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Tiffany writes:

Dear Deviled Angel,

My best friend of 10 years recently told me he’s in love with me and wants us to try dating.  He’s a great guy and it would be great except that since I’m his best friend I know everything about him.. including the fact that he used to fool around with men.  Granted this was years ago but I personally believe that if a guy fools around with another guy he’s simply gay.  I don’t want to bring it up and have him think I’m using what he’s told me in confidence against him or worse judging him.  It’s a deal breaker but how do I say that to him without losing his trust.


You can tell him the truth indirectly using finger puppets.  You’ll need a Boy Finger Puppet (BFP) and a Girl Finger Puppet (GFP) and use the following script (be sure to use a low voice for the boy and high voice for the girl):

BFP: I really like you.  We should date.

GFP: No, because you’ve tasted man-candy and you’re gay.

BFP:  Aw shucks.

GFP: Don’t worry we can still be friends and I won’t judge you.  Yaaaaayyy!!!



Who says you have to bring up his past history at all?  If you do bring it up you risk starting a defensive and unnecessary argument.  Start off with the positive:  Tell your friend how much his friendship means to you and that the last thing you want is to lose it;  but dating is just not the kind of relationship you want from him.  And leave it at that.  Should he press you for a reason just tell him you don’t feel the same way.  Then go grab a burger to lighten the mood.

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