This week on Dating Diaries we hear of stories that cross the borderline, literally and figuratively. From a woman who treks 4,500 miles to reunite with her love to another who explores a new dating territory. And on top of that Dre and Ben unpack one of our craziest dating experiences yet!

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A single discovers her date has been to her place before with someone else in a really strange way. Season 1 favorite Theresa, a COVID healthcare worker, needs her medical skills for an emergency at home. And does LOVE mean learning to embrace your inner Michael McDonald? Experience all of the dating highs and lows with Dre and Ben without ever leaving your house.

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Dre and Season 1’s Kate and Mary talk about their speed dating experience through My Cheeky Date.

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Dre and Ben are back for Season 2. Some of us may be out of quarantine but life and dating is still a challenge as we adjust to our new normal. Dre and Ben dig in to fresh stories about singles looking for love in strange times. The hosts are haunted by an unprecedented ghost story. And we hear from a listener favorite who delivers an update and (as always) gives Ben a hard time.

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Dre and Ben dissect a listener's email regarding a complicated friends with benefits situation.

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Relationship therapist Dr. Nedra returns to illuminate the benefits of a crisis on love and personal growth. Plus, Dre & Ben sing Hamilton's praises.

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Dre and Ben unpack listener emails.

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We went to the mailbag. Listeners wrote in and brought tough questions to Dre and Ben for the candid, compassionate feedback that we've come to expect. We hear from a musician who can't get a moment of privacy, a woman who is flashes her hot connection then gets ghosted and a seriously infatuated guy who sends a milkshake to the yard of his love interest with mixed results. Plus Dre confesses to sliding into someone's DM's after a few too many. 

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Dre and Ben talk to Dr. Nedra Fetterman about the anxiety and emotional complexities of reentry.

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When you need a safe word to stay platonic, can you still really call yourselves "friends?” We speak to a single who has got it pretty bad for someone that is unavailable. Dre and Ben unpack how to handle major cultural differences and the importance of what it means to be truly invested in someone else. And government guidelines for safe sex during a pandemic?! Yep, Dre and Ben weigh in on that, too. 

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