My Date at the Chicago Airport

I decided to fly standby for my Chicago trip. Standby flights can be very unpredictable. Going there I got on the first flight, headed back to Atlanta was a different story. I ended up spending the night at the Ohare airport and didn’t get back till Monday morning. There was an upside because I had a little mini-date at the airport. 


Waiting at the airport for hours as a solo traveler can get a bit lonely sometimes. So while I was waiting for hours on end I wrote a post on Whisper. Whisper is an app I use sometimes. It’s like Twitter, but anonymous. You write posts and people can reply by commenting below or messaging you directly. I’ve had some great conversations with people on Whisper and have even been on a couple of dates from people I have met on the app. My Colorado date was actually from Whisper.

While waiting at the Chicago O’Hare International Airport I posted this: 


I had a couple of responses. Some from people that lived near the airport and one from an older guy that I didn’t think was in my best interest

I finally received a message from Kelvin. He offered to come to my gate to meet me. This is an anonymous app so I had no idea what he looked like and he didn’t know what I looked like either. When he got to my gate he walked around looking for me and told me to meet him at the Starbucks across the way. 


I technically didn’t have a date in Chicago and this guy was definitely a refreshment after the weekend I had. He bought me a drink at Starbucks and we sat down on chairs. The conversation was natural as we got to know each other. Kelvin said he was in the army and I explained my blog in response. I admitted I visited a guy I used to date and shared all the details. He further explained his previous long-distance relationship and asked if that would be anything I would consider. After just a short interaction I could tell what a great guy he was. 

I argued this could be my Chicago date since I technically didn’t have the one I planned. He happily agreed so I had him fill out my postcard. 


It’s amazing how quickly you can connect with someone. Hanging out in an airport for almost a whole day is not my favorite part of traveling, but I always try to make the best of every situation. My 50 Dates in 50 States is more than just a fun challenge. It’s really about the experiences and connections I make, even if it’s just talking over Starbucks in the Chicago airport.

Leave a Reply