How Online Dating Prepares You for Freelancing

It was 12:42 in the morning, and I really needed to get some sleep, but I just couldn’t stop scrolling.

My eyes were blurring from reading descriptions that were either vague, or complete bullshit, but I kept looking, hoping even just one would sound good.

In disgust, I gave up, figuring I’d try again tomorrow.

This was me, in 2001, while online dating.

It was also me, in 2016, looking for freelance work.

I futzed around with online dating for about 8 months before hitting the jackpot (i.e. meeting my husband). And I’ve been futzing around on freelancing job sites for about the same amount of time, and have seen some pretty decent successes.

And I’ve realized that the lessons learned from both are identical.

Yes, one often involves a bit more nudity than the other. But both can do a real number on your self-esteem, your bank account, and your sanity.

So…now I know where the dregs of society hang out.

So, after learning a few lessons the hard way, I want to save you poor souls from having to go through the same agony.


Yes, I get it. You’re desperate for work and are seriously considering selling an organ. Or, you haven’t dated in so long, your naughty bits look like deserted-island Tom Hanks.

Oh, I’ve been there.

We’re gonna need a bigger razor.

When you start out freelancing, you’re so eager for any paying job, that you’ll accept any gig short of actual brain surgery. Or, with dating, any person short an actual brain.

This always, ALWAYS comes back to bite you in the ass, though. (And not in a fun, pervy way.)

Stretching your boundaries a bit and trying something (or someone) a bit outside of your comfort zone is good.

Leaping at something (or someone) completely incompatible?

Not so much.

What usually results is being tied to something that makes you miserable, while you waste a lot of time that could have been spent looking for a better fit.

If you MUST take on an ill-fitting situation (if you’re broke, or need a wedding date), don’t commit to anything long term. Keeping things short and well-defined keeps you from having an awful gig, or awful person, dragging you down for any longer than necessary.


“Do they like me? Will they call? Will I ever hear from them again?” You’re checking your email every 30 seconds like a caffeinated squirrel, waiting for a response.

But…hang on.

Do you even like them?

Whether freelancing or online dating, we tend to get so hung up on what kind of an impression we’re making, that we don’t stop and look at the impression they’re making.

Are they what you want? Do they make you smile? Are your philosophies compatible? Do they communicate well with you? And what DO you want, anyway?

It’s good to spend time thinking of how to wow someone, but you also have to take time to stop and ask if they’re wowing you.


Sometimes we’re so eager to make something work that we willfully ignore the blaring horns and flashing red lights saying, “Staaaahhhhp!”

You ask a potential client some questions to get a feel for their business, and they don’t actually answer any of them. Or, they ask you for a bunch of free “test” work. Or your online dating contact, who you’ve never met in person, asks to borrow money. Or they completely ignore the requirements on your profile.

If it feels dodgy, it is. ‘Nuff said. Get out.

You’re a snappy dresser, guy, but I said age 35–44, not 35 PLUS 44.


When I first started online dating, it was still a relatively new-ish thing, and not something that people would readily admit doing. So, I had nobody to ask for advice, or to guide me on how to separate the frogs from the princes.

But now, everybody from your best friend to your grandmother is swiping right. You can learn from their mistakes, or get their opinion on whether someone looks like a good fit for you.

Similarly, there are heaps of online communities out there for freelancers of all stripes. Join them. Now. Today. You’ll learn SO much faster from other freelancers with wisdom and experience than you will by muddling through everything alone. I’ve joined a few awesome copywriting groups on Facebook (hi guys!) and their advice has brought my business to a whole new level.

They’ve been through a lot.

Plus, if nothing else, it’s cathartic to be able to kvetch with other people who have been in your shoes.


I’ve seen this meme before and it rings true every time: “Don’t treat someone as a priority if they only treat you as an option.”

Or, to put it a bit more bluntly, if someone treats you like shit right from the start? Run. Because it’s NOT going to improve.

Now, will this advice prevent you from making any mistakes, in either online dating or freelancing? Of course not. You’ll make plenty of mistakes. And hopefully none of them will require a lawyer, or antibiotics (or both, in which case I MUST hear this story).

But if you can at least learn something from the mistakes you do make, you’ll be in a better position next time to get what will make you happy.

Just don’t forget to pass your hard-earned lessons on to the next newbie you meet. Trust me, they’ll appreciate it.