirky.

He said if I wanted to order something to eat I could but I mentioned I ate already. I mentioned I was on a date and proceeded to explain my blog. Apparently, he got a bit nervous after I told him about my blog. He continued asking more about the blog and mentioned he used to live in West Virginia, and that there’s not much to do there. I then offered that he could be my West Virginia date. I didn’t think he would agree, but he was completely down, he told me what we would do.

We continued talking and getting to know each. Then he tried to get me back to his place, but I responded in disgust that he was trying to get in my pants already. He apologized profusely, saying he wasn’t trying to hook up with me. We decided to go to another bar instead.


He opened his car door to drive me to the bar next door, I could tell he was trying to impress me after trying to get me back to his place. After we got a drink at Harry’s he offered to take me back to my Airbnb. As he opened the car door for me; he went in for the kiss.

He kept saying there was something between us, I’m not sure what was between us but there was a definitely something. We made out in the car for a while parked outside the Airbnb. After I said goodbye, he insisted I let him know how the dates for the following day went. I didn’t think he’d want to know about them, but I was glad he was completely comfortable with my blog and all my planned dates. I’m sure he’s probably reading this right now (hey Mike lol!)

He was the first guy I’ve kissed on this journey and he is also the first guy I planned to meet in another state. We have already picked a date for us to do in West Virginia. Stay tuned for how that date goes!

Date #3 – Richard

I matched with Richard on Bumble and I messaged him asking for places he recommended for me to visit. He actually had a lot of suggestions including a sex club that he apparently accidentally walked into one day. I asked if he wanted to join me somewhere besides the sex club, but he wasn’t going to get off work until much later. We instead agreed to meet for breakfast the next morning. I woke up that morning and saw I got a text from him at 2:30 am.

I figured he had a super late night at work and wanted to make sure I knew he was going to stand me up. We planned to meet at 9:30, but hours passed and I didn’t get a single text from him. I was starving so I decided to go eat by myself. He texted me around 2:30 apologizing. He apparently was a police officer and found a bunch of drugs in a car and didn’t get home till 5 am. I was completely understanding and hearing he was a police officer made him 10 times hotter, so I forgave him quickly. He promised to make it up to me if I ever came back to Lexington.

Date #4 – Ryan

Back in April, I wrote a post on Reddit in hopes of finding more dates. Ryan was one of the guys that filled out the application on my website. Once he applied I emailed him my number, saying I would like to go on a date with him. He texted me and we figured out the details on when I should visit. We texted every once in a while to check-in, until the weekend came. I’m always a little skeptical on if a guy will follow through on a date so I was happy he was still following through after 4 months of waiting.


We decided to go horseback riding at Kentucky Horse Park. We talked as we filled out the waiver and waited to get on our horses. The horseback ride experience was a bunch of horses in a line walking around the park. My horse was in a bit of a mood so he was walking a little slow. After riding we walked to the gift shop and I bought a shot glass. We sat down outside and Ryan was rubbing his eyes and admitted he was allergic to horses. He picked horseback riding and he’s allergic to horses. This wasn’t an unusual decision for him because he owned a dog when he was younger even though he’s also allergic to dogs.

I’m allergic to cats so I agreed he should go home to take his allergy medicine and try and recover. I asked if he wanted to eat dinner later in the day once he recovered. I figured I could just ask Mike or Kyle if anything, so I would be fine if he didn’t think he would be up for it. In the end, I didn’t up get dinner with Ryan, and Mike & Kyle couldn’t join me for dinner, but I think I had enough dates for my weekend in Lexington.


In Colorado, I secured a date in less than 24 hours. I was also stood up in Oklahoma and Lousiana. Dating is a big rollercoaster full of people ghosting and standing you up, but there are also those moments when you go on fun dates and have great conversations and connect with strangers. Going on three dates in Lexington, Kentucky definitely broke a record for me. Hopefully, there are more 2nd dates or 3rd dates in my future.

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