Where to begin?

Last year, Jay got married and as best man it was my job to arrange a bachelor party of some kind. Now, Jay and I are not really into what you might think of when you think “bachelor party” and neither of us wanted to go through the motions if it wasn’t going to be any fun, so basically I had to get creative. I wanted to aim high, but I really didn’t want to screw it up, so basically I decided to punt two options to Jay and let him decide how much he wanted to risk.

Option 1 was the one I knew would be fun no matter how badly I planned it, and it was the one Jay ultimately selected. We would just get on a plane and spend a week in Amsterdam. I know what you’re thinking – a bachelor party in Amsterdam! You evil evil men! But honestly, we just did what Rick Steves told us to do, and despite spending the whole flight over listening to what our next-seat neighbor – a Marine on his way to Iraq, btw – would do in our situation, we managed to stay quite out of trouble. I don’t imagine they get a lot of bachelor parties at the Anne Frank House, but let it not be said that they haven’t had at least one.

Option 2 was the “creative” option – the one that seemed like it could be fun and different, but it could also have gone very very badly. If you are not familiar with the works of the great Weird Al Yankovic, this will make even less sense, but the idea I had was to hit the road from either Boston or Philadelphia and drive cross-country until we arrived at the biggest ball of twine in Minnesota. I figured we could find enough points of interest and roadside weirdness along the way to make a good trip of it. The pitfalls included the difficulty of planning such an adventure and the potential for the whole thing to blur into just a big boring week-or-so car ride.

As I mentioned, Jay chose Amsterdam, but it wasn’t as easy to decide as it would be for, well, probably you. It’s tough to describe the significance of Weird Al, but it should suffice to say that Jay liked the idea, and by not doing it there was some real potential for what-if regrets. Fortunately, I was already engaged myself by that time last year, so it looks like we’ve got the perfect excuse.

Looking back on the whole process, I have to hand it to Jay and his prescient decision-making. The truth is that I really didn’t do any planning for the Amsterdam trip, and although it really was fun anyway there is absolutely no way I could have come up with the itinerary that he created for this adventure. Not only do we have an excellent plan, but Jay has also arranged a secret boredom-destroying weapon: We will be accompanied on the trip by the skills of the legendary conversationalist and Weird Al afficionado known only as Deech. The crew complete, we officially head out in two days. This is our dumb story.