Whenever my brother, Alex (a different one than the one mentioned in the post about Rice), and I are in New York at the same time, we always end up going out with his friends from college. Growing up, I always wanted to tag along on what my brother was doing, and he was usually pretty great about having me around, if you disregard a couple of years during his mid-teens when he needed space.
Luckily, as a grown-up, he's no different and loves to have me come along. Alex's friends are always a blast to go out with because they know how to do it right; there's never any chance that we'll end up sitting around at the end of the night regretting that we put the effort and money into the ordeal.