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iPhoto’s Smart Albums are great when you want to find a subset of your photos based on certain matches—all images newer than last week, for instance. But what if you want to do something more complex, like finding pictures of your cousins Bill and Will? Here’s an undocumented trick to add some degree of flexibility: If you’re using iPhoto 5, you can employ a number of wildcard characters when building Smart Albums based on the “Any Text” criteria. (You need to have given your photos descriptive names, applied Keywords, or typed comments in the Information field for this to work.)

iPhoto 5 supports these wildcard characters: the asterisk ( * ), which stands for “any number of characters, including none”; the question mark ( ? ), which stands for “any one character”; and square brackets ( [ ] ), which are used to select from a list of characters, or to just quote the actual asterisk and question mark, in case you wish to actually search on those characters.

In each of these examples, the starting point is a new Smart Album (File: New Smart Album) with the criteria “Any Text” and “Starts With.” Now consider the following possible contents for the actual search string:

  • T?m: Match all photos that contain the string Tim or Tom , but not Them (since there are only three characters in our search string).
  • B*e: Match any photos that contain a string that starts with a B and ends with an e. So you’d see matches for Base and Bike and Brittle and even Be . You would not, however, see matches for Brighten , since that’s got an extra character at the end.
  • B??t: Finds Boat and Belt but not Burnt (since that’s got three characters in the middle, and we’ve only allowed for two).
  • Mari[ao]n: Finds only those images whose text matches Marian or Marion .
  • C*r*: You’ll get lots of matches here, as it’s basically saying “find any text that start with a C, has any number of following characters, then an r, and then any number of additional characters (including zero).” As such, Car , Cars , Characterization , and Chart are all examples of words that would match.
  • Finally, what if you want to match an actual * or ? character? Just enclose the special character in square brackets, like this: Kellie[?]. This search would only match images that were marked with the text Kellie? — perhaps you’ve got some people you haven’t quite yet identified in your images :).

Note that these wildcard characters will probably prove most helpful in the middle of your search terms—iPhoto already does a kind of “any match” search for longer matches in your library. For instance, a search on “Tim” will also find pictures labeled “Timmy,” which is the same result you’d get with a “Tim*” search. How does this work in practice? Below is a square-bracketed example for finding all images that contain “Tim” or “Tom”:

When you add wildcards to iPhoto’s Smart Albums, you can find almost any subset of images. Given the similarities between iPhoto and iTunes, you’d think this same thing would work in iTunes…sadly, at least as of today, you’d be incorrect. For now, this is an iPhoto-only trick.

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