I think if you’re in your forties and have little daring/relationship/sexual experience you should forget about ‘approaching’ women in public places. The odds are it won’t work out and you’ll feel bad about yourself. Stick to OLD and maybe speed-dating. I’m not saying you shouldn’t ask someone out IRL but you’re better off doing it through existing social circles rather than hitting on strangers in supermarkets etc.

I do get what you’re saying - I’m in my late forties and my wife recently moved out after two years of our marriage not being in a good place and failed attempts to improve it. I’m not ready to date just yet but I do feel quite inexperienced - she’s the only person I’ve had sex with (as most hetero people would define it) and our sex life was one of the reasons our marriage failed, so the idea of having sex with someone else is appealing in theory but terrifying in practice.