I had been set up for a first date with a really nice girl. My friend thought that we had a lot in common, and that she was very pretty, easy going and that I might just be the perfect match for her. He later told me how much he thought we were similar and that he himself at one point was interested in dating Tanya. Little did I know at the time, that this would end up a famous story of my most embarrassing and worst first date.
My Buddy Jack Found the Perfect Date for Me
My friend Jack was kind of a player in college, so it didn’t surprise me that he had aspirations of dating any woman within eye shot. Jack had met Tanya in school shortly before he was set to graduate and said that he had met Tanya on a few occasions at parties in New York City (NYC), but either he or she were with someone else each time they met. The two had chatted a little and were mostly acquaintances at the time.
Jack told me that they had met a few years later, when one of his girlfriends introduced her as a friend of hers. Jack recognized her instantly, but had to let on that they had never met before. Tanya had asked him to spare his girlfriend the truth, just in case, as she knew that his girlfriend was the jealous type. Jack agreed. He was a jokester, but knew this was one area, that he should just keep his mouth shut. Well until that day someone let it slip that they knew each other in college. Even though they had never dated, this of course was the end to that relationship.
Jack lived in and around NYC his entire life, like myself, and had a lot of connections. His family was well connected in the city, allowing him to get things done no matter the situation.
Jack and Tanya remained friends even after he split from his past girlfriend, and the two have remained friends for a number of years. Jack liked Tanya since she was easy to get along with and was nice to look at. He also thought that she was very smart and had a lot of interests like writing and biking. Which are shared passions of both Jack and I as well.
Jack and I worked together, and we hung out a lot after work before and we became good friends ourselves. Jack and I tended to joke around a lot, and have some healthy ribbing on each of our dating habits. We regularly did a lot of sports and partying together and he became like a brother to me. My own brother was a little jealous I think. Jack knew my tastes in women as well, and knew that I had a penchant for athletic women with nice curves and great lips. He told me he had the perfect woman for me to meet, and he didn’t know why he hadn’t thought of getting us together before.
The First Date
Like myself, Tanya was Italian, with dark hair and a nice olive completion. She came from a large family like myself and understood the culture of Italians in the city. She was very pretty and I wasn’t surprised that Jack knew her. I think he knew or knew of every single beautiful woman in the NYC area.
Jack told me about Tanya and about how great she was and a great catch for someone like me. I immediately asked what is wrong with her, but Jack assured me that there was nothing and that they were friends only for several years. Once I saw her picture and he told me a bit about her, I was in. So, he set Tanya and me up on a blind dinner date.
We met at a dinner club in the city that turns into more of a nightclub in the evenings. We met and I immediately felt comfortable with her. Initially we had a great date, she was beautiful, charming with a little bit of an attitude and smart. She could discuss about any subject and we never had any moments of awkward silence. As we had similar backgrounds and from what she told me, she reminded me so much of my family.
She told me that her father and family were well connected in town. I could understand this, as my own was also a big part of the community. We enjoyed each other’s company, had a great meal and I thought what a great sexy person Tanya was. Maybe I could make her my person one day. We finished up dinner and went for a little walk around the city. I felt like a young schoolboy with a crush as we held hands and walked the streets.
I asked her if she was up for continuing the date and if she wanted to go dancing. She said she did and we hit up a local dance club near my apartment. We had a great time dancing and flirting, and I thought you know, this is a really great date.
Tanya and I got a little drunk and started making out in the bar, and decided to go to my place to hang out.
The Follow-on and the Aftermath
We got to my place and had a little tongue wresting session, and rolled around the floor a bit, just playing with each other in a slightly more than platonic sort of way. Fortunately, we didn’t take things too far. At about 1200 midnight, my brother knocked on the door. I was surprised a bit, but this wasn’t atypical for him since he probably guessed I was still awake and probably didn’t know about the date.
I opened the door to see him and Jack with camera in toe. They walked in and saw Tanya on the floor, partially disheveled, and myself with messed up hair and wrinkled clothing. I didn’t register the camera at first and asked what was going on. Just then, my brother said, “How was your date with Cousin Tanya?”
I said, “What?”
Tanya said, “What?”
My brother and Jack busted out laughing and took a couple of snapshots in addition to the video, while running out the door.
“Holy Crap,” I said. Just then Tanya took off out the door, and ran down the stairs to the street. She chased after them but never caught them.
I had no idea, and neither did Tanya. Did these two set this whole thing up just to embarrass both of us and so they could get video footage of the whole thing?
I can’t believe that I didn’t recognize my own Cousin Tanya. I had no idea something this sinister was afoot. I had never put two and two together, but wondered why we had such a familiarity with each other.
Worst first date ever, and it was confirmed by my family. That is, my idiot brother and Jack who was like my brother. I didn’t even know that these two talked often, but they set me up good? It turns out that Jack and my brother went out together to a party that night and Jack showed the picture of Tanya to my brother, who instantly recognized my cousin. Tanya is my mom’s bother’s daughter who has a different last name. So, Jack never made the connection back to me or my family.
When my brother saw the photo, they rushed over to stop us, just in case. My brother said that the camera was just a bonus.
To this day, these bozos use the video to blackmail both of us in to not telling my parents, or hers (a.k.a., my Aunt and Uncle).
After I settled down in a week or so, I saw some humor in it. Well, in a sick brotherly kind of way. Sick burn really. Tanya took a long time to come around. She was bit pissed at Jack, but eventually understood the humor in it. It took a bit of forgiveness on both of our parts.
I hate to admit that I really enjoyed the date. And I now know why I was so comfortable with her.
Later Jack and my brother teased me, a bit and wondered if I had wanted to date anyone else in the family. “Kissing cousins” became the mantra from these two morons. I didn’t think Tanya would get over it, but she was tough and resilient as well. “After all toughness runs in the family,” I told her. At least she smiled and thought it was funny as well.
Family Matters
We both came to terms with what had happened, but we had a hard time looking at each other at family gatherings and reunions ever since that night.
