His mentality about it and anxiety about the age are going be what fucks it up if anything. It's not like it's hard to fuck. Maybe lasting is cause for anxiety but who knows what his reasons are. I'm sure the chic would wonder what the hell was up if he did tell her though. Probably depends on the chic and what her values are. Even my dad said one time if you're a late 20's-30's male and haven't gotten any yet there's something wrong with you. Is there any benefit to saving yourself for marriage, for example? Does it really help with well being or anything like that? Stigmatizing a natural physiological function of human beings by hinging it on a man made institution is tough on the soul.