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Situation 805: “My friend met his soulmate on a dating site, a prison dating site”

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Hey guys! Ok I have a buddy who historically has the worst luck with women of anyone I’ve ever known. Sometimes, it’s just painful to sit back at watch it all unfold. Now, I think he’s setting himself up for more pain…and I’m wondering if it’s my place to step in and warn him. After “running out of options” he’s turned to a dating site dedicated to women behind bars. He says he’s been having regular exchanges with “Val,” who’s incarcerated in a facility over 1,000 miles away…and will be for five to seven more years…but he’s sure she’s “the one,” and is already planning multiple trips to “visit” her. If she is “the one,” then I’m genuinely happy for him…but, in reality, this feels like a disaster waiting to happen. How much latitude do I have here to be a real friend and risk crushing what’s left of his spirit? (email your situation to: listeners@957thebeatfm.com)

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