Dump boyfriend who makes demands

Dear Carolyn: For the past two years, I have been seeing a man I care about very much. We’ve had a tumultuous, on/off relationship due to some mistakes I made early on that he couldn’t forgive.

Now he says he is ready to give the relationship another shot, with this caveat: I cannot EVER spend time with my best friend. He has met her only once, but never liked her due to a bad first impression and because I told him she participated in some illegal activities. 

While I don’t agree with some of her choices …

Dear Carolyn: For the past two years, I have been seeing a man I care about very much. We’ve had a tumultuous, on/off relationship due to some mistakes I made early on that he couldn’t forgive.

Now he says he is ready to give the relationship another shot, with this caveat: I cannot EVER spend time with my best friend. He has met her only once, but never liked her due to a bad first impression and because I told him she participated in some illegal activities. 

While I don’t agree with some of her choices, she has been a wonderful friend for my entire life. I feel he is asking too much, and has no right to demand this of me.

Is this an “OK” thing to ask of your partner? Or should I consider this a red flag of a controlling person? – Trouble in Tennessee

These are your words, so say them: “You have no right to demand this of me.” Controlling people exploit those who hesitate to stand up to them. (Homework assignment: “The Gift of Fear” by Gavin de Becker.)

Maybe this “best friend” is your drug dealer, to use one extreme example, and he’s right to set such a strict precondition – or, on the other extreme, your friend just did basic, stupid, youthful stuff. Either way, it serves both you and your boyfriend better for you to be clear about where you stand.

He has a right to dump you for refusing him, of course.

But I suspect he won’t. Those two “on/off” years, his reluctance to “forgive” your “mistakes” and this best-friend ban suggest he’s getting exactly what he wants here: a sense of control by giving and withholding affection to reward or punish you as he sees fit.

Since the drug-dealer scenario sounds like a stretch, I think you have to break up with him, decisively. It’s not that you’re above improvement – who is – or that your friend’s mistakes weren’t serious. It’s that he thinks it’s his place to fix you. How is that not controlling?