31 Unique Things To Say To Your Ex To Start A Conversation (What To Say Without Being Awkward)

Last updated on February 12, 2024 by Michelle Devani

Are you struggling to have a normal conversation with your ex?

Do you wish you and your ex could continue to be civil with each other? 

Are you perhaps struggling to think of things to say to him? 

If so, this article is here to be your godsend. 

It features 31 nice things to say to your ex to start a conversation. 

However, before I reveal these epic conversation-starters, it’s important that you carefully read the following sentences.

It takes TWO people to make a conversation awkward. 

If you’re struggling to maintain a friendly connection with your ex, it could be because he has moved on.  

The tough thing about this is: he usually won’t let you know. 

Often, he’s worried about this triggering bad emotions from you that he simply doesn’t want to deal with. 

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On top of that, you’ll see what online services he’s using, what contact details he has registered and a lot more.

Put simply, this tool should reveal some clues as to how he really feels about you. 

There’s no chance of him finding out that you’re tracking him - so what is there to lose? It could be the key to understanding this strange new relationship you have with him. 

My list of 31 good conversation-starters should also help.


Things To Say To Your Ex To Start A Conversation

Are you trying to figure out the best things to say to your ex to start a conversation? 

That can be a challenge, especially if you haven’t talked to each other in a long time or if you are trying to get your ex back. You don’t want to come across as too needy or desperate, but you also want to get your point across - a tough dilemma. 

One thing you should consider is how you left things. Was it a mutual breakup, but you haven’t talked in a while? How did the two of you leave things? 

In this post, we will discuss that situation, as it is important when considering what you should say next. You don’t want to start with an “I love you” if the last thing you said was, “I hate you!”

Also, there are some things that may help you as you decide how to first approach your ex after a long period of time. There are also times when it’s just a really bad idea to talk to your ex. We’ll take a look at all of those things in this awesome article on how to start a conversation with your ex!

How Did You Leave Things?

Once two people have broken up, there are many stages in that new relationship. It may be that you say your ex weeks ago but were not on speaking terms. Are the two of you ready to talk again, perhaps in a casual way? If you think the time to talk is here, but whatever you say will be out of the blue, you can gently approach your ex again, casually, of course.

Have you stayed friends with your ex? That’s another stage many ex-couples go through. If you are on good terms, it may be time to move things to the next level, meaning you could ask him out or try to gauge his interest in you by seeing if he’d be willing to move things along. This will give you a good idea of what he is thinking about you right now. Is anything more possible?

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Finally, if you think there are many unresolved issues, it may be time to talk about those problems. What went wrong in your relationship? Make sure you don’t play the blame game here; instead, explain what you think happened and the part you played in the breakup. Talk about how you’ve changed and what you would like him to know about you now. 

Conversation Starters If You’re Talking Out Of The Blue

conversation starters if you're talking out of the blue

1. You will never believe where I am right now.

This is a great way to show your ex that you still think about him and want him to know it. You have given him an opening to say, “Where are you?” If he isn’t interested in talking to you again, he will probably say nothing, and you can just move forward with your life.

2. I just started doing something you might find interesting.

Maybe you’ve taken up karate or kickboxing and know he’d get a kick out of it if he only knew. It’s okay to say something like this to show him you want him to know what’s going on in your life today. This may give him the opening he needs to speak to you.

3. Do you remember what we did last Christmas?

Maybe the two of you share an inside joke that happened on Christmas, or maybe the word Christmas just makes you both bust out laughing because of what happened. Remind him of the good memories you shared, and he may really want to chat with you. Just be patient; he may not respond right away.

4. You will never guess what I am doing at the moment!

Did he always hope you would take a cooking or baking class? Now that you have signed up and are into baking mini-muffins, he should know all about it, right? This is a great opening for a really fun conversation! He’ll definitely text or email you back!

5. Something just reminded me of you!

Maybe you were at the mall and saw green cotton candy, his favorite, or something like that. Whatever it may be, you are showing him you still think about him and that you just wanted him to know that. If he feels the same way, he’ll start talking to you again.

