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.

FWIW, I never had a steady girlfriend till I was 23 (married to her and have a kid now, 6 years on) and it didn't bother me. Definitely don't feel pushed by society or embarrassment into prematurely settling down (or ever settling down at all, I know several people over 40 who have been permanently single and have rich lives).

Definitely agree here. A girlfriend is only one of many people with whom you can share a close relationship. Close non-intimate relationships with anyone can be just as rewarding.

I've done a lot of boneheaded things in my youth, and postponing romantic relationships to a later time probably would have resulted in me making better decisions when faced with the same situation. I'd like to think so, at least.