How to Talk to Your Ex-Boyfriend

Updated December 12, 2019
Couple drinking coffee at cafe table

Once a relationship has come to an end, basic small talk can feel a little awkward. If your goal is to win him back, you'll need to be intentional about how you communicate. Even if you're not looking to rekindle an old flame, good communication skills are useful if you want to remain friends after a break-up.

What to Talk About

Focus on talking about anything other than why you broke up, assuming you've already had that conversation, of course. Even if you haven't, chances are, you both know why you split, and dwelling on the negative past is not the way to win him back or gain any traction on rebuilding a friendship. Instead, find other topics to discuss that hopefully will not lead to a ton of pregnant pausing and awkwardness.

Stay Neutral

Whatever you do, your primary goal should be to stay neutral. Don't ask how he is doing. He's either doing great, in which case you might not want to hear about it or he's doing horribly, which leads to the inevitable awkward. Neutral questions include information that is not about you or him. For example, if you run into him at a mutual friend's wedding or party, ask what gift he brought for the guest.

Tell a Joke

One of the best ways to get people to feel more comfortable is to make them laugh. Have a funny story about something that happened? Share it! Got a punny one-line joke? That is definitely fair game. Of course, be sure to avoid inside jokes that remind him of shared memories. Shoot for making him laugh without taking a stroll down memory lane.

Ask 'You' Questions

One trick to try to avoid awkward silences is to ask 'you' questions. Questions that focus on your ex, forces him to talk about himself. You do want to avoid the generic, 'How are you?,' but you can ask things like, 'What have you been doing?,' 'What is new in your life?.' If you happen to know specifics, like a new job, or a new hobby, ask how he likes it. This way, you can get a conversation going. Pro tip: if you want him back, be genuinely interested and actively listen.

Ask About Interests

Try to remember something he's really into; that one thing that causes him to talk animatedly and ask about it. Whether it's work, his pet or a hobby, if you can find a way to bring it into the conversation and get him talking - bonus for you. It has the added benefit of ensuring that you don't have to talk too much either - thus avoiding any sticky situations.

Mutual Acquaintances

Two people who once dated usually share at least some of the same friends, so this is a safe topic to bring up with your ex in general conversation. However, you want to steer clear of talking about relationships in general, including the relationships of your mutual acquaintances. A great question might be something like, 'Wait, have you seen so-and-so? The last time I saw him he was...' You can use this and ask about his family as well.

Master the Art of Paraphrasing

It might sound odd at first, but if you sense the conversation is going into boring territory, try paraphrasing and then asking a question. For example, he tells you he has a new job. You can say, 'Oh, that's exciting that you have a new job? Is it similar to what you were doing before?.' Or better yet, ask him if he likes it.

Two women sat on wall

What Not to Bring Up

Just as some topics shouldn't come up in polite conversation, some subjects are taboo when you're talking to your ex. You don't want to bring up a topic that is going to provoke old feelings of disdain or aggravation. The goal is to avoid things that are too emotional or serious, especially during those first few encounters. A few things not to talk about include:

  • Don't talk about why you parted ways or past mistakes. This is old news and has already been hashed out.
  • Don't keep apologizing for any wrongdoings on your part when the two of you were still together. Again, leave the past in the past.
  • Don't tell him you want to get back together. Even if you want the relationship to begin again, you don't want to sound too needy.
  • Try to avoid talking about too many shared experiences, inside jokes or other things that are reminiscent of your relationship. Even if those things are positive, it makes it seem like you aren't moving on.

How and When to Talk to Your Ex if it's Been A While

If you haven't spoken to your ex in a while, you may wonder when an appropriate time is to begin contact again. If you've left on good terms, you can opt to begin contact more quickly than if you ended the relationship on more difficult terms. Think about:

  • If you were the one who ended the relationship, make sure you and your ex have both had enough time to process the situation before beginning to reach out. This could mean waiting weeks to months and testing the waters before resuming speaking terms. You can do so by sending a quick message noting that you would like to begin speaking again and asking your ex if they feel the same way.
  • If the relationship ended on bad terms, make sure you've given yourself and your ex enough time to heal before attempting to re-connect. If you were in a relationship for just a few months, wait a few weeks before attempting to chat again. If you were in the relationship for a year or more, give yourself a few months to fully process the situation before deciding if re-connecting is the healthiest choice.

Speaking After a Few Months

If you've gone a few months with sporadic to no contact, enter into the relationship again slowly and keep in mind that your ex may not be open to chatting. The best way to re-connect on a friendly level is to be upfront with your ex regarding what you want relationship-wise and asking how they feel about it. If they agree to begin chatting more regularly, start off slowly by connecting on topics that you know your ex enjoys speaking about and catch up on your day-day lives.

Speaking After No Contact

If you've gone a period of time with zero contact, you'll want to re-initiate the relationship very slowly. Keep the topics of conversation light and spend some time checking in on what's been going on in each other's lives. If all goes well, you can begin to connect again on deeper and more serious topics. Continue to evaluate whether re-connecting is the healthiest choice for you and be open with what type of relationship you'd like to have moving forward with your ex.

