Help! I'm Dating a Client!

I don't know about you guys, but freelancing is an awful lot like online dating for me. For you married people out there or–worse yet–those of you who are happy being single, dating is this thing that you do when you meet a person and then you agree to talk to them over drinks. Then you decide whether you want to see them again or not (which is usually with a frequency of next to never) and then you go home and eat a pint of Ben & Jerry's and contemplate life plans that involve paying extra for rent.

So how exactly is freelancing like online dating? Well, for starters, there's a lot of people out there who claim to be looking for someone who's exactly like you (tall, handsome, charges a reasonable rate) but in fact are interested in something completely different (like your best friend). I can't tell you the countless jobs I've pursued with clients recently who seem totally into me only to find out later that they were just making polite conversation while getting someone else's number. Maybe humor's a hard niche to crack, but I've had the same experience trying to land even a normal gig of writing terrible product descriptions.

Still, I've successfully bid on a number of gigs, put out a quick article, and had a pretty overwrought response. It's scary to have a client get attached to you so quickly. I'm used to having to work for it a little.

"WE LOVE YOU!" they'll say, a bit too soon. I've only written them one article! How could they love me already? I get anxious. I'm still a man, after all. Even a whiff of the possibility of commitment causes me to run as quickly as possible in the other direction. Maybe female freelance writers have a different take on it. Maybe the promise of a commitment seems encouraging to you. Maybe it means that you go out and start looking at duvets together at Crate & Barrel. Me, I hightail it to the nearest sports bar and drink cosmos.

Sorry, but I'm not that good with beer.

Then after awhile, I start to pull away. I miss a couple deadlines to test if they really like me. I get anxious when they don't return my emails or my invoices. I know I've screwed up a good thing because I'm afraid to settle down, and then I have to go outside my client's webpage, blasting an MP3 of "In Your Eyes" by Peter Gabriel to show that I'm really the one that they want. Of course, life isn't a romantic teen drama, so they have already moved on to a humor writer who's maybe not as funny, but at least more reliable than I was. I find out later that they have a blog together, which sucks because I've always wanted to have blogs.

And then I go home to eat more Ben & Jerry's. My recommendation is Creme Brulée because it really tastes similar to the actual dessert. It also helps you wallow in depression better, which I do after I have my heart broken. But soon, of course, I'm back out there again, bidding for new gigs with a fresh perspective and then I find it: the perfect job. We have so much in common and when we don't, our interests are complementary. She's looking to spend, I'm looking to take her money. And then I start to work for her, put out one great article and then...

"We love you!"

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Clint Osterholz is a freelance writer who thinks he's awfully funny, and is surprisingly not a disappointment to his parents. You're always free to check out his portfolio if you'd like someone to be funny, or maybe write something a little more serious. Subscribe to my posts (only posts from this author).

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7 thoughts on “Help! I'm Dating a Client!”

  1. Have you tried playing hard to get or being brutal to the clients? People respond well to bad boys, you know. Maybe you should spew hate-filled vomit all over the internet and then the clients will be lining up to be abused by you – of course they will never leave you alone again, but it’s a small price to pay for being a total player. You know, I even have a website I can show you that will tell you exactly how to become a great pick-up artist. I think there’s even a free trial. *grins*

  2. Hilarious! I loved it!

    One thing I didn’t get though. Why don’t want want repeat clients? Wouldn’t that benefit your business, so you don’t have to keep looking for work? I understand the occasional client can get tiring, but, after reading the article, it seems to me like you do this with all of your clients. If not, please correct me. I’m just a little confused.



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