How To Not Win Friends & Influence People

The other day we talked about getting stuck at the same point in the dating process over and over. Usually this occurs when it comes to dealing with what we perceive as conflict or resistance from the other person.

As much as many of us would like to get that person on the phone or in person so we can have what we believe would be a more productive conversation, we’re often stuck with email or text. And this would be where so many people end up shooting themselves in the foot. Electronic communication makes it hard to convey the appropriate tone or intention, and so we often end up putting someone off by our line of question.

I wanted to offer a few typical phrases and behaviors to avoid in these scenarios.


Please Explain

Someone recently sent me an email expressing confusion about an event location. She said that one page said one venue, another paid said another. She signed off with, “Please Explain.” Now, I’m sure she was asking me to tell her the correct location. (I did.) But closing with a demand – any kind of demand – tends to put people off. They very well might reply. Eventually. If they’re invested enough. But for the simple fact that you told them what to do, they’re going to make you wait. (I didn’t do this in my scenario.) Or they’ll just delete your message.

I Know You Think….

No, you don’t. And even if you do, nobody likes the idea that they are transparent. They will automatically go on the defensive. Presuming to know what the other person is thinking demonstrates your level of investment as well as your insecurity or tendency to project or overthink.

You Didn’t Do XYZ So I Assume ABC

This is a common one. The person never replies to your last email and drops off the face of the earth. You follow up just to be sure. “I haven’t heard from you so I’m assuming that means you’re not interested.” You’re probably right. But by admitting that you got their hint, you tip your hand. If you’re someone who has to know where you stand, admitting that you know they’re not interested makes you vulnerable to an “attack.” You’re telling that person that you’re choosing to subject yourself to being hurt. Find someone particularly cruel, and they will take this opportunity to hurt you more. The reality is that you have no idea what is going on in their life. Yes, they’re probably not interested. But there’s a slight chance they’re in a coma. Or just sick. Or busy. Don’t burn that bridge.

What’s Up With That?

No. Just…no. This is not something an adult should ever say.

Taking The Bait

Some people just want to get a rise out of you. If they can provoke you to be angry, they will take that reaction as a sign that they have a certain type of hold on you. Let’s face it…some people are toxic. These people will say intentionally provocative and inflammatory things strictly to get under your skin and hopefully stay there.


Whatever you do, don’t lie unless you are a) sure you’ll never get caught or b) really, really good at it. Definitely avoid elaborate, logically inconsistent lies that insult someone’s intelligence. Here’s the deal…you never know what the other person knows. In today’s world, where we’re all so accessible, all someone has to do is go to your Twitter or Facebook page. “You said you were so sick yesterday and that’s why you didn’t reply? So how come you sent 15 tweets yesterday?” or “You said you were dating someone else and that’s why we never met. So how come, every time I log on to OK Cupid/Match you pop up on my Favorites list as having just signed in?”  The liar ends up looking stupid and possibly crazy. That alone will make someone choose not to engage.

Repeatedly Emailing

There is absolutely NOTHING that works my nerves than someone who sends me multiple emails in a brief time period asking the same question. This sort of behavior screams self-absorbed. The world does not revolve around anybody. Send the email, wait 24-36 hours and then follow up. Do not…REPEAT…do not send multiple messages in a 24 hour period. That makes you look anxious and neurotic.If someone doesn’t answer you, it’s either because something more pressing is going on, they forgot or they simply don’t wish to engage you. By the 2nd email in under 24 hours, you automatically get dropped down the To Answer List.


I once had someone email me asking for the location of an event. I replied and gave them the name of the spot. They replied and said they didn’t have the address. I replied again and sent them a link to the page, as my laptop was on the blink so I had to use my phone to respond. Because they were using their mobile phone, the link went to a page that didn’t list the location. So the person replied back again saying they couldn’t view the page. I wanted to scream, “Google It!!!!!!!!!!!” But I didn’t. It’s my job to answer her, so when my laptop was up and running I got her the info she requested. If you can find something out on your own, do it. Insisting that someone – a date – meet some obscure and innocuous demand will make you look difficult.

I’d Prefer To Talk On The Phone

Never. Going. To. Happen. Once they hear that, they are going to intentionally stick to email so that they can control the conversation. They are going to avoid getting sucked in to a drama. If they do call, it will be when they are good and ready to call.

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2 Responses to “How To Not Win Friends & Influence People”

  1. Erin Says:

    Once again you have put together an outstanding list that benefits all of us in dealing with the various people of our lives! I know this is a dating site but truly so much of this pertains to everyday dealings with business associates, friends, family etc. I think if everyone tried to apply this list to their lives each day, they wouldn’t be so frazzled when they finally got around to the evenings and dealing with potential dates or significant others and life would just be a bit sweeter for everyone!!!!! YOU really do have a way of getting down to the brass tacks of what should be common sense. Unfortunately, we all have times when even as we hit the keys, or leave the message, we know we shouldn’t and hopefully this post will remind us to just stop and let it go!

    Like or Dislike: Thumb up 8 Thumb down 1

  2. fuzzilla Says:

    All excellent points, especially #5.

    I have a slight twist on #7 – nothing pisses me off more than when I HAVE answered someone’s question and yet they still keep asking it over and over again. They heard me, they just didn’t like the answer I gave and are hoping they can manipulate a different outcome through whining and dismissing/pretending not to have heard me. SO annoying and disrespectful.

    I should throw it back at them – “I have a question. Didn’t I just answer your question? And what was my answer?” (usually people who’d ask that are annoying enough to cut off all contact with, tho).

    Like or Dislike: Thumb up 5 Thumb down 1

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