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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.


3. Work-Affiliated Parties

Though work and parties don’t seem to go hand in hand, you’re bound to attend work events over the course of your blossoming career. Holiday parties, anyone? You may think this is a great opportunity to have some one-on-one time with your boss; however, it’s imperative to bond with other employees as well. “If you’re at a work party, you should be networking with people in your group and not just staying by your boss’s side the whole time, which most people are inclined to do,” says Schawbel. As much as your supervisor may want to talk to you, he or she will also want to socialize with other coworkers. Not to mention, mingling with other people will help you in the long run—the more employers who know your name, the more likely they are to come to you with important projects.

What should you talk about with your coworkers? “Avoid topics like politics and religion unless you work for an organization that is dedicated to a political action or has religious underpinnings,” suggests Gerberg. Instead, our expert suggests talking about things you’re passionate about, even if they’re not work-related. Whether you’re a huge sports fan or a major film buff, don’t be afraid to share your interests and hobbies with others. You never know; you may have more in common with your coworkers than you originally thought!

Mingling with your coworkers sounds great, but what should you do when you’re talking to your actual boss? Schawbel suggests discussing both personal and professional topics. “You want to be casual. Talk about other things aside from work,” advises Schawbel. Since you’re at a work function, it’s impossible to avoid the nine-to-five chat, so try breaking the ice with industry-related news instead. Not only will your boss be interested by the conversation, it will also show them how passionate you are about the internship. All while keeping it casual? Sounds good to us!

4. Running into your boss at a bar

Since everyone loves to celebrate the weekend, don’t be surprised if you see your boss out on the town. You’re not the only one who’s secretly counting down the hours until Friday night! If you do bump into your boss while going out, skip the work talk. Who wants to discuss spreadsheets and meetings when Macklemore and Ryan Lewis’s “Can’t Hold Us” is blaring? However, we’re not telling you to talk about how much you drank at the pregame or how your ex is at the same bar. “You don’t want to make a fool of yourself or reveal details about your life that should remain private,” advises Schawbel. Instead, compliment your boss’s cute top or ask what he or she has in store for the rest of the weekend.

Though everyone is entitled to a fun weekend, it’s important to not model your night after Spring Breakers if your boss is right there. If you randomly ran into your boss, go easy on that cocktail you’re holding. Letting loose may seem like a good idea at the time; however, you’ll be embarrassed if your boss sees you stumbling around the bar… or worse! While a Friday or Saturday night may be the perfect time to meet some cute guys, save the DFMO for a night when your boss isn’t there. Gushing about that hottie from the weekend may seem like a surefire way to bond, but you never want to be that girl whose boss saw her locking lips with some stranger. Awkward? We think so.

5. Athletic Events

Believe it or not, you may find yourself sweating alongside your boss. At large companies, office-wide softball games and charity 5Ks are quite common. Though these events are great ways to get to know the rest of the team, you don’t have to attend every single one. “Select the ones you enjoy most because you’ll have more fun and it will be easier to connect with others as a result,” says Schawbel. How will you get to know your boss at a charity bike-a-thon if you’re too fixated on the fact you haven’t been on a bicycle since you were four?

For an event like this, stay away from the professional conversation topics. While many people work out for health reasons, some hit the gym to de-stress. So why would you want to talk about work when you’re running or in that intense spinning class? When Kirsten Ballard, a rising senior at the University of North Carolina who interned at a newspaper last summer, ran several 5Ks with her managing editor and a fellow intern, she made sure to keep the conversation casual. “I’d ask questions about the local area, especially if there was something I was unfamiliar with,” says Kirsten. Try breaking the ice by asking your boss about restaurants and coffee shops you should try this summer.

Still on the fence about working out with your boss? Kirsten says she noticed a change in her office’s environment after her 5K. “After we hung out, the office became more relaxed and more fun,” she says. “I felt more comfortable joking with him in the office, and it also made it easier to ask for help or advice about tackling different projects.” Getting your exercise in and bonding with your boss? You’re basically killing two birds with one stone.

Regardless of the situation, the way you act after hanging out with your boss is just as important as the scenario itself. Though you may have bonded with your supervisor in a different environment, don’t forget that you are still his or her employee. So send an e-mail to let your boss know how much you appreciated the quality time, and show her that you’re still the superstar intern he or she hired.

*Name has been changed.

Photo Credits:
Kelsey is a senior at Boston University, studying Magazine Journalism  in the College of Communication. As a magazine junkie and fashion fanatic, she loves being a part of the Her Campus team! At BU, Kelsey is president of Ed2010 at Boston University.  She has interned for Time Out New York, Lucky, Anthropologie, and Marie Claire. Kelsey also has a fashion blog, The Trendologist, where she covers the latest trends, fashion shows, and red carpet reports. When she isn't busy, Kelsey loves hanging out with her friends and family, shopping, reading style blogs, going for a nice jog, listening to music, creating baked goods in the kitchen, watching movies, and eating tons of frozen yogurt and sushi! After graduation, Kelsey hopes to work as an editor for a fashion magazine. Follow Kelsey on Twitter and Instagram at @kmulvs and don't  forget to check out her "Catwalk to Campus" blog posts!
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