There are two occasions when it is very difficult to be cool and an older single guy. The first is Saturday after about 10:30 in the morning, and the second is on any kind of away-from-home holiday.
Saturday is couples day, parading-our-domestic-bliss (or misery) day, groups of people having fun day, football day, let's go running in the park with two hundred other people day. Saturday is the one day when it isn't grown-up and sophisticated to be doing something on your own. An early breakfast on your own is just about okay, but after that the Couples take over, bringing their entitlement and crying babies with them. (I live in London, your Couples may be nicer.) Saturday night is, of course, amateur night out. A sensible older guy gets an early night so he's fresh and ready for the gym Sunday morning.
Away-from-home holidays are weird when you're an older single guy. Especially if you have, as I have, forsworn mood-altering substances. It's one thing to spend the day in a slight alcoholic daze, and another entirely to be awake at 06:30 with sixteen hours to fill before bedtime - on your own. No-one to talk to, no-one to shag, no-one to eat with. £1,000 for airfare, hotel, food, car rental and gas: that's expensive sand between your toes. A thought that will vanish the moment you hook up and actually get laid. Which is why the "older guy" bit matters. Older guys don't hook up on holiday. (Very few people hook up on holiday - except drunk English women with local guys.) A holiday is a strain of its own that only single guys know about ("I'm enjoying this, I really am, this is interesting, it really is, look at that, look at this" is a mantra that goes through your head a lot).
On Saturday morning, and the morning of any away-from-home holiday I want to wake up in a good hotel in Paris, Amsterdam, New York, London, or a beautiful beach location, with a sexy woman next to me, make love again, have breakfast in bed, watch her shower, and walk round wherever like we own it, which with her beauty and my whatever it is that I must have for her to be there, we will.
That's not going to happen. I don't have the money. For the airfare and hotel, let alone the woman. However much I know all this stuff, Saturdays and holidays always get me down. ("Rainy days and Mondays" have nothing on "Saturdays and Holidays"). Perhaps "down" is too strong a word. I can't escape the hollow feeling. Which vanishes the moment I wake up Sunday morning. (If you're single and a guy and not in a relationship, yes, there will come a time when waking up alone Sunday morning will not hurt like a mofo. Mind you, not for a couple of decades.)
Which is why I have years when I don't "go on holiday" and years when I do. And why Saturday never feels right, no matter what I do. The reason I know this about being single and the timing, is that none of this happens when I stay with friends at weekends, and none of it happens during a work-week. Saturday Bloody Saturday.