He Keeps Talking About His Exes!

Posted by in communication skills in dating, love after 40, red flags in relationships | 2 comments

he keeps talking about his exDear Sandy,

I’ve gone out for over a month with a man who keeps talking about his exes on almost every date. It makes me feel uncomfortable, especially because he doesn’t talk about how he feels about me. Should I wait it out or is it a red flag that he is still thinking about these girlfriends from the past?


Dear Kay,

You’ve only been dating a month, so I’m not sure if you’re exclusive or whether you’ve slept together. If you’re just dating casually and he keeps talking about his exes, it can be annoying, but it’s not necessarily a red flag. If you were exclusive and had been dating for several months and he still talked about his exes, I’d be more concerned.

Is it a red flag if he keeps talking about his exes?

Some men talk about their exes because they don’t have closure. They’re still hoping to get back together. They’re still in love their exes. Those men are not emotionally available for a relationship with you. This is a definite red flag, and I would break up with that guy and search for a man who has left his exes where they belong – in the past.

However, some men just like to talk about their exes, even when they have no intention of reuniting with them. I’ve been on dates with divorced men who feel the need to talk about their ex on a first phone call or a first date. They don’t want their ex back, but they feel the need to talk about her. Sometimes they’re still angry, and want to let you know that they’ve been hurt, cheated on, and stripped of their finances and dignity.

With men like that, I’d say it’s a yellow flag. They still have some emotional baggage they need to deal with. It can be draining to listen to him spew negativity about an ex. That makes him a victim, which is a relationship repellant. However, this type of guy might be able to curb the complaining if you speak up early on in the relationship.

I wouldn’t “wait it out”. I’d have a conversation, even if it makes you uncomfortable. Better to speak your truth than tolerate behavior that makes you feel bad and wait it out. You might say something like this:

“John, is this a good time to talk? (Always check in with someone before having a difficult conversation. Make sure they’re open to hearing you and can be attentive. If he says “Yes”, continue the conversation. If he says “No”, ask when would be a better time.)

I am very attracted to you and have enjoyed getting to know you over the past month. I noticed that you talk about your exes a lot. I prefer to stay present in my relationship with you. The past is the past. I’ve learned so much from my past relationships, and I’m excited to share my new and improved self with you! How about you – what have you learned?”

Keep the conversation positive. Keep the focus on the present and future, not the past.

What concerned me was that you said, “It makes me feel uncomfortable, especially because he doesn’t talk about how he feels about me.”

If he’s focused on the past and he’s not attentive to you and he doesn’t make you feel cherished and special, that is a red flag. He might be hanging out with you because he feels comfortable with you, but he doesn’t truly care about escalating the relationship.

Do you feel safe with him? Do you feel that he truly cares about you? Are you seeing each other regularly, and talking frequently on the phone? If not, it’s probably time to move on.

Make sure you are a high value woman first, a fabulous girlfriend second. Don’t tolerate being an option or just a sounding board.

Have that conversation with him and see how he responds. If he gets defensive, that’s a bad sign. If he thanks you for letting him know how you feel and promises to do better, he’s got a good chance at being your boyfriend.



For a copy of Sandy’s FREE report, “The Top Three Mistakes Midlife Daters Make (and how to turn them around to find love now)” please click here.

‘Like’ Sandy’s  Facebook page for inspiring posts on dating and relationships & links to her weekly radio show.



  1. This is great advice Sandy–it can be difficult to speak up sometimes but the continuing talk about ex’es feels like a slow poison that puts me in a place of doubt. Not good!

  2. Kay, speaking your truth can be very scary, but it’s a muscle that gets stronger with use. Start as soon as you can. Speak up when you feel hurt with everyone in your life. I once had a coach who said, “If you don’t have the words yet, just say OUCH.” Very powerful. Here’s a video I made about the Power of Ouch a few years ago. https://www.youtube.com/watch?v=6eLdbXQKxFs


  1. Tips For a Successful First Date - When Men Pull Away - […] unnecessary, regardless of how positive or negative it may be. Even though many people do use the ex-talk a…

Leave a Comment

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.