After eight years of working a sole proprietor, I thought I had seen it all when it came to clients. You see: the road to new business is paved with potholes. There are complete strangers who think nothing of asking a freelancer for free advice (a.k.a. “Picking your brain”), former colleagues who see nothing wrong in asking for some free help (“It’s just a quick press release”), and current clients who expect a freelancer to be supportive when they suspend your contract for a month… or three… or forever.

The self-employed walk a constant balance beam of new business marketing, client service, and the need to earn a decent living. Nothing about working for someone else can prepare a freelancer for the ups and downs of working for yourself. But if you’ve ever gone on a date, you’re more prepared for freelancing than you realize.

Here are 5 ways that freelancing is like dating:

(1) Your online profile has been scoured already.

Web sites like LinkedIn or Twitter are the business equivalent to dating sites like Potential clients have already checked out your qualifications, your work experience, and maybe even critiqued your hair before they’ve typed that email or picked up the phone. Freelancers can find some comfort in the fact that 9 people have looked at your LinkedIn profile in the past 3 days, yet no one has contacted you in weeks.

(2) Courting can take days… or weeks.

Even after that initial email or phone call, the courting process can take days or weeks. It is the similar awkward dance of two people who are silently asking “I like you. Do you like me?” Someone has to make the first move….

(3) Your first meeting is for coffee… in broad daylight.

I remember my mother being very worried about me when I first started dating. She wanted to make sure that I wasn’t going on a first date with a serial axe murderer. Her advice: Meet him for coffee during the day in a public place. Guess what? The same holds true for a freelancer meeting her potential new client! (You may draw whatever conclusions you will about axe murderers and clients.)

(4) He says he’ll call… but will he?

Speaking of awkward dances, there’s nothing like the do-si-do that marks the beginning of a freelancer/client relationship; the shuffling of contracts, the review and approval process, the anticipation of starting on juicy new projects. But wait…. There’s a problem. There’s a delay in the contract approval process. “We’ll call you when this gets cleared up.”

(5) Breaking up is hard to do.

And like every new and wonderful relationship, sometimes a freelancer and client have come to the end of their time and must part ways. It begins with the “We need to talk” message and ends with uncomfortable conversations about getting your stuff back.