How to Survive a Sporting Event with Your Boss

As a follow-up to my recent piece, Tips for Summer Interns of 2013, I have been asked to provide pearls of wisdom on surviving a sporting event with your boss.

As an international bon vivant, hopefully I have put something in here for everyone – well almost everyone.  If you’re going to a hockey game, it’s time to look for a new boss because it means he’s at the bottom of the food chain and there’s no point hitching your wagon to that star.  Regular season hockey games are for analysts and shitty brothers-in-law.  On a trading floor, it’s almost impossible to even give the tickets away.  But then again, we work in legitimate cities with real sports.  So if you are in Detroit, feel free to disregard.  But if that’s the case, you need a completely different set of survival tips right about now anyway.

Going to a sporting event with your boss (and presumably clients and colleagues) is a complicated, nuanced, and often conflicting minefield to navigate.  If it was so easy, then everybody would work at Goldman Sachs.

To the point:

1)    If it’s a weeknight, wear what you wore to the office.  If you show up in skinny jeans, you’re obviously not busy enough.  If you are at a Miami Heat game, wear whatever you want because you don’t have a respectable, IRS-abiding job anyway.

2)    No photos. No tweets. No Facebook posts. Act like you’ve been there before.

3)    Bring a date, but not if she’s needy or insecure.  (Odds are that she is.)  First of all, most girls aren’t huge sports fans to begin with.  But more importantly, she’s going to feel like a 3^rd wheel when you’re talking with clients, colleagues, or your boss.  And if you prioritize coddling her, you are going to look like an unprofessional, pussy-whipped dickhead.

4)    Stop checking your Blackberry. You both know that your boss is more important than you are, so if he’s not checking his, why the hell do you need to check yours?  It can wait.

5)    Don’t wear a jersey… unless it’s a fútbol match.

6)    If it’s a big game, and you’re on club/box level, do a lap. You never know who you might see… unless it’s a Mets game; no one gives a fuck about Bill Maher or Keith Olbermann.

7)    If a work rival is there, get him wasted and convince him that the drinks girl working the suite wants to bang him.

8)    Remember, in 50 years, no one will watch baseball.  It was invented when there was absolutely nothing else to do.  So be mentally prepared to make 4 hours of conversation.

9)    While passion is a good thing, if you didn’t have a poster above your bunk bed as a kid, stay neutral.  No one likes a poser, and only Asian kids can get away with conveniently being ‘diehard’ Manchester United or New York Yankees fans.

10)If it’s a cricket match (The Ashes?), don’t go unless you understand the sport.  Chances are, if your boss is there, he loves it.  And not even Meryl Streep could pretend to enjoy that sport.

11)Clients come first. Keep it professional. Usually, they leave early, and if they don’t, it means they have a free pass for the night.  In which case, you are required to show them a good time.  Don’t bother saving the Flashdancers receipt (Matt Defusco?); just expense the next three “date nights” at Jean-Georges.

12)Bring a joke. But don’t use it unless someone else tells a joke first.

13)Don’t be a sports douche.  Nothing is worse than canned, feigned sports knowledge. “Lampard saved the day, but I still don’t understand why Mourinho went with the 4-4-2.”  Fuck off.

14)If you’re at Wimbledon, do not drink Pimm’s. You don’t want to be that guy who passes out on the tube home with grass stains on his trousers.

15)If there’s a good-looking girl, get her drunk, preferably on Pimm’s.

16)Talk about work when prompted, but otherwise, this is a chance to showcase your personality and find a connection.  Seriously, it’s not that hard: travel, cars, wine, family, and sports. But drop the wannabe trader-speak and avoid saying “yours” every time some douchebag (Vinay Jayaram?) mentions Duke.

17)If you are the office rock star, wear the latest outfit from the John Daly collection.  When you get to Arthur Ashe Stadium, tell everyone you thought it was the US Open at Bethpage.

18)If you don’t have a girlfriend, bring one of the Puerto Rican secretaries as your date. If you have coke, don’t share it with her until after the match, or she’ll start talking about how much she likes anal sex in front of your boss’ wife.

19)Don’t forget to tell any work rivals that “everyone is going to Wiggles in Rego Park after Serena loses.” – Google it or ask Shahryar Mahbub.

20)Most importantly, your boss is always the benchmark of depravity.  If he’s sitting in first class on the plane to Hell, make sure you’re in the cockpit.