This is my first and only Match experience in Chicago.
He was somewhat cute, seemed intelligent, and had pictures of himself with friends (a definite must to claim normalcy). His messages were a perfect mix of information and questions to keep the conversation going, and he seemed like he had a great sense of humor. So after a few days, he asked me to meet him at a pub for a drink. We lived on complete opposite sides of the city (~15 miles apart), and he picked a place that was very easy for me to get to, even though it was not easy for him. There was no awkwardness when we arrived, so we decided to have dinner too. Conversation was great. As we got close to dessert, his phone would not stop ringing (it was on vibrate), so he asked if it were ok if he checked who was calling. It was his mother, and he again asked permission to call her back since she had called so many times–all perfectly reasonable things to do. He called her back, mostly listened, and then said he would call her back tomorrow. He then excused himself from the table and was gone for over 20 minutes! He came back looking a little pale, said everything was fine, but was much quieter the rest of dinner. He walked me to the bus, asked if we could see each other again, and kissed me goodnight. Other than the long, inexplicable disappearance from the table, it was a great first date.
We planned for drinks only as a second date since we were both extremely busy during the next week. This time we picked a place that was centrally located between us. He immediately explained to me what happened at dinner. His mother's frequent calls were her calling to tell him that she had Stage 4 cancer with a life expectancy of about eight months. He then proceeded to cry uncontrollably in the bar, and I had no idea what to do. We decided to call it a night and agreed we would reschedule for a better time. It was not the right time for him to get to know someone new. He needed to spend time with his mom.
So fast forward to about two months, after no communication, he called me to ask if he could try for a third time to show me a better first date. His mom had found out that he was on a date when she told him and insisted that he still live his life as her "dying wish." That is not exactly easy to say no to, and since he was such a gentleman and extremely respectful about everything so far, I agreed. He asked me to meet him for dinner at one of my favorite restaurants and then to go to a theater show nearby. Dinner–unbeknownst to me–was his birthday celebration with a few of his friends. It was a bit awkward, but they were all nice people and seemingly had no delusions about our dating status.
Following dinner, the two of us went to the late show alone. Being March in Chicago, the weather was comfortably in the 50s when we arrived, but when we came out of the show 90 minutes later, there was a freak ice storm. There was ice everywhere to the point that police were closing roads, taxis were no longer driving, etc. Since the show was late and the ice was so bad, the train also had already stopped running. There was no way I was getting home (~15 miles away) until the roads were treated.
He only lived a few blocks away, so we went to his place to wait for the roads to be cleared. His roommate was home, and we hung out with him for a while. I was freezing (I was not dressed for the unexpected 30 degree weather), so we went into his room to get a sweatshirt for me. I sat at his desk looking at some pictures that he had displayed, and when I turned around, he had his pants completely off. And I mean both boxers and pants off–shirt and socks still very much on. Note, at this point in time, we still had only kissed maybe twice and spent a total of less than 10 hours together! But the worst part was that what I saw was not normal in any way! Normally I would never share intimate details, but I was so caught off guard and creeped out by what I saw, I had to share with my closest friends to confirm that what I saw was in fact not normal. This is how he was nicknamed the Yellow Bastard.
To say the least, being stuck there for a few hours was insanely awkward, and we did not see each other again.