A few months ago Spreadshirt, a German design-your-own-T-shirt website, opened its U.S. headquarters here because its Boston-based CEO wanted to be in a creative-minded city filled with hip college kids and a deep techie talent pool. The site allows users to conceive their own shirts, set up virtual shops for their designs, and earn royalties by selling them. Since we at Boston fancy ourselves relatively on the pulse, we launched an office contest to see who could create the wittiest tee and move the most product.

So how did it go? Well, let’s just say Crystal Pepsi got off to a more promising start. We all appreciated the site’s vast selection of blank T-shirts from edgy American Apparel, and the challenge of coming up with the pithiest one-liner really got the neurons firing. Sadly, though, our impatient (and apparently less than tech-savvy) staffers were quickly discouraged by the site’s clunky design interface: We wasted time fiddling with Photoshop to get the images right, and some of us were forced to run to the art department for assistance.

Thus the contest descended from perk (Woo-hoo! Free T-shirts!) to chore, with most employees dropping out of the competition. If Spreadshirt ever gets better image-transfer capabilities and a 24-hour journalist-friendly help line, we might take another stab at a showdown. But until then, we’ll be forced to sport store-bought T-shirt wit.