Ha ha...T-shirts...that reminds me of something funny. My sister dated a real loser of a guy for almost 3 years...he was OK at first, but as they "grew up" he "grew" into an idiot. We finally knew she had moved on when she appeared wearing 2 hilarious shirts: One just said "Have you dumped your boyfriend today?" on the front. The other one said, "I'm not with stupid anymore," and she had his old football number screen printed on the back of it.
Maybe you could get one of these and he would take the hint to straiten his act out?