As a kid, I always pictured my first trip to Boston. That may seem like a strange dream destination for a five year-old boy from Atlanta, but when you love Tom Brady as much as I do, it’s not hard to see why Boston was the place to be. It had everything I thought a grown man needed at age five. A rich sports history, good food and an airport to come back to visit the fam when I got homesick. I had made up my mind, Tom Bra… I mean, Boston, here I come.

It ended up taking me 16 years to finally book my flight to Beantown and it turned out the reason for going wasn’t the New England Patriots starting quarterback — but we’ll get back to that a little later. I booked my flight with great expectations for my dream city and what I got ended up exceeding all those expectations as soon as I stepped off the plane.

In true Masshole form, I decided the best clothing to wear for my flight would be my “Free Brady” t-shirt, courtesy of the fellas over at Barstool Sports. To my delight, I was met with thunderous “Free Brady!” screams from three fellow Patriots fans not five minutes after stepping off my flight. Boston was everything I hoped for and more.

As my week progressed, I was able to experience just about every piece of the city I had fantasized about as a kid. My adult diet went by the wayside quickly. I think in the first two days I was up here, I had an entire pizza, a box of doughnuts, and at least one pitcher of beer. So good food: Check. Next, came the sightseeing. I took a tour of Christ Church in historic downtown Boston. I walked the entire length of Harvard campus (Side note. I got stopped by a gentleman while walking around Harvard Square. He asked me directions to one of the buildings on campus. I smiled and pointed him in the direction from which I was walking. I have absolutely no idea what building he was looking for or where it was for that matter, but in that moment, that man thought I went to Harvard and I wasn’t going to be the one to tell him he was wrong. I apologize good sir. If you’re reading this, I hope a real Harvard student pointed you in the right direction). I saw the Basketball Hall of Fame out in Springfield, Mass and I even got lucky enough to catch a Red Sox/Yankee game at Fenway Park (Literally, nothing like you’ve ever seen before. There is nothing like this rivalry. The benches cleared halfway through the game and I though the stands were about to clear with them. There was at least one fight between fans a couple sections over from our seats. It was outstanding.). However the highlight of the trip was still to come.

By Wednesday, I had seen and played out every possible scenario of my Boston childhood dream except one. Watching Tommy Brady in Foxboro. Football season wasn’t technically for another month, but training camp had started a few weeks back. My fantastic aunt and uncle were kind enough to take me the night before so that I would get to see my hero in action. My feelings rolling up to 1 Patriot Place that stormy Wednesday morning mirrored that of an old Catholic lady approaching St. Peter and the Pearly Gates in Heaven (at least, that’s what I assume it feels like. After that comment, I may never know). Seeing TB12 take the practice field was one of the coolest things five to twenty year-old me could ever dream of. Practice lasted maybe two hours and the rain didn’t let up. I stood in metal bleachers in the pouring rain with shorts and t-shirt the whole time. It was great and if I had come to Boston at any other age it would have been the highlight of my trip. However, I wasn’t here for Tom Brady.

A while back, I wrote an article that discussed the weight of the decisions we all make. The center piece of the article was the choice I made in purchasing my ticket to Boston. However, I wasn’t in the place to reveal my reason behind going until now. To keep with the spirit of Boston, well South Boston, as local wiz kid, Will Hunting would say, “I had to go see about a girl.”

We had met two weeks before the close of last semester and they had been some of the best weeks I had had in quite some time. This wasn’t just a flash in the pan Judy or Jan. This is a one in seven or eight billion type girl. We’re talking star of the show type deal. The reason for the season and every other cliché reference you can think of. She had earned an apprenticeship at a theatre in Western Massachusetts for the summer and she would be leaving almost immediately after the semester ended.

It was too soon start anything serious. We had just met and now she was going away for the summer. It wouldn’t have been right, but that didn’t mean I was done. The gears in my head started turning and slowly but surely a plan started forming. The preview of her show was Aug. 11. Summer camp ended Aug. 5 and classes didn’t start back until Aug. 15. I could make it. I had to make it, so I did. I bought my ticket to the show and then I bought my ticket to Boston.

That was back in late May or early June. I spent the next two months anxiously awaiting my trip. When that Thursday finally came, to say I was nervous would probably be selling it quite short. I really had no idea how this would turn out but I knew I would regret it every day of my life if I didn’t go.

Boston showed me a great time. The city was everything I wanted it to be and more. I got to experience American history first hand and eat some of the best food one could find in the northeast. I got to experience the greatest rivalry in all of major sports and I even got to my childhood hero take the field on his home turf. But the highlight of my trip wasn’t confined to the city limits of one of America’s greatest cities. The highlight was the smile of girl in western Massachusetts.

It may have been a short exchange due to the time constraints and that two hour trip back, but those were ten or twelve minutes I wouldn’t trade for anything. That includes tickets to Tom Brady’s next Super Bowl.

I must have imagined my first trip to Boston a thousand times growing up, each trip getting grander and grander as time moved forward. I had a vision of the kind of joy the city would bring me and the lasting legacy it would leave on me when I left. I never imagined anything like the week I just had. I don’t know when I’ll get to go back but whenever it is, it’ll be hard to top the week that just was.

Also, this article wouldn’t be complete without a huge thank you to my cousin, who for all intents and purposes, made this possible. I wouldn’t have been able to make it out to the play or even have a place to stay if it wasn’t for him. I owe him more than that Red Sox/Yankee game.