Hi everyone,
What’s the most gracious and tactful way of asking someone who is a friend to be paid for a freelance job that is overdue?
Thanks. 
Hey, You owe me money!
Doing work for friends is one of the fastest ways to ruin a friendship.
Up front you have to be clear, even to the point of using your standard business contract.
First of all don’t involve your friends or relatives in your professional life.
Now you should start talking about your design and its costs indirectly, if he is mature enough, he’ll get your point!
Exactly!
On the up side, you don’t lose a friend … you just rid yourself a freeloader. It’s worth it.
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Send them an invoice.
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Business is strictly business. Usually my friends are pretty good but doing work for family…ehhhhhhhhh
Language warning.
I guess the problem lies in why your friend doesn’t think he needs to pay you.
I mean, if he’s picking up your beer tab every night, maybe he doesn’t think he owes you anything.
And I guess the other part of it is, is it enough money that you’re willing to risk that friendship?
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Seriously? Maybe the “friend” thinks it’s friendship, but the OP thinks is suckership.
Call the friend under the guise of quality assurance… tell them you like to follow up on your projects to see if it met their needs and how it was received by their clients. How was the process, did it meet their expectations, etc. Discuss that first, then bring up the past due invoice. If they say they are having a difficult time paying, offer an installment plan. Also, it can help if you are able to accept credits cards. Then you can get the full amount you are due, and they can pay off the credit card company over time. Or if you are feeling generous, offer to bill them in installments on their credit card. Then they could really stretch it out over time without taking too much of a hit on interest.
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I wouldn’t use any guise. Just send an email or call with an honest ‘gentle nudge’ on the overdue invoice. If this person is a friend, they won’t need to have it sugar-coated.
To my mind, if they take umbrage, then I would be questioning the quality of that friendship. If they continue to delay in paying up, then it goes beyond simply questioning.
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You may need them someday 
Good point. He already paid me for the first job. I guess I feel a bit funny asking for money. I’ll remind him this week.
Excellent advice! Thank you.
Update: My friend did pay me. He also said he will have more work for me, but he’s so busy he can’t get to it right now. I’m not sure if that’s his polite way of brushing me off because he was not happy with my work, or if it’s the truth, because I have yet to get more work. Either way, life goes on.
Eh, for sanity’s sake just assume he’s busy. But follow up later. Clients will do this to you all the time because they really are busy. It often pays off to follow up later. 
Never charge a friend or member(s) of family. They’ll end up owning you.
Huh?
I’d charge em double, myself if I could, cuz you gotta put up with them after. Clients go away.
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That’s a good manouvour. The pay-off is two-fold. One, you make double. Two, chances are, it’s just the one time. Win.
That is, if they pay.