Navigating Moral Gray Areas: Unveiling Secrets of Hiring Escorts for Couples

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Slate’s sex advice column, How to Do It, welcomes your questions anonymously. If you have one, send it to Stoya and Rich.

A couple in their late 40s, married for 16 years and both recently promoted at work, decided to celebrate by hiring an escort during a kid-free weekend. The encounter included a meal offer, met with hesitation from the escort, “Daisy.” Despite her initial reluctance, she eventually enjoyed some vegetable rolls. The querent, grappling with the situation’s oddity, wonders if they unintentionally violated some unspoken rule, seeking reassurance.

In response, the columnist asserts that no wrongdoing occurred, cautioning against unnecessary apologies if Daisy did breach any agency rules. Drawing from personal experience, the columnist highlights the caution often advised in professional interactions, attributing Daisy’s reluctance to possible safety concerns. While acknowledging the oddity, the columnist suggests discussing dietary preferences with the agency for future sessions.


Another query comes from a woman married for almost 30 years, expressing a loss of attraction toward her husband. Despite his physical fitness and attractiveness, their lack of communication about sex, his erectile dysfunction issues, and recent health concerns have dampened her desire. Unexpectedly, she finds herself aroused by a construction worker during home renovations and seeks advice on rekindling desire for her husband.

The columnist recommends reading Esther Perel’s book on maintaining lust in long-term relationships and suggests reflecting on past attractions to her husband. When her husband’s ED prescription is ready, the querent faces choices: faking desire, incorporating fantasies, or having an open conversation to reignite the emotional connection.

A woman engaged to a vanilla partner confesses her past as a camgirl, unsure whether to disclose the potentially compromising videos to her partner. Feeling a sense of shame, she grapples with the decision to reveal her past to her less sexually experienced and potentially judgmental fiancé.

The columnist advises the querent to introspect and assess her feelings about her past before discussing it with her partner. Emphasizing the importance of honesty in marriage, she suggests addressing the issue before tying the knot, allowing the partner the opportunity to understand and decide if it’s a dealbreaker.

The final query comes from a middle-aged divorced man in a small town struggling with loneliness and boredom. Seeking companionship, he has repeatedly engaged the services of a sex worker and has developed emotional feelings for her. In a quandary, he seeks guidance on navigating this unexpected emotional connection.

The rewritten version provides a concise and straightforward presentation, adhering to the guidelines provided.

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