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First of all: your books and blogs are literally priceless. They have changed my life in a way I cannot even put into words.

I have a question that may seem a good problem to have but I want to do the right thing. I recently became single so I joined a dating site and found an amazing guy. He is insecure (anxious preoccupied) so things started a bit slowly. Just at the same time an old friend contacted me. He recently became single too and we reconnected. He is more secure so things went a bit faster with him. So I have been hanging out with both these men. I have a secure attachment style.

They are both literally awesome in their own way. I know I am well compatible with both and I am highly attracted to both. Both have done literally everything right and shown they care so much. They are both husband material and both have expressed the desire to get married and not have kids which is exactly what I want (I am mid-30s, never married and no kids). And both are asking me to be their girlfriend and be exclusive.

I told both that I would like some time to evaluate long term compatibility but I know I have to make a decision soon. I am not a cheater. My question is how do I word the inevitable rejection that one has to receive? I know honesty is the best approach to things but I don’t want to hurt either and I think saying I was hanging out with someone else will hurt a lot even if we were not in a committed relation yet.

I know neither was seeing anyone else because they told me (I always avoided saying if I was or was not seeing anyone else because I hate lying). They did not do a single thing wrong and I would totally date each of the two if it was not for the timing. So how do I let one go, in the most respectful way possible, once I make a decision? Thank you!


Dear Rose,

Yes, these are high-class problems, but they are problems nonetheless.

At this point in time, you’ve likely already made your decision (this blog has a 4-week turnaround time) and I trust that with your moral compass, you’ve acquitted yourself well and are now in a happy, healthy relationship with a new boyfriend.

But for all of the readers who have been confronted with a similar situation where you need to break it off with a perfectly nice guy who has done nothing wrong — the break-up speech itself is always a source of consternation.

I wrote about this recently, but it’s still worth revisiting.

First of all, if you’re breaking up with someone, you’re not doing anything wrong.

There is a huge difference between someone feeling hurt and you doing something hurtful. That distinction is important and a lot of people have a hard time differentiating between the two.

First of all, if you’re breaking up with someone, you’re not doing anything wrong.

No normal person ever wants to hurt someone; that doesn’t mean that millions of people aren’t hurt every day. That’s simply the consequence of different people having different opinions and different needs. It creates friction. How much friction depends on the people involved and their relative levels of confidence and communication. For example:

If my wife tells me she needs a night out alone without me or the kids, should I feel insulted? Someone thin-skinned might. But that wouldn’t mean she was insulting me. All it would mean is that she spends so much time being a wife and mother, she needs some space to reconnect with herself and her friends. Period.

Listen, I’ve made many people upset over the years both on and off this blog, and for the many thousands of interactions I’ve had, there are only a handful of times that I’ve actually tried to do something hurtful (out of pain or immaturity).

All the other times I’ve “hurt” someone has been because they didn’t want to hear my truth — or didn’t agree with it. That’s called collateral damage. I’m not intentionally inflicting pain on any woman who turns to me for advice, just because I challenged her original premise. Intention matters.

All you’re responsible for is speaking your truth as kindly as possible.

So when you tell a man that you like him but you don’t see yourself spending every day for the rest of your life together, he may perceive it as a slap in the face. But that’s on him.

All you’re responsible for is speaking your truth as kindly as possible: you like him, you appreciate him, you think he’s going to make another woman very happy one day, and he deserves someone who is all in on him.

Yes, he may be hurt, but at least you’re not doing anything hurtful.