Dude, You're Making the Rest of Us Look Bad

Boston Magazine has a really long profile on Red Sox owner Jon Henry and his new fiancee. First off, much respect to him for not just dropping the "I own the Red Sox" line. While I'm sure that'll get you lots of action in this city, you'll get exactly the kind of girl you deserve if that's how you try and pick up women. Instead he went with the heartfelt email route, which also works well if sent to the right girl. Sent to the wrong girl, however, and you've simply given her and her girlfriends ammunition on you. But I guess you don't become a billionaire without taking some risks along the way.

Personally, I was never the love letter type. For me, it was the classic mix tape method that worked best. I shudder to think how many mix tapes or CDs that I made for various women are floating around. "I'll let U2, Vertical Horizon and Brian Adams say it for me." (Ed's Note: Jesus, no wonder those relationships failed.) But, I can't keep living the lie so now seems as good a time as any - for most of the ones I gave out in high school I used the exact same playlist. Sorry, ladies. I had found a mix that worked and I kept it.

I bring all this up because the new soon-to-be Mrs. Henry happens to be just a year older than me. Look, Mr. Henry, I'm happy for you. But, I can't compete with you and your buddies. I can write a nice letter, sure, but I can't bring a girl on my yacht and sail to South America. Nor can I arrange helicopter rides or have sweet seats at Fenway available whenever I want them. So, I just need you to make this marriage go the distance. There are only so many single, attractive ladies in this city and the last thing I need in my way is a billionaire and his buddies going after the same age group as me.

-Now, from the "on the other hand" files:
There are times I truly miss being in a relationship. You know, having someone to share that intimate connection with. Then I see the trailer for Ghosts of Girlfriends Past, realise if I had a girlfriend she might make me go see that and the feeling goes away. After that, it's Madden '09 time.

-While we're discussing relationships today I'm going to offer a ruling in honor of my amigo Nick: I don't care if a girl has packed a bag and made plans to stay at your house for the night. I don't even care if she's already changed into her pajamas. If, during an epic 3 overtime game in one of the best NBA series ever, she rolls her eyes and without a hint of sarcasm or ball-busting asks "This is going to be over by the time Private Practice starts, right?" you are, in fact, allowed to send her home. The trains run until midnight.