4 unexpected realities of dating a freelancer

Feb 9, 2016

Ah, Valentine’s Day! The perfect time to celebrate the gruesome martyrdom of two different saints… er, I mean, romantic love.

Since this is the Freelancers Union, I thought I would extol the many virtues of dating a freelancer!

As part of a two-freelancer household myself, I both receive and inflict, er, uh… exercise my freelance lifestyle on my loved one. What a lucky duck he is, huh?

From my love life to yours, I present: The Four Realities of Dating a Freelancer.

1. Free time

Sometimes, your freelancer will have seemingly endless availability! Like on select weekday mornings, when you are dragging yourself out of the warm bed to do a 2-hour commute. At this time, you will debate winging a shoe at your blissfully snoring freelancer. Do not do this. It hurts us.

On the upside, we are totally available to come meet you for an impromptu lunch. You eat lunch at 5 PM, right?

2. No free time

In recompense for all of the aforementioned flexibility, your freelancer may occasionally turn into a hollow-eyed, shambling maniac, keeping you up until 2 AM with frantic tapping on computer keys and muttering. The only word you will be able to make out is DEADLINE.

You will see us in one week. Like goldfish, we will have no memory of our past behavior. We were totally on top of that project, what are you talking about?

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3. Feast-or-famine mentality

Your freelancer may, from time to time, evince all the qualities of a needy golden retriever. That is to say, we will be excited to see you when you finally get home – we were so LONELY for COMPANY we want to PLAY – and very cognizant of the mailman’s arrival.

Was that the mail? Did you get the mail? Did you see an envelope for me? Did it look like a check? Hey, are you sure?

Before the check comes, there may be strictly-enforced ration times. Dates will consist of an evening with ramen noodles and Netflix – everything but blackout curtains.

Your freelancer is likely to take to wearing tattered sweaters (they haven’t done laundry since before the Hard Days Came) and delivering bitter invectives about the U.S. Postal Service, their clients, the nature of time itself.


4. Realities of the self-confidence spectrum

Your freelancer is completely confident in himself/herself! After all, she/he is playing outside the rules, remaking the game, blazing their own path – and there’s never any doubt involved!

Except when we submitted that project and there was no response for a week. Wait, now it’s a week and a half. Probably everything’s fine, right? We called and there was no answer. Probably they liked it, though, and their voicemail is just turned off. Probably. Probably they didn’t hate it. Probably we’re not summarily fired.

Probably the business didn’t completely go under and their furniture is being carted away by Repossessions-R-Us as we speak and the check will never come and oh God we won’t be able to pay the rent and we’ll never get any clients again and we’ll be tossed in the street and forced to put on puppet shows in cardboard boxes for spare change and eat alley rats (our only friends) for dinner but even then you won’t leave us, will you, baby?

… Baby?


Oh, the client called? Oh. The check is in the mail?


Happy Gruesome Martyrdom day, all!

Kate Shea lives and works in New York City, where she consumes an inordinate amount of Sriracha daily. You can catch up with her on Twitter at @katerone.

Kate Shea

Kate Shea lives and works in New York City, where she consumes an inordinate amount of Sriracha daily.