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Episodes tagged: age difference

A horndog keeps dating ladies who don't want to have sex. Now he's…

Episode #99 —
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A horndog keeps dating ladies who don’t want to have sex. Now he’s bugging out. A nonorgasmic woman is making a lot of noise during sex, but she’s not closing the deal. How can she talk about it with her boyfriend? A gay man with a cute voice freaks out and clams up when faced … Read More »

Two tales of parental meddling: A woman is in a happily open relationship…

Episode #96 —
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Two tales of parental meddling: A woman is in a happily open relationship with her boyfriend. But her parents don’t know they’re both free to see other people. What happens when her dad catches the boyfriend courting another lady? Another woman is in a blissful relationship with a man 20 years her senior. But her … Read More »

We open the show with a couple of cute fellas who just can't seem to…

Episode #92 —
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We open the show with a couple of cute fellas who just can’t seem to meet people, despite their scorching hot looks and charming personalities. Does scat reduce (or increase) life expectancy? She’s digging him. He’s digging her. But she wants kids and he hates kids. What does their future hold? Cuckoo for cuckolding: Enter … Read More »

Down there hair: Must we remove it? Bad date: After a woman endures a…

Episode #89 —
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Down there hair: Must we remove it? Bad date: After a woman endures a super-creepy date, the fellow is still trying to contact her and pries her friends for info about her. How can she get rid of him? Is there something she should have done differently to give him the message? Unhappy endings? A … Read More »

The 34-year-old Dan Savage tackles the following questions: If you're…

Episode #88 —
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The 34-year-old Dan Savage tackles the following questions: If you’re into older guys, will you always be into older guys? Like even when you’re old? And is there anything wrong with that? What’s so very wrong with young people getting married, anyway? How can a lesbian swirling in lesbian psychodrama develop a bionic bullshit detector? … Read More »

Blood and Sugar: Today's episode spans many topics, including ladies…

Episode #87 —
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Blood and Sugar: Today’s episode spans many topics, including ladies who get compensated for their sweet time. One caller is falling in love with her sugar daddy. Another caller has a fuck buddy who has suggested that he pay her for her services; how much should she charge? A fit gay man has fantasies of … Read More »

He thinks he's a 61-year-old sex machine; she just likes the money he…

Episode #84 —
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He thinks he’s a 61-year-old sex machine; she just likes the money he pays her. Should she keep pretending to enjoy the oral sex her sugar daddy insists on giving her? • Clark Kent: Hear the charming but confusing tale of a couple who maintain both a real and online relationship with each other. • … Read More »

A former call girl is dating a conservative man. Should she tell him about…

Episode #82 —
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A former call girl is dating a conservative man. Should she tell him about her history with “compensated dating?” If you are a straight man, what is the polite way to reject a gay man? A woman who has been faking orgasms with her boyfriend wonders if she should tell him the truth now that … Read More »

Time limit: Her boyfriend says he loves her, but he's not "in…

Episode #71 —
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Time limit: Her boyfriend says he loves her, but he’s not “in love” with her. How long should she put up with this sort of nonsense? Bitch: If you think your buddy’s new girlfriend is a bitch, should you tell him so? What’s the etiquette here? Death by dildo: Hear the sordid tale of a … Read More »

Sisterhood is powerful. And so are blowjobs..

Episode #70 —
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Sisterhood is powerful. And so are blowjobs. A caller explains to Dan and all female listeners that a blowjob bestows tremendous power on the blower over the blowed. Lutheran jailbait: A teenage, “very, very Lutheran” girl living with her parents wonders whether she should tell them about her attraction to older men? A crossdressing man … Read More »