6. Can you tell me more about something?

Asking an open-ended question is a great way to make your ex speak to you again. Unless he is super bitter about what happened, he’ll take the bait.

7. My family asked about you the other day.

This is another great conversation starter. You could mention that they were wondering if the two of you still talked. Tell him that you were hoping you could start talking once again. If he’s interested, he’ll jump on the opportunity. 

8. I just heard a song that reminded me of you!

Give him a chance to ask you what song that was, and your conversation is started!

9. You will never believe who I just ran into!

Isn’t it great having mutual friends or acquaintances with your ex? This gives you the perfect chance to strike up a conversation with him. 

10. Guess what my new passion in life is!

guess what my new passion in life is

What did he always hope you would enjoy doing? Maybe he tried to convince you to go skydiving a million times, but you never had the courage. If that is your new passion, let him know! He’ll be impressed!

11. Did you see the game last night?

Breaking into some small talk is okay when working on getting back on track with your ex. Talk about current events or even just the weather if nothing else exciting is going on. 

12. How is your mom doing? I was just thinking about her.

How can he pass up on this question? He won’t just ignore you. 

13. Do you remember this?

Remind him of the cute memories you shared so that he will be curious as to what’s on your mind. Say, “Remember that time we went to the candy store at the mall?” Maybe you had a special memory that day; let him remember the good times you shared.

14. Were you at the mall yesterday?

Whether you actually saw him or not, this is a great opener. Your ex will feel obliged to answer you to let you know where he was and when. From there, you can talk about anything. 

15. What’s new with you?

This open-ended question will get him to think about why you are curious about him. He’ll enjoy letting you know what’s going on; after all, who doesn’t love to talk about themselves and their life?

16. Can you recommend a good sushi restaurant?

This is a perfect conversation starter. You are asking him an open-ended question that he will enjoy answering. Who doesn’t love to give their opinion on something?

17. I was just thinking about you yesterday!

This one says it all right there. Just be honest and ready to answer more questions he may throw your way!

18. I saw on social media that you are doing something new.

What a great way to get him to talk about his new passion or hobby! If it’s new to him, he’s probably still pretty excited about it!

19. Can I get your expert advice on something?

People love giving advice, so this little opener can really get his attention! Just be ready to answer if he asks what you need. 

Conversation Starters To Take Things To The Next Level

conversation starters to take things to the next level

20. Do you still like olives? There was a sale, and I ended up with a ton of them!

If you know what the favorite food of your ex is, you have the perfect opening with something like this. Just send him a text like this, and he’ll be interested in responding.

21. Our pet sure would love a visit from you if you are interested!

Yes, it’s a tad bit manipulative; you may feel guilty for saying it, but it’s probably true if you bought the pet together! This way, he’ll have an excuse to see you if he’s interested in doing that.

22. Are you up for a little chat?

Don’t get caught off guard with this one. Make sure you are ready to talk and ask plenty of questions that he will enjoy elaborating on. 

23. I was wondering if you’d be interested in a casual date with me.

If you think everything is going well with your ex, there’s no harm in asking him out. Just be prepared for rejection or no answer at all. Think that it’s just not meant to be if he doesn’t respond the way you’d hope.

24. Can you help me out with something?

Guys love helping girls out, even if they aren’t romantically involved. It makes them feel important. Plus, what a great way to get to see him again!

25. Our band is coming to town. Interested in checking it out with me?

Another way to ask him out on a date; you are acting like he’s doing you a favor by going with you, which may make him feel like he’s got to go to keep you company!

26. Would you be up for coffee or lunch this week?

He may be super excited about doing this. It may not bring you back together, but it’s a good start. 

27. I need a date for my office holiday party. Would you help me out?

This is another great way to convince him to see you. You don’t have to make a move on him, but it would be nice if he went as your date, so you could see each other again.

Conversation Starters When You Want To Talk About The Breakup

conversation starters when you want to talk about the breakup

28. I really think you are due an apology. I am very sorry for what I did.

This is always a positive thing to say to an ex when a relationship has ended. It never hurts to admit you were wrong. He may have been waiting a long time to hear you say those words. It may not bring you back together, but it could help you both heal

29. I completely understand why we needed to break up now.

This comment may intrigue him, especially if you were in the wrong. Your ex may not want to get back together right away, but he’ll probably enjoy hearing what you have to say on the subject.

