Mailbag: How to leave a casual relationship

by GK on December 15, 2011 · 6 comments

It’s mailbag time, boys and girls! The question comes from a new friend of mine, SW of Philadelphia, who is wondering how to tell a woman he’s dated several times that he’s no longer interested, while letting her keep her dignity and letting him remain free of stab wounds.

SW’s mini-crisis boils down like this, and I hope you’re better with numbers than I am: He started off seeing Girl No. 1 for a while. While he was seeing her, he simultaneously met Girls 2 and 3 online, and he particularly hit it off with Girl No. 3.

So well, in fact, that he wants to focus on Girl No. 3 and cut ties with the other two. “Having to break it off with a girl I’m not even official with …  it’s uncharted territory for me,” SW said.

Here’s the rest of his story:

Maybe for some guys they’re fine to just stop texting, and not answering the other girls’ texts, but I cannot do that. I don’t want to keep them hanging on when I don’t foresee a future with either of them. I actually just got a call from (Girl No. 2) tonight and we had a great conversation, but I could not bear to wait any longer.

I explained that I really appreciated the opportunity to meet her in person and had a great few conversations getting to know her, but that I met someone else and felt it unfair to them to go on a date when my feelings have gotten stronger for them. And also not fair to waste her time. She was more than appreciative and said, “I’ve been in that situation – on both sides of it, and been led on. Thanks for being honest, its a rare quality sometimes and I hope you the best, I really am happy for you, that’s what this is all about!”

Whew, one down. One to go. Unfortunately, (Girl No. 1) will be tougher, because we’ve been intimate … I would feel better letting her know I am grateful for our time together but I must pursue someone I have very strong feelings for. And hope it’s not too harsh.

I’ve done some evolution on this subject in recent years. I used to think it was OK to silently leave a girl I was seeing unless more than one of these factors applied:

  • We’d had sex.
  • We were bound to run into each other again.
  • She was trying to contact me.
  • We’d gone out more than a few times.

My thoughts changed after I ignored one girl I’d seen twice, and she wrote about it on HER dating blog (it’s almost a rite of passage to get slammed by a female dating blogger in San Francisco — they’re everywhere). I was only half-contrite when I wrote about it two years ago, but in hindsight, I was wrong. Since then, I’ve always responded to women, and they’ve always appreciated it. It’s good karma, and I haven’t received a single ice pick in my eyeball.

Actually, SW, you’ve answered your own question. What you did with Girl No. 2 couldn’t have been classier, and you could see that in the way she responded. I recommend a similar phone call with Girl No. 1 where you tell her exactly the same things. You don’t need to say anything different just because you slept with her. As long as you keep your cool and stay respectful, she’s likely to do the same.

I can help you better if I rattle off what NOT to do. I’ve been guilty of some of these offenses earlier in my legendary dating career:

Don’t arrange a date to tell her: You might think it’s more personal to do it this way, but you’re really just wasting time. Why make her get dressed up to see you, only to ambush her the way Michael Corleone kills Sollozzo in the first “Godfather”? One gentle phone call is all it takes, and you won’t need to ask permission to get the gun from the bathroom.

And definitely don’t arrange a date where your friend dumps her for you. That’s just weird:

Don’t give her a long explanation: The shorter your conversation, the better. A simple “I don’t feel enough of a spark” is good enough in most cases. If you find yourself having to convince her the way George Costanza did, you’ve gone too far. (“Seinfeld” has many classic breakup scenes. I could write a post just about them.)

I’m a big fan of giving her the Nice Sandwich: Start off with something positive, like how much fun you’ve had getting to know her. Then for the meat of the sandwich, tell her you need to stop dating, giving her one brief reason. Then top it off with another positive piece of bread, such as telling her you wish her the best. That’s a tasty sandwich.

Don’t tell her you’re sorry: You have no reason to be — these things happen every day — and acting like you’ve done something wrong might encourage her to make a scene.

Don’t tell her you want to be friends: That is, unless you really DO want to be friends. Though Rob Overman disagrees, I’m all for befriending women. But we’ve all been on the business end of that cliche, so unless you’d really hang out with her without having sex, don’t use the F word. If you’re not sure, you can always look her up later.

Don’t have sex with her right after: That kinda defeats the purpose, doesn’t it? And it also might give her hope. If it’s a friends-with-benefits situation you’re looking for, that’s for a different mailbag.

Don’t insult her: You may think she wants to get serious with you, but accusing her of that might piss her off, even if you’re right. Best to borrow from the Big Four and talk about yourself: It’s not that she’s trying to get serious with you, it’s that you feel like you’d be leading her on if you keep seeing her. She can’t argue with your feelings.

And that’s all I can tell you, SW. I don’t feel like I can give you any more advice on this topic and I don’t want to waste your time. It’s not you, it’s me.


1 SW December 15, 2011 at 10:28 am

Thanks for the mailbag post GK! I’m glad you also think I’m doing the right thing. It may seem obvious to some people to avoid the “DON’T DO THIS” bullet points, but maybe not for others.

Luckily, I didn’t do any of these with girl #1 or girl #2. (Yes, I did contact girl #1 the night before last). I applied the same formula because it went so well with girl #2. Unfortunately, after I was done with my “compliment sandwich” as I like to call it and saw your wonderful reference of it in the post above, I got silence and crickets. Followed by she’d ‘prefer to not hear from me again.’

I guess some people really are hurt by being let go and no matter what you do, you cannot ease their pain even if it was a brief time together. The sad part is that she did try to turn it around to say I was the bad guy that lead her on, but I firmly believe that leading her on would be just the opposite! – Not telling her how I feel up front, and letting this hang on for the next few months – Now that’s leading someone on. At least in the way I understand it…

I guess you can’t win ’em all with trying to “do the right thing”, but I think it’s for the best for all parties involved. I’m a person who believes when something is right, you act on it and do it right. That’s how you get the happily ever after.

I hope things continue to work out with dating girl #3, as they have been. GK, as always my friend, your advice goes beyond your words. Thank you so much!

2 GK December 16, 2011 at 3:23 am

Thanks for the update, SW. It’s too bad she took it the wrong way, but sometimes, even when you do the right thing, you’re going to be the bad guy to some people. That’s life.

Anyway, keep me posted on Girl No. 3!

3 Barry December 20, 2011 at 9:11 am

Hey Gk, quick question. And apologies for going off topic completely. I’ve been having a dry spell lately (for several months) so I was thinking of considering a slumpbuster as you previously mentioned. Is it a good idea? Thanks, Barry

4 GK December 20, 2011 at 11:22 am

That IS off topic, Barry, but I believe in the magical powers of the slumpbuster. So as long as nobody knows and you won’t be seeing her around, I say go for it. :)

5 Barry December 20, 2011 at 1:53 pm

“I believe in the magical powers of the slumpbuster.”
Can I ask why? No disrespect meant, but am I not giving into frustration by doing so? I agree it gets you back in the zone or so, but maybe rediscovering where I went right or wrong in previous attempts could be more productive. I don’t mean to be an ass (which I am being) but I guess I feel by doing so-considering a slumpbuster-I’m admitting defeat!

6 GK December 21, 2011 at 1:21 am

Hey Barry, I decided to make a full blog post about this for you. Enjoy!

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