Dear Justine,

I’m a 26-year-old woman and my 29-year-old brother and I are both JDaters.  He dates a lot and admits that he’s sort of a player; I’m much more romantic and selective. 

We exchange dating advice a lot.  One thing we argue about is how to break up with someone you’ve gone out with just a few times.  I think honesty is the best policy and that I owe someone a face-to-face break-up, and an explanation of why it won’t work out.  He thinks explaining what went wrong only leads to unnecessary hurt feelings; he likes to keep things brief and tell the girl what he likes about her instead of what he doesn’t like.

Who’s right?


Justine’s Answer:

This is an age-old Men are from Mars, Women are from Venus argument… and you’re both right.

I agree that you owe someone you’ve gone out with more than a couple times a face-to-facer.  But your brother would probably agree with me that it doesn’t need to be at a restaurant over a five-course dinner. Your date probably doesn’t want to hear an hour-long explanation of his shortcomings, and you don’t really owe him that.  This is a breakup, not a chat with your English professor about the problems with your paper.  Plus, being around others who can hear your conversation would be awkward and painful (flagging down the waitress when you’re both feeling sad, wondering who picks up the check, blinking away potential tears, etc.).

A park bench is a good bet. 

I’m not going to script your breakup for you, but here are some pointers: Keep it short.  If the guy wants to hash it out, so be it, but it’s ultimately worse for both people to drag out the agony.  You say you like to tell your date what went wrong and your brother likes to calm hurt feelings with compliments.  A mix of both can be ideal:

  • “It’s sweet that you’re attentive, but I just don’t have time to take all your phone calls.”
  • “You didn’t dress up for our dates, which made me feel that you weren’t trying hard, but I liked that you had spontaneous, cool date ideas.”
  • “I loved that you put such an effort into dressing up for our dates, but I just didn’t feel chemistry.”  

Of course, by listing areas for improvement you’re giving your date a chance to plead his case and say they’ll change.  And it’s probably a lost cause, as the annoying stuff probably wouldn’t have mattered to you as much if you were more into him.  But, I agree with you that giving your date feedback is a humane thing to do when you end things, because otherwise he’ll be left pulling his hair out about what went wrong. 

Make no mistake: if your date gets super needy (“Can you please explain why it’s such a problem that I didn’t dress up for dates?”), you don’t owe them an intense explanation.  You’re stating honest preferences and you don’t need to defend yourself.  And if your date gets mean, game over!  This is why your brother will approve the park bench venue!

There’s no perfect, totally clean way to do this.  It’s rough to be rejected by someone you like, even after a short time, and its rough to hurt someone’s feelings.  But, hopefully you’ll come away from the conversation feeling like you’ve done right by your match and that person will come away from the conversation feeling like they understand what went wrong (and also armed with a couple of compliments to soothe the blow).

Justine Borer is a family and matrimonial lawyer practicing in New York City. In her spare time, she loves to write, act, do pilates, and spend time with family and friends.
One Comment
  1. My favorite is hearing “It’s not you it’s me” I am soon tempted to say in reply “Well done if it IS you are you dropping out of JDate until you change?” But as my sisters tell me that is a ladies to give the sugar with the vinegar that is rejection.

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