My best friend (let's call him Bob) is dating my girlfriend's best friend (let's call her Jen). Bob, at the age of 20, just lost his virginity to Jen. Bob is innocent and inexperienced, sexually and relationship-wise. Jen has a history of mental illness including bipolar disorder. She is extremely emotionally needy if not downright manipulative. Bob cares about Jen, but we feel this relationship is not in his best interest. He was well aware of her issues before this relationship began. I advised him not to get romantically involved with Jen.

When he gave his virginity to Jen, we were concerned that Jen was using him for another self-esteem boost and felt she had little regard for the fact that as a Christian, Bob had planned to save his virginity for marriage.

Right now Jen is angry at my girlfriend for real or imagined verbal slights, and she frequently vents to Bob about this. Bob then will often repeat to us what she says, trying to help. Bob has already admitted that Jen has accused him of not taking her side—although Bob has no desire to take any side.

Basically, we know what a drama-addict and need-freak this girl is, and we hate the thought of losing Bob as we know him. We know how kind and caring Bob is, and how difficult it will be to extricate himself from an emotionally damaged woman.

We're beginning to think we should formulate a plan to speed up the inevitable dissolution of this union, without lying if possible. Any ideas?

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He should know what is right and wrong. Let love take it's course.

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Find out if there is anything that Jen doesn't like doing (i.e. going to the beach) and invite Bob there lots. She'll end up nagging him to the death of the relationship.

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Thanks to both commenters!

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