I don't think this is something I would ever even think about doing, the discomfort factor would be too high. Not to condemn anyone who would, it's just not something I would do. For those who would and have done it I think there are some circumstances to consider, like if he dated your friend for a week or something that's one thing, if they had a year-long relationship (or something along those lines) I think that may be crossing a boundary.
Love,
Me
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