Should your social media really show how much you like to party?

Welcome to HTTP’s and Q’s, where we’ll be answering your most pressing Internet etiquette questions—Internet-iquette, if you will. Have a Web-based moral dilemma that plagues you each time you unlock your home screen? Send your problem to [email protected], and it might be answered in the future.

Question: I want my Instagram to show that I like to have fun, but I also don’t want people to think I’m a total mess. How do I toe the line?

“I’m a mess but I make it look so good,” Kyra LeMoyne Kennedy’s Instagram bio once read. That is, before her famous father, Robert F. Kennedy, Jr., had a talking-to with his 20-year-old daughter.

Kyra was reportedly told to “clean up her Instagram,” according to a Page Six source, because her father did not like the way she was representing their family’s American dynasty by flaunting her lavish lifestyle. Later, it was reported that the incident even lead to her being forced to spend this past summer with the Kennedy family in Cape Cod and Florida to get it together. (Oh, the horror.)

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A photo posted by Ms. Kyra LeMoyne Kennedy (@mskyrakennedy) on

If Kyra Kennedy’s situation teaches us anything, it’s that even the moneyed and powerful are image-conscious and need to think about the type of lifestyle and moral fiber that they’re presenting to the world via the Internet. The question is: What is the right amount of debauchery? And is there such a thing?

First, let us look at one extreme end of the spectrum. If you want to see butts, boobs, a shiny glock, or two girls making out on any given day, you can head over to Dan Bilzerian’s Instagram, where the billionaire often shares stills of his life that can only be described as debaucherous. You can tell he’s proud to be the social network’s playboy king, and inspires others to follow suit. Same, too, with  Tony Toutouni, the Iranian billionaire whose photos show him literally giving the middle finger to everything.

For regular people, though, how you present yourself to the world over social media can be something of a balancing act.  You want your Instagram and Facebook friends to know last night was fun…

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….but they don’t necessarily need to know how the fun got started.

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“I think like attracts like,” Anthony Recenello, a dating coach in New York City, recently told me over coffee. Recenello, 31, is of the mind that you’re better off putting your truest self out there, rather than a canned version that doesn’t accurately convey who you are and what you’re looking for. This means being completely honest about yourself on your social media. “I actually think it’s better to let your freak flag fly,” he said.

From Recenello’s perspective, the only thing you really need to worry about is how your crazy party photos might affect business relationships and potential employers. If your settings are private and only personal connections can see your Instagram, Facebook, etc., then have at it. 

But this is where we differ. Speaking from personal experience, I know that the second I see “Work hard, play hard” on a guy’s Tinder bio, I immediately swipe left. Same goes for a photo that appears to be at a club with three shirt buttons undone, surrounded by bros and a clear drink in hand. There very well may be people who truly work as hard as they play, party all night and get up before sunrise to do community service. Alas, when someone shares what looks like a party-hearty lifestyle with little context, it’s easy for others to draw certain assumptions.

The old standby of Would I be embarrassed if my parents saw this? is no longer a good enough benchmark for the type of content you share, seeing as most of us put out so much garbage on the web these days that our parents’ embarrassment wouldn’t even know where to begin. Perhaps a better question to ask yourself is If I look back on this photo is 10 years, will I want to go back in time and strangle my younger self?

But Recenello thinks social media is all in good fun and that the images you share naturally reflect the process of maturing and the type of relationship you’re looking for. “The biggest thing you need to ask yourself,” he explained, “Is ‘What do I want to present to the type of girls or the type of men that I’m interesting in?’ And go from there.”

For many of us, the images we share on Instagram and Facebook are meant present a curated versions of our lives: Your most beautiful food photos, the most stunning landscapes you’ve laid eyes on, the camera catching you and your friends at your best angle. But if you’re happy to be seen as a devil-may-care partygoer, then you do you. Just don’t be surprised when your date sits down and immediately orders a shot of tequila.

Photo via Mack Sennet (PD) | Remix by Jason Reed

Marisa Kabas

Marisa Kabas

Marisa Kabas is a lifestyle reporter and activist. Her work has been published by Fusion, Fast Company, and Today. She’s also served as an editorial campaigns director for Purpose PBC, a social movement incubator.