When you were working for Client X, communication was simple! You emailed them, they emailed you. They gave you assignments, you finished on deadline. The rules were clear.

Then you finished up your work with them, submitted your final invoice and wrote a “Thanks for everything” email. They, in turn, thanked you and said breezily, “Keep in touch!”

And now here you are, hunched over your keyboard, sweating neurotically. It’s like writing to an ex-boyfriend or ex-girlfriend that you want to reconnect with. How do you sound sane and friendly, while also expressing your interest?

Savvy freelancers know that the best clients are repeat clients and that it’s much easier to reconnect with a previous contact than it is to establish a completely new connection. But “keeping in touch” is easier to say than do.

How often should you check in with old clients? How do you touch base without sounding desperate? Well, here are a few tips for keeping those overtures breezy, relevant and productive.