I count myself lucky that my wife has been very enthusiastic about sailing, so most of the time we're out together, and so far, it's been a very good thing. However my weather tolerance is still wider than hers, so on occasion I'm out with a buddy. I still haven't single-handed this boat much, but at 19' I have no excuse for not singlehanding her whenever the mood strikes, and I may just do so next year, work (or lack of work) permitting.
We enjoy belonging to a yacht club, and we are also part of a very active class association that holds some great outings every year.