Age Gap Dating Confessions

Tales of Taboo

Couples with large age gaps can cause polarizing reactions. On the one hand, age is a number and love is love - it knows no bounds or rules. Should one be lucky enough to find it, it’s always worth diving into head first, no? On the other, when one partner has lived considerably more life, is it kosher to subject a less experienced and often more impressionable partner to their baggage? Is desiring a younger woman implicative of some emotional deficit?

I open this week's episode with my own candid confessions about seriously dating a 35 year old when I was 22. I was mature then, but certainly not a grownup - and while I know he loved me, I look back now and realize how my youth and naïveté were taken advantage of by somebody who wasn’t ready to face adult responsibilities. Then (9:53), our anonymous confessors call and write in with stories about their own male partners who were or are considerably older. The age gap ranges from 13 to 31 years, with a variety of dynamics: boss-client, boss-employee, pilot-flight attendant, Shibari rope partners, and regular old meet-cutes. From navigating Viagra, party stamina, and awkward public PDA to step-children and ex-wives, our contributors hold nothing back in revealing the good, bad, and ugly realities of cross-decade (even inter-generational!) dating.

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Tales of Taboo is produced and narrated by Ali Weiss. Follow Ali on Instagram & TikTok @aliweissworld. Audio production by Isabel McMahon & WTF Media. Theme song by Chris Stathopolous. Cover photo by Erika Flynn. Cover art by Kristen Montenegro. GOT A SECRET TO GET OFF YOUR CHEST? Share your own confession - or thoughts and feedback - at [e-mail].