It was so windy down by the Back Bay Boathouse that there were hardly any sailors out on the river. The water was really rough and there were big white caps. Probably too windy to be sailing with little boats, but not so bad that the expert sailors couldn’t handle it.
I certainly figured I could handle it, I mean, it was just a little river with little waves, how bad could it be? They used different flags for different weather conditions. This particular day was a red flag day. My kind of a day.
Anyway, I think my rating wasn’t high enough to go out by myself, so I had to find someone to go with me. It didn’t matter if the person knew how to sail; I just needed some extra ballast, (that’s sailing talk for extra weight). I started looking to see if anyone was around and there weren’t really that many people there, so I went back to the park area in front of the boathouse to find someone to take sailing.
I finally found someone that I could ask; I saw this really pretty girl in her early twenties sitting there reading or something. Somehow, I seemed to have this sort of radar for certain types of people. I don’t know why, but I was always able to find cute, single girls, who were just sitting there, minding their own business. So, I just walked up to her and made pleasant conversation for a few minutes, like, “So, what are you reading?” – that kind of stuff.
We hit it off well enough and then I asked her, “Hey, do you wanna go sailing? I’m an expert sailor and you will have a blast.” She sort of hesitated and didn’t really know if she should, plus she didn’t know me from a hole in the wall. I don’t think she wanted to go, but I kept telling her how much fun it was going to be and how it was time in her life to go on adventures and be swept away by knights in shining armor. In my case, it was more like preppy guy with alligator shirt.
She fell for my enthusiasm and, finally, after enough of me trying to convince her, she broke down and said “OK”. I told her not to worry and that there was nothing to it and that I never have crashed or tipped over or anything like that. I told her that it was a no-brainer basically and that she could trust me and that everything was going to be fine.

We walked over to the boathouse and signed in and picked up our life vests. I had my new sailing partner and we were all set. It was REALLY windy out, but I figured it would be really fun, and I knew for sure that we were in no danger. I had sailed on that little river for over two years and at least a hundred times, and I was for all practical purposes a bona fide expert. So we got in the boat and put on our little life vests and set sail.
The wind was really gusty and in a few seconds we were flying. My new sailing friend looked like she was having fun, and I said, “Hang on, we’re going for it!”
Everything was fine for a while and it was a total blast. I taught her how to lean back and which ropes to pull and how to come about and duck your head so you don’t get hit while the boom swings across the boat. I showed her how the rudder and tiller worked and about the tell tales and about how different angles achieved different results with speed. I told her about port and starboard and used fancy nautical terms like beam reaching and luffing. She was very impressed. I was the captain and she was my crew. We both knew our roles and it was a simple plan to understand.
I noticed there weren’t any other boats on the river and I thought that was odd because it was in the middle of the day and it didn’t really seem all that windy. Just because it was a red flag day and just because the waves were really high and crashing all over the front of the boat and were white caps, that didn’t really phase me much. Remember, I was an expert sailor and this was a piece of cake. About ten minutes into our sailing expedition, a giant gust of wind came out of nowhere and tipped us over. It all seemed to happen in slow motion because I could feel the immense power of that wind and we both were leaning really far over the edge of the boat to try and keep it from tipping over. But the wind was easily ten times stronger than we were and it had a mind of its own. I should’ve let go of the main sail but the wind just came out of nowhere and caught me by surprise. We were no match for the wind that day and we just tipped over into the rough, red flag day water of the Charles River.
The water was super Rough and it felt like we were in the middle of the ocean. One second everything was cooland then in an instant we were thrown into the water and bobbing up and down trying to hold on to the side of the boat. It was always like that for me in life; one second I’m good and then out of nowhere I’m thrown into a situation that I have no idea where it came from or how to deal with it and it usually was totally embarrassing.

Unfortunately for me, these little boats were just a bit too big to stand on the centerboard and right them back up. At least if that were the case, I could have gotten us out that jam and even though we were totally soaked, at least I could have solved the problem somewhat. In this particular case, if you tip over with this particular sailboat, you also start to capsize and completely turn bottom up. That’s what happened, and now there I was, with this soaking wet chick I barely knew, hanging on for dear life.
It was like one of those scenes in I Love Lucy where she was in a crazy situation and it kept getting worse and she couldn’t get out of it. It was one of those scenes in life where you really just wanted to sneak away without anyone noticing. But I couldn’t. I was stuck with this perfect stranger who just glared at me like I was a total idiot. I bet she couldn’t believe she was stranded in this upside-down boat in the middle of total storm conditions on the Charles River.
I felt like a total loser and totally embarrassed, once again. This feeling was not new to me and even though it happened to me MANY times before, it still never got easy to get used to. It was a terrible, completely lame feeling of just being in the wrong place at the wrong time with the wrong person and not being able to quickly make an escape. It was an elongated temporary moment of complete bumming with no relief in sight.

I just looked at her and half smiled and shrugged my shoulders and was like, “Hey, this never happens. I’m so sorry. I can’t believe this. I don’t know what to tell you.”
It was a total catastrophe and, not only that, we had to sit there in the middle of the Charles River for about half an hour, soaking wet, with all our clothes on, clinging to the side of the wet, cold, dirty, stinky boat, until the stupid rescue guys figured out that we had tipped over and finally showed up to get us out of that stupid river.
She wouldn’t even look at me, and I was in one of those places in life where I just had to let it pass as soon as I could. I had to take the uncomfortable silence and grin and bear it. She was so mad at me and rightly so. It was all my fault. I had pulled her out of her little comfort zone. She’d taken a chance on a total stranger, and within ten minutes our lives had been literally turned upside down.

Finally, the rescue guys saw that we were upside down and they sent out the rescue team in their fast little speedboat.
They threw us a line for me to tie to the handle on the bow so that they could tow it in. Then we climbed into the rescue team motorboat and they zipped us back to the dock. This poor girl was so bummed at me for ruining her whole day, and she was kind of a shy, quiet type, so she couldn’t really yell at me and get it out of her system.
There was a big sign in the office of the boathouse that said basically that they were not liable for any accidents and that you had to agree to sail at your own risk.
As we were leaving, I sort of pointed towards the sign and half smiled and put up my hands like, “Hey, the sign says right there that you gotta take your chances when it comes to sailing here”…she just looked at me like I was a total loser and stormed out of there while her sneakers were making that squishy sound shoes make when they’re filled up with water.
I yelled over to her when she was about 50 feet away and said, “so does this mean that we have to stop seeing each other?”