Should you meet a stranger or a friend for the first time?

My wife and I have been discussing having sex with someone else lately, and she keeps bringing up a friend of mine. We've known each other for twenty years and drink together all the time. I feel uneasy about dating him, worried it might make things difficult later. But my wife is also worried about dating a stranger. I'm really torn. I'd appreciate any advice from you experienced folks. Thank you.

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Should you meet a stranger or a friend for the first time?

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