When First Dates Become Laughably Bad

We all have that one bad first date story whether it’s our own or someone’s we know. So, in honor of full disclosure, let me tell you one of my own.

One night some seven years ago, I went out on a first date with a cute guy I met online who was in the San Francisco Bay Area from Los Angeles for a few days visiting friends. We had down all the requisite pre-meeting things: we chatted for hours for a couple of days, exchanged pics, and had grown to like each other and naturally wanted to meet in person. He was totally cute with his longish, dark brown curly hair and beautiful dark brown eyes and great smile. I still wanted proceed with some caution as I had learned before, pics can be deceiving; but I was willing to be optimistic.

Things being as they were a few years ago, I didn’t have a car and Oliver was from out-of-town visiting friends and didn’t have a car either, so he borrowed his friend’s to take me out. Oliver arrived at my place and my along with my roommate opened the door to his knock in some surprise to note that I had hit the jackpot in finding a guy who was every bit as good-looking as his pic and even as tall he claimed to be in his emails. Things were off to a good start. On the drive into San Francisco, we had a drive full of ease and laughter, talking just as easily in person as we had online. Could it be? Had I actually found someone worth getting to know? It had seemed so. For dinner, we had played things low-key and went to an all night diner and continued chatting while we ate as if we had known each other longer than a few days.

We left the diner and drove up to a point at Twin Peaks to look out over the city on an uncommonly clear San Francisco night. He stood behind me, wrapping his coat and himself around me to keep me warm and dry during the light drizzle and as the stars shined down on us, he kissed me. Sweet, huh? Romantic, huh? At that point, I would agree with that. We then made plans to drive north a ways to Sausalito to walk around and just hang out for a few more hours to make the night last.

And so we drove in the early morning hours through San Francisco to head out of the city until disaster strikes, the car breaks down in a little neighborhood affectionately known as The Tenderloin or more commonly, Lower Nob Hill. We look at each other and laugh, for who would expect for the car to break down while you’re out on a date, right? Well, we decided to just hang out in the car and intermittently try to get the car to crank. Some time later, I needed to find a bathroom. So we walked the neighborhood trying to find someplace still open at 3am that had a public restroom…no such luck. Now, most people would consider public urination a thing you’d only do in the woods camping or while drunk; well, I was neither, and when you’ve gotta go, you’ve gotta go. Now, I will give props to Oliver for not only trying to find a restroom for me; but in our failure in finding one, stood in front of me with his jacket spread to cover me from sight when I had no choice but to go outside in an alley.

Now, with that mortifying moment over, we went back to the car to try to get it to run. Again, our luck fails us. So, Oliver is left with no choice but to call the friend to tell him what happened and see if we can do something about the car. For over an hour, Oliver called his friend with no answer; luckily, Oliver didn’t stop trying and the friend finally woke up and answered his phone. He sleepily told us he would call AAA to come tow us and would call us back once he got it squared away. Unfortunately, what said friend didn’t know was that the cardholder had to be there with the car when the tow truck arrives. Enter next problem. Oliver’s friend had to borrow his roommate’s car to drive from San Jose to come get us and drive me home about 30 minutes north of San Francisco. Being the good friend he was, he drove up to come get us and at 5:30 am, I arrive home after a most laughably bad date.

Now why would I consider it laughably bad? While I admit that the first half was great, sweet, fun, and romantic, breaking down in a questionable neighborhood at 3am, peeing in an alley pretty much in front of your date, and waiting about an hour or so for said date’s friend to answer his phone and pick us up and drive us home pushed the night into laughably bad territory. Do I blame Oliver? Nope, not a bit. Did I talk to him again? Yes, later that day and even for some time afterwards. Did I see him again? Again, yes. We saw each other again a couple of months later and had a much shorter and slightly less uneventful time during daylight hours. I haven’t seen or heard from Oliver in about 6 years; but just for the humorous aspect of our first date, I’ll remember him fondly for years to come.

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