Five Things to Know Before Dating an Artist


A Piece by featured writer and good buddy of mine, Sam Weil

Congrats, you did it! You finally broke up with your college sweetheart and moved to the big city.

And no offense to her/him, but there was always something “off” with that one. And no, you’re not “crazy” for suggesting they were too clingy. It’s a common side effect of several years of stunted emotional growth. But anyways, that’s all in the past, now’s the time to live it up! Long days, longer nights. Enjoy the chase! Enjoy the dates!

Dating in the city is a whirlwind. I went through the aforementioned breakup-with-college-girlfriend thing, and let me tell you, I was blown away with the amount of opportunity to meet women. And not just any women, I’m talking a nearly different species of human being (Disclaimer: I grew up in suburbia-hell Connecticut so let’s just say dating diversification was “limited”). Actresses, dancers, photographers, writers, fighters (not kidding), and so many more types of artists.

At first it was overwhelming, especially transitioning from such a low-energy environment. I might’ve enjoyed more success had I known a few key things. Artists are a tricky bunch. Alluring, mysterious, but a fucking maze to navigate. If you’re navigating the maze for the first time, here are five things to keep in mind.

1. Ditch the Elevator Pitch

Artists are not corporate soldiers. Where are you from? Where do you see yourself in five years? What are your best skills? Although valid questions, they’re not going to keep his/her attention, and they definitely don’t give a shit how you would respond. Their attention has already turned to something more interesting.

Instead, try and speak with spontaneity. What does that mean? Well, don’t sound rehearsed. Tell engaging stories, ask random questions, remain somewhat mysterious and leave her wanting more. This isn’t a job interview – you don’t have to sell yourself in 20 minutes! Develop a quippy rapport and prove you’re not just another white collared cunt.

2. Don’t Default

You know when you buy a new toy and choose the default settings because you’re too lazy to customize it? Default date setting prime example: Drinks after work, tapas after that, maybe a rooftop to seal the deal. Hopefully you get my point, and honestly, the only thing you’ll seal is the inevitable fate of no text back!

Be creative, man! Actually put some thought into this. Artists crave inspiration so show them something they’ve never seen before. Maybe there’s a small garden or view-point you only know about. Perhaps there’s a public performance or live music waiting to be stumbled upon. Either way, the city is never short of options, so get the creative juices flowing and steer clear of the standard drinks-food-more drinks routine.

3. Expect the Emotional Unexpected

I hate making assumptions and so should you. When dating an artist, never guess his/her emotional state, period. The same can be said for pretty much anybody, but its importance is paramount with artists. From what I’ve experienced, most artists don’t choose their career path lightly. Often a life experience inspired them to pursue the road less traveled, and it’s also possible this experience left them emotionally volatile. Not always, but often.

My advice – don’t prod at their past and instead let them open up to you at their own pace. And if you experience any emotional volatility (like a random argument because no, you don’t think the painting represents early Vietnamese feminism (true story)) keep your cool and hopefully she apologizes and explains herself later on. And if not, well, there’s always the prospect of angry artist sex!

4. Stay in Your Zone

You don’t know Monet. You definitely don’t know ballet. And if you think for one second you can hold your own with Opera, then you’re a bigger fraud than Shkreli. So, don’t try it! We all talk out of our asses. There’s no shame in trying to sound smarter than you really are. But again, this isn’t a job interview, and artists will figure you out before you finish your first drink.

Simple solution – listen and learn! Take a genuine interest in what they have to say about their craft. Ask specific questions. Chime in when appropriate but let them hold the reigns. Yes, it can be intimidating to know nothing in front of an expert, but relax big guy, she already took the date! You’re halfway home. And if you happen to be good at something outside of work, sports and binge drinking, then flex your intellectual and creative muscles when the opportunity presents itself.

5. Leave Sensitivity at the Door

Imagine taking a constant barrage of criticism over your body, talents, and ability to inspire others day-in and day-out at work. Imagine struggling to compete with hundreds of equally talented peers just to secure a couple weeks of income (and in many cases, simply to put something on your resume). Shit, imagine having the mainstream look at you as a feeble-minded imbecile because you choose to do something that most, frankly, don’t.

What’s my point? Well, this is what artists endure. Their careers are hyper competitive and rarely succeed; there’s no time to feel sorry for themselves. Sometimes, this spawns a sort of cold-blooded personality that doesn’t feel bad for the tough situations of others. I’m not suggesting they’re mean-spirited bitches, but I am saying it’s likely they don’t offer condolences because you had to take an 8am conference call or you scuffed your new pair of Ferragamo shoes. Seriously though, don’t expect an artist to be sensitive to your every need and situation. They have their own shit to go through. If you need someone to pat your back and assure you that everything will be alright, an artist may not be the one for you.


**So next time you’re thinking about dating an artist, remember my friends tips: Don’t be Captain Corporate America, Be Spontaneous, Stay in Your Lane, Don’t Be a D*** and above all else

#DateTirelessly Screen Shot 2017-09-21 at 12.38.37 AM



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