My boyfriend got me a T-shirt that says talk nerdy to me. I just love it, and it gets me lots of attention. Not sure how much of that attention is because the lettering is over my boobs… but it’s all good.
I’ve wanted to get a shirt written in Chinese that, translated, says something to the effect “Another dumb American got a T-Shirt he can’t read.” Would only be funny to someone who could read Chinese, though.
This is not really on topic, but I wanted to mention the polo shirts my boss had made for us a year or so ago. He had to give our periodic Security Talk, and he want to remind us we were all potential targets.
So he went with a red 30cm target on the back, a smaller one on the breast. They are a big hit. (Although I never wear mine off the compound.)
We expats are weird. Way weird.
The best I’ve seen recently was a black T-shirt with the flag of the United Kingdom on the front. Underneath the flag, in blod letters, it reads GREECE.
My wife wears one that says, “I [heart] Skinny Boys with Glasses.”
Which, not coincidentally, describes her husband pretty well.
I always wanted a t-shirt that said, “Celebrate the Ides of March, stab a friend today”
you can get that one yourself right here (lots of other good ideas at that site BTW)
AL FRANKEN
FOR PRESIDENT
Oh, get this one:
http://www.randomshirts.com/productinfo/clearance/mariachimisprint.htm
They also sell the correctly spelled version, if you prefer that.
Raskolnikov did it.
My two favorites:
“Please tell your boobs to quit staring at my eyes.”
and
“50,000 battered women in the world and all this time I’ve been eating mine plain.”
yes, I am pimping my store. But dammit, when I wear this T-shirt in public, it demonstrates my intellectual mastery of all things, and makes attractive women want to sleep with me. If you want to pick up a hot doper chick, try this one.
I like this one. 
I’d probably talk to a guy wearing it.
Or wear it myself. 
A while ago, there was a thread that included pictures of dopers for some reason, and one was pictured wearing a red shirt with white lettering on it that said
“Global domination goes better with a Coca-Cola”
The Coca-Cola was in the traditional script. I have wanted that shirt ever since I saw it (It would go well with my Nike hat embroidered with “Capitalist Oppression”). You should make one of those. Well, two, and send me one.
Plain text I’ve seen on shirts worn by cool people I know:
Listen to Bob Marley.
Fuck Idaho.
I’ve always wanted to make some guaranteed-to-get-my-ass-kicked-by-a-drunk-redneck-with-no-sense-of-humor t-shirts:
“I’m Molesting My Inner Child”
“I’m Fondling My Feminine Side”
I want to point out that women who will sleep with you because of what your t-shirt says are not worth sleeping with.
However, a clever t-shirt can be an icebreaker. Just don’t expect it to work miracles. You’ve got to have a personality. Or lots and lots of money.
I have a cafepress store with a few shirst. One of them had a silhouette of a zombie with a red circle and line through it near where the breast pocket would go, if it had one. Underneath that, it says “God I hate zombies.”
The back has a picture of people shooting at a zombie, and says “Anti-Zombie Patrol…Taking them out, one at a time.”
I also hve one that is a picture of the 8-bit sprite of Link from the first Legne of Zelda. Underneath it says “8-bit Hero.”
I also have one that is a plain white t-shirt and in a handwriting-esque font, says “I Hate Bottles.” I’ve sold more of those than any other, despite the fact that it’s the most obscure.
Or be his friend with:
“You plug it, you punge it.”