Loren Brichter of Tweetie fame released Letterpress yesterday, an incredibly fun and addictive multiplayer (Game Center) word game. You form words from a 5×5 set of tiles while stealing tiles from your opponent with a goal of having the most colored tiles when the game ends.
As with most fun games, the rules are simple but mastering the game is hard. The two most important ingredients to winning at Letterpress are a basic strategy and a large vocabulary. The former I’ve laid out below and the latter, well, there’s always a little help available if you need it.
Basic strategy
Since you’re chasing points (i.e. tiles in your color), your apparent goal is to get as many points per turn as possible. But actually it’s not the absolute number of points that matters. All you need to win is one point more than your opponent. So your real goal isn’t just to get as many points as possible, it’s also to steal points from your opponent.
The first order of the day is to use your opponent’s light-colored (non-defended) tiles to build your words, if possible. That way you gain a point for each letter used while also stealing a point from your opponent. You’re basically getting two points for one.
The second part of the strategy is for finishing the game: If you’re ahead and there are only a couple of white (uncolored) tiles left, try to form your words with these letters to end the game. If, on the other hand, you’re behind, keep on forming words from your opponent’s light-colored letters as long as possible until you get the upper hand. Then go in for the kill with the white tiles.
Always play plurals
If you can, always play the plural of a word. If you don’t, your opponent can just take your singular word and score with the plural. But the rules don’t allow the other way around, so by playing the plural you’re blocking both forms of the word for your opponent.
The same goes for adjectives: If you can play dirty, don’t just play dirt.
Bonus: Defend vowels
If you want to make it extra hard for your opponent, try defending vowels. There are usually only very few vowels in the game and you and your opponent need each one of them to form words. Since your opponent will try stealing your tiles, if he steals your defended vowel tiles, at least he won’t get credit for them because defended tiles score zero points. So while he may be able to form words, he’ll have a harder time gaining critical points.
Vocabulary
The best strategy won’t do you much good if your vocabulary is too small. Fortunately, we have the Internets to help us out. Your goal, as per the basic strategy above, is to form your words by stealing your opponent’s tiles. But it’s not always easy to form words from those letters. Fortunately, there are tools available that can help us improve our vocabulary.
The most useful tool I found is from Litscape.com. It returns words that contain only the letters you enter. So all you have to do is enter all the letters on your opponent’s light-colored tiles into the form and then pick the longest word from the list the tool returns. It’s no guarantee for success, but I bet you’ll find many words you wouldn’t have come up with on your own, all the while making life for your opponent significantly more difficult.
Conclusion
Keep in mind that the whole point of games is to have fun. Winning is usually more fun than loosing, but playing the game should be fun no matter the outcome, and chasing the leaderboards shouldn’t be your foremost motivation. Whether you use these tips or not, Letterpress is great fun. So if you feel that using the aforementioned tool is cheating, don’t use it. I, for one, think it’s a great way to learn new words. And if I’m making it harder for my opponents to win against me, maybe I’ll motivate them to expand their vocabularies too 
Update: Here’s someone who has apparently built himself a little app to, *cough*, optimize his game:
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