Regrets?

So one of my biggest things is to not regret things. Could be a bad quality, I don't dwell on the past, but I like to think I learn from it and it has made me who I am. For better or for worse.

Well there was this one trip, and this one girl, and this one regret, that to this day I still wonder about. Was laying in bed the other night, and for some reason it came up. This is the story of that great weekend as I recall it now, almost five years later.

New York, Dave Matthews, and the girl

If you don't know already, I'm an avid Dave Matthews Band fan. I don’t quite compare to DMB fanatics of course. For me, however, six concerts is pretty good. Well, three of those concerts were packed into one summer. It was a pretty great summer, the summer between my junior and senior year of high school. The way it all worked out is a story in itself.

I lived in South Boston at the time. The whole big city thing was new to me, and I had no friends in the city. The second semester of my junior year of high school had been spent at a boarding school hours away, and none of my friends from school lived in the city. I spent most of my time at home, or just riding into the city and exploring. I learned to appreciate the city a lot.

The summer gave me a good bit of free time. I spent a while visiting family in my home state, and while I was there I went to my DMB show number one for that summer. That was my fourth, and while not the best was still a great time. I remember riding to the show with my friends, possibly a bit drunk, bit other things, and walking from the car in the parking lot barefoot to the grass on the hill for the concert. Good times. The set list was mediocre, but the time with the people is what mattered. Dancing in the grass, singing to the music, and just having a great time.

Well the rest of my summer was spent at home, in Southey. I spent about half of my time at home and half in the city. Ended up talking my brother into buying tickets to my second Dave Matthews Band show for the summer, and we ended up taking our sister and his wife. Yet another great show. The Fenway Park concert, which is actually recorded and up for sale. We had great seats, and going to DMB shows with family was always a great time for me. Plus, I had never been to Fenway Park for anything, so getting to watch my favorite band while sitting in the field was pretty cool.

My third show this summer was a mini music festival, and one of the most memorable weekends I have had in my life. It was the end of the summer. During my explorations of Boston, I discovered the Berklee School of Music. Music has been one of the few passions of mine, and while I'm not quite skilled or dedicated to become a professional, I felt compelled to see what this place was all about. Did a five week summer course, and while I was there for my audition I met my buddy Jona. We both were DMB fans, and became great friends pretty quick. Towards the end of the summer me, him, and our friends Bob and Rob went to NYC for the best DMB Concert I have seen to date, and one of my top weekends ever.

We were only down there for a weekend, so my first time in NYC was not really about the sights. We stayed at this really nice hotel, not even 3 blocks from Times Square. It was awesome. We went out about 11pm, regardless that we were going to the show around noon the next day. Standing in Times Square was pretty awesome. We checked out some stores, ate at a pretty tight little restaurant, and spent a few hours just exploring. I still remember ending up about 50 blocks from our hotel just by exploring, and somehow getting a cab back up to times square and finding our hotel. It’s crazy how we didn't get lost.

The next day we drove over to Randall's Island. I don't even know how to describe what I remember to someone who hasn't been there. We parked in a baseball field or something, and in the field where the show was to be held was a side stage where throughout the day a bunch of bands played. We made random friends, had beers among other things, and had a great day. The view was pretty great too. I mean, you’re on this island right in the middle of NYC. It’s a big field with water on three sides, an abundance of trees, and then just across the water these huge, shining buildings. It only got better at night, and that’s when the real fun started. I can't count how many times I watched the DMB Central Park concert on DVD when I was younger. Central park had shit on this. The buildings were much closer, the crowd may have been half as big but 50,000 compared to 100,000 isn't something you can really describe. The set list was 10,000 times better, and not only did Warren Haynes play Cortez the Killer, we got #41 with Bela Fleck & the Flecktones (If you’re interested to see how epic this set list was, check out this LINK).

Well the show was the best show I have been to, Ever. Not just DMB, but of all the maybe 50 various concerts I have seen, that was the best.

The next day was pretty cool, we did a bit of shopping and then headed to Long Island. We hit the beach, and either that day or the next we headed home. One of the best weekends ever, with some of my best friends ever. A weekend I will never forget, because its times like these that have made me who I am.

Then there was the ferry from NY to CT. It was probably a two hour ferry ride, and my friends and I had this hobby of scaring people. We found a booth next to a window where we could walk by, and we did, but upon leaving the view of the family at the booth I stopped, turned around, and jumped out at them. They all jumped up yelling and we ran off laughing. My friends ran one way and I ended up running around to the rear of the ferry. 

I was going to keep going and run around to find my friends, but there was this girl by herself at the back of the ferry, obviously my age, having a cigarette alone. I asked if I could bum one off her, and seeing that she looked down about something I asked if she wanted company. We talked for maybe ten minutes, but within five this girl was telling me she wanted to break up with her boyfriend (He lived on the other side of the country and was cheating on her), and for the rest of the time we just talked about each other. For a high school kid, especially with how I was about girls then, I'm still pretty proud of how I handled this situation. 

Let me back up for a minute though. This girl was gorgeous, and I don't think I have met a girl in person that was as good looking as her before then or up to this day. Like, if I had to choose between Marisa Miller and this girl, I would have chosen this girl.

Anyways, I guess my friends had gotten curious to where I had gone, and ended up finding me. It's never good when three friends in the mood to fuck with people find their friend talking to some hot girl instead of having gone to find them. They instantly decide to cock block the shit out of me, just because. It sucks, and I still don't know if I should regret it or not. I mean, what is there to regret? It's not like I could have done anything... right? 

Wrong.

We ended up pulling into port as we were parting with this girl (she had to find her friend), and when we went down to our car her and her friend were parked right next to us. I came up with a great idea and asked them if they would give me a ride home. They said yes, even after I told them I was joking and that it was over an hour out of their way. They said yes. That should have been enough for me to know, right?

Well, I guess the fact that back in high school I was horrible with girls, combined with the fact that I thought I just got cock blocked (I have decided since I wasn't, this girl was smart), must have killed my confidence that day. Almost two hours in the car with these girls, they drop me off and even come in to "use the bathroom". They hang for a few awkward minutes, and I don't even get up the balls to ask for their number. So yeah, maybe I should regret it. But hey, I learned a good lesson- A girl that hot should never be brought around friends, no matter how good of friends they are...