I've never successfully asked anyone out and, since the first (and last) time I did so, every relationship I've had had either happened by chance, or by someone else taking the initiative, or - perhaps - just assuming that this is the case now, and therefore...
It's different for people I've had sex with, although not massively so. In nearly all the cases here (barring one - Lilly - which actually half was, so I'll count that too), it was her making the initial move; my reaction was to just turn up and work hard on ensuring a mutually beneficial experience for us both, preferably involving one or more female orgasm. It worked... most of the time.
Like many people (but I won't be so presumptuous as to assume how many), I've also had my fair share of 'near misses'. There are those who don't appear or arrive but then leave, or even those who have come dangerously close but I haven't had the nerve. Some of my more reckless fantasies (which often replace myself with 'faceless male because I don't scrub up that well') focus on what would have happened had I actually had the nerve. Kiss that girl on the lips, rather than the cheek. Don't be so scared. Don't say you have a girlfriend when you genuinely don't. Tell her directly. Don't tell her at all. Ask for hugs and see. Just ask her for her damn number, how hard can that be?!
My mum (because she's my mum) was, and still is, absolutely adamant that, everywhere I spend a decent amount of time, there will be someone that fancies me. This includes the busy shop where I used to work, the church I used to go to, the university at which I studied, the school where she works, among the random girls I met in the park one Bonfire Night, Woodcraft, and the long-term job I recently had where the staff consisted entirely of married people and my 78-year-old boss. At each of them (the last one notwithstanding), I did indeed have my own crushes, but I was pretty sure that nobody there was at all interested in me, rather than having me as the somewhat peculiar friend who's good for a hug.
Certainly there wasn't anyone who wanted to have sex with me.
But it does, occasionally, get me wondering: what if I'm wrong? I certainly flirt with a lot of people, so what if I'm just misreading the signs of somebody flirting back and they genuinely want to tie me to their bed and ride me like a cowgirl on speed? Or even fall asleep spooning me because it's comforting, rather than worrying what society thinks or what would or wouldn't be right?
So I sometimes wonder what - or who - I've missed. Most of the people mentioned above have since gotten married and/or had kids and/or moved away. Or they've simply vanished into the ether like so many people I know do. And, with no way of knowing or changing past events or a "what-if?" spell, all I'm left with is a collection of tantalising possibilities floating somewhere around me in the ethereal plane.
Not that I complain... too much. I mean, it could have been worse... couldn't it?