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When I say “real” cubs I mean the men that actually want to date older women instead But don't make them feel like you're just scratching something off the list. Have conversations with whatever older women you might be attracted to? But telling an older woman you are attracted to older women might get the eyeroll so I. I briefly dated a woman who was 42 when I was She taught me so much about pleasing women. It didn't last long because she just wanted a younger guy for. I'm 25 and would love to have just that one experience with an older woman. all over his bathroom floor, he was smoking and drinking the ENTIRE date.