Four Reasons Why Freelance Writing is Like Dating

by Jodee Redmond

It occurred to me the other day that freelance writing is a lot like dating. Check out this list and see if you agree with me.

You Make an Effort to Make Yourself Attractive

When you are going out on a first date, you take extra care to make sure you look your best. The same thing applies when you are looking for freelance work. You send the prospective employer the latest version of your resume and you take care to submit samples that you feel showcase your best work.

You May Not Always Make a “Love Connection”

Sometimes you are really interested in seeing your date again and they don’t feel the same way. Sometimes it’s you that just doesn’t feel any magic.

You may be offered a freelance gig that once you find out more about just isn’t your cup of tea, and you decide to pass on it. And we are all familiar with a scenario where we just know that we are perfect for a particular job, but the employer doesn’t see it in the same way.

You May Get “Lone Rangered”

Picture a situation where you meet someone and everything just seems to fall into place. You share the same interests and goals and her or she is incredibly hot, besides. Everything is going great (so you think) until the other person magically disappears out of your life and you are left thinking “Who Was That….?” If this has ever happened to you, then you have just been Lone Rangered.

Freelancers have to deal the potential for getting stiffed by clients all the time. Thankfully, most of them wouldn’t behave in such an underhanded manner but it does happen that someone takes your work, sayts they love it, and then falls off the face of the Earth when it comes time to pay up.

You May End Up in a Long-Term Relationship

Everything might go well on your first date, and you may find that both of you are interested in seeing each other again. Over time, your relationships grows and develops until you are an important part of each other’s lives.

Sometimes, answering an ad looking for a freelancer may lead to your getting a steady flow of work from a client who not only loves what you do, but who pays on time. These are the kinds of relationships that many freelancers hope to find and that can work out beautifully for both parties.


  1. says


    This is one of the best articles I’ve read on the subject.

    In regards to making an effort to be attractive to someone, we may be trying too hard to give them what we think they want, rather than who we are.

    Of course, that’s not a wise mistake to make when dating since we’re talking about ending up in a potential life-long relationship, but it sure is hard when it comes to applying for writing gigs. I have both a professional side and a fun-loving side to my personality, and I’m learning that some sites want one and not the other, and it’s not always the professional side they are looking for in a “first impression” cover letter.

    Some sites want a writer to be free to be themselves, and others want a writer who can write what they want, regardless of whether or not it has anything to with who the writer is. That said, I’m glad freelancing gives the opportunity for me to write about only those topics that I enjoy-both fun and serious.

  2. Jodee says

    @ Phil: Good point/thought, LOL!

    @ Rhonda: Thank you for the kind words. Some clients want to get to know *you* and what you are all about, and some just want to pass out the work. Sometimes, you can make a connection just as a fluke. One of my clients gave me an assignment one time and for some reason, I acknowledged it by saying that I would “make it so.” Turns out she is a HUGE Captain Picard fan and she has now turned into my biggest-paying client. Maybe the comment helped, who knows? It certainly didn’t hurt anything.

    You’re probably better off being who you are in both situations. Either your date or the potential client is going to like what they see, or they won’t. Don’t take my word for it, though: I’ve been married for almost 20 years, so the only dates I am really familiar with right now are those things that look a lot like raisins! 😉

  3. says

    If freelance writing is like dating, than blogging is like being in a relationship. Why have only one if you can have two or three….

  4. Ann G. says

    @Jodee – I’ve been married for 17 years and we still go out on “dates” from time to time. Dating should never end! Most of the time, I’m in what I call “slob” clothes – like today capris and a tank top. Getting the chance to dress up and go out keeps me sane!


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