You might. Just like people who divorce and get remarried probably have private thoughts like "well, at least she's not doing that" (whatever it was that drove you nuts the last time). But maybe being able to compare lends to some dissatisfaction with anyone who would become a permanent fixture in your life.
I think sometimes that I wish I could go back in time and tell myself things. Maybe not the three things I said I'd say the last time I blogged about Time Travel (but I'd probably say all those things and find a way to say more), but probably to say that really, I'm not the marrying kind. I think marriage is great for people who want to raise a family, but outside of that, there is no point. Especially if you want to have sex more than once a month (if you're lucky).
Or maybe that's the issue here - that I never got any action before marriage - thinking that marriage was the only "proper" context for sex, and also thinking that once married, I'd have all the sex I could handle. Not so. Maybe this is not the case for others; maybe mine is the weird situation, and everyone else is having sex "regularly", where "regular" means "frequent" and where "frequent" means twice to three times a week. I'm lucky if I get it once a month.
So what would I say to me in the past? Stop being a douche and ask her out. You want to bone her and she probably wants to jump you, so go ahead. And you're not incomplete if you never marry.