Age Gap Dating Confessions

Tales of Taboo

Ali Weiss

Society & Culture

4.8 • 725 Ratings

🗓️ 26 June 2023

⏱️ 53 minutes

🔗️ Recording | iTunes | RSS

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Summary

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.

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 [email protected].

Transcript

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0:00.0	I'm Ali Weiss and I'm
0:19.6	obsessed with the people, ideas, and experiences that break the rules,
0:24.6	beat the odds, or are considered socially unacceptable.
0:28.6	And this is season four of Tales of Taboo.
0:32.9	Each week, I gather anonymous confessions from my listeners around the world who've existed in elusive
0:39.1	subcultures, ventured down the road less traveled, made serious mistakes, and achieved extraordinary
0:45.8	victories. Some of them call my hotline, and others will send written stories for me to read.
0:52.3	These stories are raw. They're honest and they're even
0:55.6	downright shocking sometimes, but they always deliver the most incredible life lessons and
1:01.9	encourage us to consider why we're also afraid to be different. And for season four, I'm introducing
1:08.3	a brand new twist. I'm starting each episode with my own,
1:13.1	no holds barred, on the record confession about the topic we're discussing. This week, it's
1:18.9	the world of age gap dating. Let's get into it. There's a man I've known for about 15 years,
1:32.2	who is now in his mid-60s, against all odds,
1:39.5	like him being a father figure to one of my best friends, living far away, being married, and literally twice my age, we've had this strange emotional connection for over a decade. We enjoy the same
1:47.1	books and have a similar sense of dark humor and could talk about anything for hours on end.
1:54.1	And, you know, he's sexy, which doesn't hurt either. But at the end of the day, none of these
2:00.1	factors actually explain why we have and
2:04.0	always had mutual chemistry against all of those aforementioned odds. It's beyond my understanding.
2:12.7	We've never acted on it for obvious reasons, but both of us agree that in another life, if he was
2:19.3	younger or I was older and we had like met in the late 90s or something, we easily would have
2:25.4	been together.
	...

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