A Comprehensive Guide to Getting Drunk With Your Boss

Don’t end up getting fired because of one (un)happy hour. 

Imagine yourself on a wild romp through Europe, rife with breasts, bongs, and a ton of booze. Now picture your boss by your side: The pleasure factor diminishes significantly. In the upcoming Unfinished Business, Vince Vaughn brings his associates, Tom Wilkinson and Dave Franco, on a debauched business trip to Berlin. While you probably won’t end up at international sex fetish convention with the person who signs your paychecks any time soon, chances are you’ll be grabbing beers together in the near future.

Unless you abstain from alcohol for religious or sobriety reasons, you should join in the fun. Corporate consultant and former stockbroker Mark Jeffries is pro drinking with colleagues and superiors, pointing out what we’ve known in our heart for years: “Being social is an essential part of climbing the ladder.” But it’s imperative that you don’t get completely trashed. “You could screw up your whole career,” he warns, advising to avoid losing control and discussing touchy subjects like politics, religion, pay, and bonuses. (Or blurting out that you’ve always wanted to sleep with his daughter.) We know that’s easier said than done, so here’s how Maxim thinks you should get drunk with your boss in every possible situation that could arise. 

When you’re at the dive bar down the street from your office.

Dive bars are historically where we’ve made some of our more questionable decisions, so be on your guard here and be prepared to leave early. Order a round for the group early in the night so you can slip out when Lisa from marketing decides that she JUST WAAANNS TO DAAAAANCE. Your boss should, under no circumstances, have to watch you dance.

When you’ve all had a stressful day at the office and just want to pound your favorite drink, but you have plans with your boss.

It’s not worth it. If you’re a whiskey man, Jeffries suggests ordering beer, or vice versa. Having a drink that’s not your go-to will force you to slow down, because guzzling is never a good look. 

When you want a raise or promotion.

It may seem tempting to try to sweet talk your boss about getting ahead once he or she has a few drinks in them. And sure, everyone’s going to be more comfortable and laid back than if they’re in the office. Jeffries advises against this in favor of “non-business bonding,” which will be more memorable in the long term when you’re actually up for that raise. Nobody will be able to resist giving you more money after watching your karaoke rendition of “Total Eclipse of the Heart.” 

When you’re on an international business trip.

There’s an added level of pressure here, because you’ll likely be meeting with clients rooted in an entirely different drinking culture. Jeffries used Russia as an example, where they toast with vodka frequently throughout the meal. Going along with it is not only fun, but will strengthen all your relationships. За здоровье, as they say.

If you somehow end up at a strip club together.

Act like a gentleman — and never offer to buy your boss a lap dance.

When your boss is totally wasted.

Help him or her get in a cab or back to their hotel, then never speak of it again.

Photos by 20th Century Fox