4 Perfect Ways To Handle The Most AWKWARD Conversations With Men

It's all in how you say it.

how to talk to men Photo by Allef Vinicius on Unsplash

In dating, good communication is the key to meeting and attracting men … especially the right men. It's also the key to developing and maintaining fulfilling relationships.

When you love on purpose, you communicate on purpose.

One of the most important ways I support my coaching clients is by helping them communicate well with men. Online or offline, good communication requires certain knowledge and skill. It's a bit of an art, actually.


When challenging situations come up, I help women write a script that not only communicates effectively, but also feels comfortable and true to who they are.

Recently I helped my client "Kathy" tell the man she’s been out with four times that she’s not yet ready for intimacy. She was going to break it off with him, but I convinced her to try to tell him and see how it goes. He seemed like a great guy to me, and she was definitely attracted to him.

Kathy had that conversation (see our scripting below), and his response was, "Okay … I can do that. Thanks for telling me!"

There you go. Not only did she avert ending a potentially lovely relationship, but she earned his respect and opened up the possibility of further meaningful conversation. Well done!


Here are some other things I've helped clients with lately:

  • Showing a man she is interested without being too pushy. (Remember: Showing interest and taking the lead are very different things!)
  • Apologizing and showing regret for something she said.
  • Writing killer online dating messages and emails that get read and get responses.
  • Answering the question, “Why haven’t you been married yet?” when she goes on dates (Ugh…I used to get that question all the time! Guys: there is a better way to ask this.)

Here are specific examples you can use for some specific situations that might come up for you:


1. If you want to show a guy you're interested without being too pushy:

Instead of saying:
I'd like to go out. How about Sunday?

Say this:
I really enjoy talking with you. It would be great to do it again sometime.

2. If you want to tell a man he is going too fast and you are not ready for intimacy:

Instead of saying:
You're going too fast for me!

Say this:
I like you and I'm very interested in getting to know you. When I'm dating I find it works best for me to [fill in with how you would like to proceed]. How does that sound to you?

3. If you want to write killer online dating emails that are getting read and getting responses:

Instead of saying:
Hi. I like your profile. I see we have many things in common. Read mine and write if you’re interested.


Say this: 
Hi, Bob. I understand what you said about [thus-and-such], and I completely agree. (Agreeing with a man is very complimentary.) I [did something that shows you have something in common]. There's more to the story, and it's pretty funny. [Create some intrigue and set up for future conversation.] I'd like to know more about [something he has done]. Did you enjoy it? [Or some direct question that's easy for him to answer.]

I'm looking forward to hearing from you. [Show that confidence, girlfriend!]

4. If you want to answer the question "Why haven't you been married yet?":

Instead of saying:
It's none of your business" OR "because I haven't found the right guy yet".


Say this:
My life has been great but just hasn't gone that way yet. But I’m ready and looking forward to when I meet that terrific guy.

Communicating on purpose is actually not so hard as we make it seem.

And it creates an environment in a relationship where you're really loving on purpose. Most men want to understand us, and they want to please us. They just want a little help!


This is no different than learning how to communicate with your boss or that passive-aggressive gal at work. You need to learn some basics, and then you need to practice.

Do you see the pattern in all these? When trying to address a potentially difficult situation:

  • Be positive
  • Be direct
  • Speak from the "I"
  • Don't demand

Try these and tell me how it works for you!

Bobbi Palmer, founder of Date Like A Grownup, is an internationally recognized Expert helping women over 40 find grownup, lasting, passionate love with the right man. As a first time bride at 47, Bobbi shares in her free video series "The 4 Devastating Mistakes Women in their Search for Love" at DateLikeaGrownup.com.