dating, social skills

Dealing With Rejection Part 3: How to Reject Someone Skillfully

A man who is actively dating will inevitably meet many different types of women during the course of his week. Especially in any urban environment, a man who is focusing on his social life will come into contact with dozens of women every month. But many of these women will not be a match for him, for many reasons, and he will inevitably need to say so to some of them.


There’s a lot of advice out there on how to break up with someone gracefully and honorably. My own personal value system when it comes to breakups comes from the principles of non-violent communication, which can be found here. What I’m speaking about in this piece is what we need to do when we first meet someone who clearly isn’t who or what we were looking for. You’ve gone on one, two, or three dates with this person, and you need to let her know that you don’t want to see her again.

My own personal value system again requires that I stay positive and send the woman back out into the dating pool having had a good experience and a generally positive outlook towards men. Understand that to risk going into awkward social situations, to say nothing of the physical risks that come with blind dates or internet matches is, for a woman, incredibly courageous.  At the same time, its not my responsibility to educate her or take care of her feelings. Some women will take rejection badly no matter what you do. My goal is to create a clean break with no regrets, and to leave the woman feeling good about the prospect of meeting someone else, whenever possible.

When is rejection necessary?

It’s not always possible, or even desirable, to actually tell someone that you don’t want to see her again. You don’t need to reject someone you’ve just met if:

  • She consistently fails to respond to your texts or messages
  • She was dishonest at her first interaction with you (ie, lying significantly about her age, her looks, or her marital status)
  • She was cool to you at the initial meeting, and expressed no desire to see you again
  • She was obviously filled with excessive drama at the first meetup or talked too much about subjects inappropriate for a first or second date (i.e. family court issues or obsession with an ex-boyfriend or ex-husband)

Needless to say, excessively rude behavior on a first date leaves absolutely no obligation on your part. Show zero tolerance for lengthy cell phone conversations over dinner, extreme criticism of everything you do, or nasty behavior towards waitstaff. Feel free, in those situations, to go to the bathroom and not come back, or just walk out mid-meal.

You do want to reject someone clearly and compassionately if:

  • she’s someone who wants a different type of relationship than you do
  • someone unsuitable contacts you again
  • she’s someone you’ve slept with at any time

The goal is to leave no doubt that you don’t want to see her again while at the same time giving her just the right amount of information for this purpose.

Five things:

  1. It’s not your job to educate her or give her insight on why you’re rejecting her. Once, when I was seeing someone filled with a lot of drama, my dating coach said to me, “Don’t spend a lot of time on damaged women. It’s not your job to fix them.” Cold, but true. A man with healthy boundaries and self-esteem is not going to spend lot of time with women who drain his energy after just one, two, three dates.  This includes correcting her false impressions about you.  There will be times when you should let her be free to misunderstand you or your intentions.
  2. “Honesty” is overrated.  Too many men give themselves permission to behave cruelly towards a woman, under the notion that the honesty is a good thing.  I’ve been mortified by statements that have been repeated back to me by women friends who were rejected brutally after one or two dates.  These men thought they were being honest, but they were really just being insensitive cads.  Don’t tell her you’re looking for someone younger.  Don’t tell her she gives lousy head.  And for God’s sake, don’t tell her you find her overweight or unattractive.  She’ll figure it out, or not.  Again, it’s not your job to teach her.
  3. It’s OK to soften the blow with a compliment.  The “you’re am amazing woman” prelude is overused, but for good reason:  it works when you mean it.  It’s not only a signal to a woman about what’s coming next, it’s a reminder to her of her good qualities.  Be sure to be specific about what’s amazing about her — in one or two words.
  4. Always start with a phone call, not a text message or an email.  I am kind of old-fashioned this way.  If she’s worth a formal rejection, she’s worth a phone call.  Sometimes she might not answer; it’s OK to leave a voicemail or send a text with what you want to say, especially if she’s someone you’ve met only once.
  5. It’s also OK to write out what you have to say in advance.  There’s no shame in doing this, especially if these kinds of communications are new for you.  If you’re seeing her face-to-face you should memorize it; otherwise, you can just read it out loud in a call or text it to her.  Keep it short and sweet, and remember the above points.

Rejection is inevitable.  But rejecting a woman gracefully brings good karma.  Remaining positive and creating a clean break will leave her with a positive impression of men, and leave you feeling good about getting back out there.


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