If friend keeps asking, she either wants validation or the truth
Q: A good friend of mine is living with a guy, "Adam," who I can't stand, to the point where I try to avoid hanging out with her when he's there. My husband and other mutual friends feel the same. It's not just that he's a jerk; we can see he's totally controlling of her as well.
She seems to sense that he rubs people the wrong way, and asks me from time to time, "What do you think of Adam? You can be honest." Or asking what my husband thinks of him, in the same way. I usually flub my way through it because I feel terrible telling her I don't like him.
Should I be brutally honest with her? A previous boyfriend of hers was also disliked by all. After we all breathed a sigh of relief post-breakup, she constantly said, "Why didn't you guys tell me how much you hated him!?" She is contemplating marriage. I want to be honest, but don't want to ruin our relationship if she ends up with him forever!
A: She has asked you more than once to speak up in the context of an old relationship, and asked you more than once to speak up in the context of this new relationship, and you want to speak up, and you're still asking whether it's okay to speak up. I guess I'm wondering what it's going to take to pry loose your Adam concerns.
Which, of course, are ultimately concerns about your friend and her pattern — so please frame them that way: "You've asked me a few times about Adam. Are you having reservations?" Listening is never a bad strategy when speaking is problematic. Plus, if she doesn't bite and instead turns the question back at you, you get to say you do have concerns but are hesitant to speak. That will give her (yet) another chance to show you if she really doesn't want the truth — and that's what you suspect, isn't it? That her quest is for validation, not truth? It's a legitimate concern with any friend, but particularly for one showing signs of insecurity.
She probably sees signs that Adam is trouble, just as you do, but may be invested in not hearing a truth that will necessitate another breakup with another not-too-nice guy, followed by the humiliation of another audible sigh of relief from her friends. Yet that's why you must take her at her word that she wants to know what you think. You say you don't want to "ruin our relationship," but that's about protecting yourself from a loss. If Adam really is controlling, then please make it a priority to help her find what she seeks.
Slip of the tongue warrants one of two forms of an apology
Q: Hanging out with my boyfriend and some of his friends, I accidentally let slip to one of the friends' dates that he has been seeing someone else, who I thought was his serious girlfriend. Major drama with the friend and his date, and a lot of anger was directed toward me. Truthfully I'm not really sure what the status of his relationship is, so I shouldn't have assumed anything. Did I screw up, and should I apologize?
A: If you concluded from this guy's dating habits that his girl-du-jour needed a rescue, then you'd owe an apology for being presumptuous. Accidents do happen. If you did just step in it — "it" being the friend's apparent deceptions — all you owe is an "Oops, sorry" and an unspoken "Good luck with that."