How to Hang Out With Your Boss Outside of Work

When you’re a few weeks into your internship, you probably feel like your supervisor is just a friend: you know her coffee order, are in constant communication with her, and, let’s be honest, you may even see her more than you see your own friends. But of course, you’d never see her after hours… or would you? Between the occasional work dinner and that office-wide softball tournament, seeing your boss outside of work is becoming more common. As excited as you may be to see your supervisor in a more social setting, it’s not as stress-free as you’d think. What should you talk about? Is he or she still your superior, or an equal? Relax, collegiettes; we’re here to help! Check out our guide to seeing your boss outside of work.

1. Dinner

Instead of running to get your boss lunch, the two of you are actually eating together. You’re probably not grabbing dinner one-on-one, but a work dinner is a big step from eating at your cubicle! After scanning the menu and finally ordering, you may be at a loss of words. What are you supposed to say to your boss? Devouring that breadbasket won’t completely save you from small talk, after all.

According to Dan Schawbel, author of Promote Yourself: The New Rules For Career Success, it’s important to build the conservation around both professional and personal topics. “Talk about sports, the news, and hobbies so you can build a stronger relationship with them,” says Schawbel.

Once you chow down on that yummy entrée, the waiter will slip you and your boss the bill. Yet another dilemma: who pays? “The person with the higher title and salary should always offer to pay for dinner unless it’s their birthday,” says Schawbel. “I would let them pay because they are in a better position to do so. You work for them, so it’s a nice gesture of them to offer.”

Whether or not you think your employer will pick up the tab, don’t splurge on the surf and turf when you order your meal; you’ll feel uncomfortable if your boss ends up paying for your expensive meal. Just remember to thank your boss for the dinner if he or she does end up paying!

2. Drinks

If you’re of legal age, grabbing a post-work cocktail is nothing out of the ordinary—it’s called happy hour for a reason! But instead of sipping on mojitos with your bestie or that cute guy you met last week, you’re enjoying a well-earned drink with your boss and coworkers. Unlike grabbing dinner with your boss, the conversation in this scenario should be less formal. “If you go to drinks with your manager, you can be more casual and you should talk about more personal things,” says Schawbel. We’re not giving you permission to give your boss a crash course in your latest boy drama; however, asking your supervisor what he or she is up to this weekend is a great conversation starter.

Unlike dining with your boss, it’s okay if you pay for his or her drink. “It doesn’t matter who pays for drinks, because typically if you buy the first drink, they will [pay] for the second,” explains Schawbel.

While an office-approved happy hour sounds great, what’s a collegiette to do if she’s underage? Whether or not you have a fake ID, don’t try to drink at this soiree if you’re not 21 or older. “Your management could get in trouble, which means you would get in trouble,” warns Schawbel. So does that mean you have to miss out on all the fun? Not necessarily. “You should still go for the networking aspect unless you are required to be 21 years old to get into the bar,” advises Schawbel. So instead of trying to sneakily order a glass of wine, opt for water or soda and focus on getting to know your boss and coworkers.

If you are of age, don’t take this as an opportunity to get drunk with your coworkers. “If you will be drinking alcohol, make sure your first drink is soda or water to quench your thirst,” advises Judith Gerberg, a career counselor and director of Gerberg & Company, a career development organization. “Then you can sip your next drink.” Even if your boss is tossing back the martinis, play it safe and stick with one or two drinks, like Anna* from NYU did at her former boss’s birthday party. “I ended up mingling with her 30-something friends, calmly sipping one drink,” she says. Post-work happy hour is a great way to unwind, but you don’t want to be remembered for your drinking habits.