Adventures in Dating #2: Big P*ssy

I'm going to skip straight to the top of my list of bad dating stories for installment #2, because let's be honest, I'm probably not going to complete many more entries in this series before I grow tired of it and decide it's not really that interesting. So, easily far and away the worst dating experience ever was with a guy we'll call Tony because of his surprising resemblance to a character on the Sopranos. (I actually have forgotten his real name at this point.)

I was living in Boston's North End at the time, and was walking to the grocery store one day when two guys in a car pulled over and a guy hopped out and asked me directions to somewhere. I gave them to him, and then he said I was cute and asked for my number. I had just broken up with my long term boyfriend earlier that year and still hadn't really re-engaged into the dating scene, so I decided to give him my number. I figured he wouldn't call, or if he did it would be good for me to go out with someone and reacquaint myself with dating life after 6 years off the market.

A few days later he called and asked if I would accompany him to a friend's Christmas party. I reluctantly agreed, not entirely comfortable with going to a party where I would not know a soul as our first date. (To this day, I refuse to go to parties with guys before I have had a chance to get to know them, for this very reason.)

During this first call, he told me a bit about himself, like that he was a real estate developer and was a few years older than me, in his mid-30's. (Later he would describe to me a business that he owned that made predictions of who would win football games and other sporting events. I'm pretty sure his actual job description was "bookie.")

So, the plan was for us to meet at the apartment of one of his friends who lived near where the party was taking place. I arrived there without any real trouble, and while his friends were getting ready in the other room (or maybe they were having sex...it was all very shady), Tony decided to teach me how to play craps. He also asked me if I got high, and I said I did not. He claimed he didn't either, but every 20-30 minutes or so he would walk into the kitchen and I would hear the telltale bubbling sound of a bong hit. I could also SEE the reflection of both Tony and the bong in the refrigerator. But, probably because he was so stoned, Tony was convinced I was none the wiser.

We ended up waiting a LONG time for his friends to get ready for this party, like well over two hours. Shortly before the friends finally came out of the bedroom and were ready to go, Tony suddenly attacked me in the kitchen, all hell bent on making out. It was very awkward. But even more awkward was a few minutes later when his friends came out of the bedroom and I was introduced to them, and Tony decided to announce to them that we "just had our first kiss." Um, WHAT? I was just speechless with how incredibly weird that whole thing was.

We left with the friends and headed to the Christmas party, where much to my relief I did actually know someone after all because a friend and her sister were at the party as well. That relief was short-lived, because Tony's guy friend who was clearly high as a kite on illegal substances of his own had dated my friend's sister, and decided to pick a massive fight with her. He eventually had to be escorted out of the party, and Tony had to take him home. Our first date ended there, but Tony had been very smart about things and had made arrangements with me very early in the evening, before things got weird, for us to go on a second date to the Celtics game the following Wednesday. (He apologized that the first date amongst all of his friends at this party, so he said in order to make it up to me he wanted to go to the Celtics game, just the two of us. I stupidly agreed.)

A few days after the Christmas party debacle, Tony called me to make arrangements to go to the game. He had to go to his father's company Christmas party first that night, so we might miss the first quarter, but he would come to my apartment as soon as he could and pick me up to go to the game. I was even more wary at this point, but I gave him my address. On the night of the game, I grew angrier and angrier as it got later and later and Tony was still not there. The game was nearing the end of the third quarter when I got a call from Tony saying he was walking down my street, and asking me to come meet him.

I headed downstairs, figuring we would walk to the Fleet Center from my house since it was only a few blocks away. Instead, to my great amazement, here was Tony wearing a suit, walking up my street rolling a suitcase behind him. I must have made a confused face, because his first words were "you're probably wondering why I have this suitcase." Uh, YEAH. "I've got a change of clothes, a bottle of wine, and some other things in here," he said. He wanted to change out of the suit before the game, so we headed upstairs (yes, very much against my better judgment) so that he could change.

When we got to my apartment, rather than changing clothes in the bathroom or bedroom, Tony changed out of his suit and into a sweater and a pair of jeans in the middle of my kitchen. I was at this point seething, as the Celtics game was about to head into the fourth quarter. It was obvious we weren't going. It was also fairly obvious what Tony's "other things" in the suitcase were intended for. I was having none of it, and told him that I did not feel well and would probably not be very good company. This was my not so subtle hint that he and his suitcase could skedaddle. And they did.

I thought that was the end of the saga, with a very uncomfortable situation narrowly averted, but I was wrong. A few weeks later, I received a call from a blocked number on my cell phone. Normally I would not answer such a call, but a guy I'd become involved with in the interim had to use a blocked number when he called me from work so I assumed it was him. Instead, it was Tony who was obviously drunk and with a rowdy group of friends. He began the conversation with "I just wanted to explain why I wasn't going to call you again." I started to say that it really wasn't something I had been wondering about, when Tony launched into a strange and rambly list of my faults. I was so shocked that I only remember two of the things he said: 1) I let my cat scratch up my arms like a crazy cat lady (okay...), and 2) "you obviously weren't going to put out." At this, his rowdy friends in the background cackled.

Yes, a man in his mid-30's was still using failure to fuck by the second date as a reason to dump a woman.

I was so surprised by this strange conversation that I really couldn't formulate a response. I think I said something along the lines of "you really didn't need to call to tell me this," but that was about all I could muster. We hung up, and only about 10 minutes later when my brain had time to process it all did the witty comebacks start flowing freely. But of course by then it was too late.

A year or two later I ran across his profile on an online dating site, and felt a twinge of sadness for all those women who would be enduring similarly strange and awful first and second dates with this dweeb.