Just a lil'bit more info...the only rule I know (and use) is not to mix font categories. Unfortunately, the only categories I really know are the broadest three: sans, serif and script (don't mean to insult or irritate anyone if I'm not correct).

Although I'll never get caught using Papyrus again, for illustrative purposes would anyone be willing to explain to me the qualities you'd observe about the font in choosing a complement for it? What questions about the known font should I ask myself in order to create a pair? I can't even categorize a font like Papyrus so that means the only rule I know is ineffective to me in that instance.

Thanks everyone in advance for your thoughtful responses!!!

It's not really a matter of having an "eye" for it. If it were, there would be no pointers anyone could offer seeming as how you don't have the "eye".

If you just want a basic understanding I would say it's simply a technical matter, and you don't need to invest tonnes of time to have a fundamental understanding of how different types contrast. The two most helpful starting books for me were Design With Type by Carl Dair and The Elements of Typographic Style by Robert Bringhurst. Either is a great read and good to have around as a reference if you plan to do work with type.

This newsletter from Hoefler & Frere-Jones (prominent type designers) does a nice job of explaining some combinations for (their) typefaces.

This listing shows various Typophile posts on pairing fonts.

What do you mean exactly about not mixing categories? Surely, using a sans font for display/larger text and a serif for text/smaller text is a fairly traditional method of pairing.

The qualities to observe can vary. For example, say you want to use Helvetica. Simply relying on boldness/weight to provide contrast can allow you to use a regular version and a bold version of the same typeface. They complement each other because they share the same shapes/forms/style but differ in the thickness/weight.

On the topic of Papyrus, I would classify it as a distressed (roughened/textured) script. Something can be a script without looking like cursive; Papyrus is closer to calligraphy. You needn't swear off Papyrus forever, because I'm guessing you don't have any other fonts like it (if interested, this is a helpful list). Just know that Papyrus is very widespread in its use. Many designers consider it amateurish due to its misuse and overuse.

If you truly want to develop a greater sense for these things, I encourage you to read Typophile regularly. I have found it invaluable. Also, experiment and practice can only help.

Apologies for the long response.

My understanding is that one rule of thumb is not to combine two faces in the same category.

Thus, mixing Franklin Gothic and Times Roman is not so bad, because there is a strong contrast between them, one a bold sans-serif, and one a normal serif, but mixing faces that are similar (yet definitely different, and thus not matching), such as Caslon and Times Roman is what one isn't supposed to do.

I'm fairly sure that this has been given as a rule of thumb to beginning typographers in a number of textbooks on the subject.

http://typophile.com/node/32056

Perhaps you might email your friend and just ask her? (since you seem to have been happy with previous results of your collaboration)

I'm at least glad that when I followed the link given, I found a link in that discussion to Typeface Pairing which gave a link to

http://typophile.com/node/45613

which shows that I was not imagining things when I said that a strong contrast is the "safe, boring" recommendation.

However, you don't need to use a sans-serif for titles if you are intending to use a different face from the serif type used for body copy. An Egyptian will do. A Clarendon will do. Even the contrast between Bodoni for headings and a serif Roman which is not a modern will do. (Although, to be safe, one likely will use a bold weight for the headings for a little extra contrast.)

However, while contrast is good, another one of the safe rules of thumb, I saw from that thread, is not to combine two faces with a strong personality. So one doesn't use two display faces at once. No mixing Papyrus with Hobo, or Cooper Black with Comic Sans, or even Amelia with Albertus.