I agree. Is it really that serious for a woman in her twenties to go out with him? Now I can see if she was running around publicly calling him the love of her life and getting Leo tattooed somewhere, but if he asks her out and she finds him attractive then I say go for it.
Leo definitely has a physical type and the fact that he gets older and his girlfriends stay roughly the same age does reflect that the guy may not be fully matured / totally self-actualized when it comes to romantic relationships, but whoopty doo, he is certainly not alone on this front there are several award winning directors, actors, businessmen who have a similar afflictions. New York and Los Angeles are lousy with blond model types, so I don't assume he cannot find a young, leggy blonde who is not an airhead. Don't get it twisted, of course Leo's modelizing is very snark worthy so keep the jokes coming, but IMO he still has another 10-15 years before he attains creepy, old man status and even then it will still be his prerogative to continue hooking up with young, leggy blondes.