30. I’ve really turned over a new leaf and want to tell you more.

One of the best ways to start a conversation with an ex is to talk about your new life, how happy you are, and what you have changed. He would probably love to hear all about it, and you can share all the new developments in your life. Let him know that the negative aspects of your life have changed dramatically and explain how. 

31. I realize where we went wrong, and what was my fault. I am sorry.

Another way to tell him you are apologetic for your part in the demise of your relationship. Just let him know that you don’t expect anything in return; you just wanted him to know this information. 

How And When To Best Approach Your Ex

If you are hoping to reconnect with your ex through conversation, Psychology Today recommends coming toward him from a stance of strength. This means that you work on yourself; do some serious self-reflection to determine what role you played at the end of your relationship. Where were you wrong? What could you have done differently?

Wait to approach your ex until you feel better about yourself; have a clear vision of your faults and work on them. Show your ex you have changed for the better. When you get into a conversation with him, tell him about the improvements you have made. If you are unsure where to get started, it’s a wise decision to see the help of a trained professional. 

They typically have the tools and ideas you need to get started. If you can show your ex (after some serious self-help/self-improvement) that you realize your mistakes and have changed, you will really get his attention. He may want to consider getting back together if you have improved in the areas where he thought there was a problem. Not all relationships can be saved, though.

When You Should Not Contact Your Ex

when you should not contact your ex

If you were in a toxic or abusive relationship, it’s not a good idea to have a conversation with your ex. Do you really want to repeat the same mistakes over and over again? That’s basically the definition of insanity. If you were in an unhealthy relationship like one of those, you should probably just leave the relationship in the past. 

Likewise, if you were in a relationship where physical or emotional cheating took place, it also may not be a good idea to talk to your ex now that things are over. Could you really ever trust him again after him doing that to you? What kind of future do you really see for the two of you? Is there any way in which a conversation with your previous partner would help?

The only time I would suggest talking to your ex after the end of an unhealthy relationship is if you were the one who was the problem. If you had anger issues but have done extensive counseling to work through those problems, you could explain to your ex in a conversation how you’ve changed now. Just don’t walk back into an unhealthy situation where nothing’s changed. 


How do you start a conversation with your ex?

The best way to start a conversation with your ex is to just be casual with what you say. Don’t start the conversation with a threat or accusation about something he or she may have done. This isn’t the time for the blame game. Instead, be easygoing about everything.

What to say to an ex to hurt them?

I wouldn’t advise going after your ex-boyfriend with the intention of hurting them; that won’t make you feel good about how things ended between you two. If you really want to hurt them, you might talk about your dating life since the breakup. That always stings for exes.

How can I seduce my ex over text?

Be coy, witty, and funny; flirt a little bit by saying things like, “Guess what I’m wearing?” or “What do you miss the most about me?” Talking about sex is one way to get guys’ attention. Keep in mind that he may not be ready to talk yet.

Can I tell my ex I miss him?

I think it’s appropriate to tell your ex-boyfriend that you miss him if you want him to know that information. There’s no guarantee you will get back together just because you say that, though. If you are okay with that possible reality, go for it! Tell him about your feelings!

How do I make small talk?

Keep up to date with current events; what are people chatting about today? Watch a news program or read a newspaper so you can show you are up to date on what’s going on. These things will give you something to talk about that’s casual, appropriate, and preferably not controversial.

To Sum Things Up…

Are you talking to your ex, hoping the two of you will start toward a path on getting back together? I can’t guarantee you will get your ex back if you follow these conversation starters, but it is a good start! What do you plan to talk about? Please comment!

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Michelle Devani
My name is Michelle Devani, and I've been helping people with their relationships since 2003. In 2017 I decided it was about time I started a blog on the topic, and since then more than 2 million people worldwide have read my relationship advice. Drop me a comment below to let me know what you think.

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