At what age do you start congratulating people on unexpected pregnancies? We're so used to congratulating people when we hear the news that they're pregnant. But, more often that not, the person was married and trying to conceive. If you're in high school and your best friend gets knocked up, you don't offer your congratulations do you? And yet, saying "sorry" sounds weird, too. But, if an older friend is dating someone and gets pregnant, what should the response be?