To answer your later questions, I'd have to say making plans with friends and hanging out with my dog and two cats are how I handle the holidays, Valentine's day, etc. I've spent depressing, bummer holidays alone in the past and basically learned that I had to anticipate and make plans so that I'm not alone and super-lonely. While I can't say I "hate" being single, I also become painfully aware of it sometimes but have learned that I don't have to isolate and be bummed (hanging out with my own bummed-out self has never proven to enhance the loneliness!); I can make plans with friends or babysit or invite other single friends over, etc.
I didn't answer the strategy question. I think I would join a Church singles group and maybe a book club where we take turns hosting meetings. Maybe even something like Toastmasters...
I actually didn't think to ask about strategies for dealing with the holidays as a single person without a current prospect, but the question is worthwhile. Your answer is good as well.
I've not had much luck making big plans, and I've often had better success going the other direction. I tell myself that the day isn't going to be special; I'm going to hurt a little bit because I'm spending the day alone; I can't expect to make the most of that day of my life. Lowering my expectations this way sometimes makes me better prepared for whatever I encounter, and if I'm prepared, I can sometimes still find something worthwhile. Even if I do little more than take a walk and watch a few hours of a "Law and Order Marathon," I've done better than if I'd just sat in bed staring at the four walls.
Bill