I don't think he's judging your character or personality -- I think he's extrapolating from "I've never had a girlfriend" to "I haven't experienced much of life

I don't think he's judging your character or personality -- I think he's extrapolating from "I've never had a girlfriend" to "I haven't experienced much of life beyond work yet". If you've got enough money for ten years (or longer, as you say), why not take just a bit of it and travel for a while, or volunteer for a charity or something? You might just find something that does restore your sense of purpose.