jul. - Dating Naked has offered up more than a few absurd moments of clothes-free courtship in its three-season history. (See: The penis pump salesman. Or the “wedding.”) And it looks like the romantic reality series is coming in hot this Wednesday. Meet Bob. He's 69 (stop it!), and he owns several carnival. My eureka moment as to 'why I dig older guys' happened this year. I went on a date with a guy my age (29 – graphic designer – cute – stupid name). During our post-dinner-quite-pissed-fumble-snog-sesh back at my flat, I took my bra off (seductively in my memory, likely awkwardly in reality) and he looked at my boobs with. mai - When it came to finding love in New York, Amber Soletti, a year-old who lives in the West Village, had no luck dating older guys or men her own age. While.