Calling Your Ex

One of the best demonstrations of how the phone is misused in dating is a scene in the movie The Swingers. In a desperate attempt to get his girlfriend back, one of the lead characters leaves message after message. What starts as comedy quickly turns to tragedy as you beg the character to have some self-respect and stop calling. Even if you don't leave tons of messages, you can still abuse the phone.

One simple rule to remember when you want to call your ex and strike up a conversation is not to call unless you have a good reason to do so. Therefore, the best way to initiate a phone conversation with your ex is to find a logical reason to call. A few examples of reasons to call would include:

  • You have a specific question about something. For example, you need to know the name of a hotel you once stayed at or an event you were both involved in.
  • You have a reason to congratulate him, such as you just learned he enrolled in college or landed his dream job.
  • You have questions or concerns about one of his family members or a mutual friend.
  • You need his advice on something he is familiar with, like a problem with your car or how to make a certain food.
  • You found something of his he may want back. Say you've been holding onto one of his shirts. Calling him up to get it back to him could be a good conversation starter.
Young man on his phone

Avoiding Awkwardness in Phone Conversations

Talking on the phone with an ex can feel a little awkward and at some point, the discussion may run dry. Remain positive throughout the call; think of it like a job interview. You don't want to go into great detail about emotional things yet. If you attempt to manipulate his feelings by crying or sounding depressed, your tactics will only turn him off. If you get on the phone with your ex and the conversation starts to go dead or get awkward, try to steer the conversation toward general, less-serious things:

  • Local happenings (if you're in the same locale)
  • Mutual hobbies
  • Ask about a recent event that pertains to a shared interested (ie did you see the game last night, or the new movie, etc.)
  • Share a funny story
  • Ask about upcoming vacations, especially if it's close to a typical vacation time

The nice thing about the phone is that if it's really awkward you can tell him you have to go, but set up another time to talk.

Texting Your Ex

For some, it takes a lot less nerve to grab your phone and send off a text message than it does to call your ex and have to hear his voice. Texting makes it much easier to communicate without tripping all over your tongue and fumbling with what you mean to say when you try to speak out loud. Also, a simple text is a good way to get the conversation started. A text can also feel less threatening to your ex.

Texting is easy enough, but it's important to remember four basic things:

  • Start with something simple. A basic, "Hi, how are you?" is sufficient. Don't dive in and start sending page after page of text. To him, this may feel like you are coming on too strong.
  • Choose your words carefully. Words are easier to misinterpret than a conversation because there are no verbal cues. You don't want to send an innocent message and have him perceive it as something other than what you really mean.
  • Wait for a response before you text again. This one's a biggie. Don't keep rattling off text messages begging for a response if you don't get a quick reply after the first message.
  • Try to move from text messaging to interaction over the phone. Texting is nice, but talking on the phone is a little more personal, so you will want to get to the point when you call him, even if it takes a few days of simple messages.
Texting with cell phone

Communicating With Your Ex Online

The internet provides some pretty easy and straightforward ways to connect with your ex. You could always drop him a line or two via email, reach out to him on social media, or even tag him in a post on a social media feed. This easy-access communication can make it easy to do or say something without giving it a lot of thought, however. So there are rules you should follow.

Treat online communication the same as the conversations you would have on the phone. Only email him when you have something substantial to discuss. Also, don't send him another message until he responds to your first email. Allow him the opportunity to pursue you again.

In-Person Conversations

Hopefully, the phone calls, texts and emails will result in an eventual face-to-face conversation. How should this touchy situation be handled? The fact is, a first-time face-to-face meeting with an ex can have you feeling like a bundle of nerves like it's the first time the two of you have ever been together. Treat this meeting almost like you would a first date and keep these tips in mind:

  • Wear something that makes you look awesome. While you obviously want to dress for the occasion, there's nothing wrong with reminding him you're beautiful.
  • Sport some confidence. Whether it's affirmations or a pep talk from a girlfriend beforehand, do whatever you need to do to come off confident.
  • You may want to talk about new things going on in your life, but you do not want to talk about your new man. At best it's insensitive, at worst it can come across as petty.
  • Keep it short. If the meeting is planned, schedule something shortly afterward so that you have to leave. Scheduling something so that your meeting is short will help ensure that you can put some distance between you and him to regain perspective. If things go well, you can always meet again.

Much like a first date with a stranger, keep the conversation lighthearted and casual, steering clear of things that may bring up hard feelings. Keep your emotions in check and avoid being all googly-eyed and touchy-feely no matter how close the two of you once were. The first few face-to-face encounters need to be low-key and easy, not serious and emotional.

Enjoy His Company

When you do get a chance to talk to your ex-boyfriend, be your normal, charming self. Don't try too hard to get him back; you may seem desperate, and desperation isn't an appealing personality trait to anyone. If you want to recollect on the history the two of you share, be sure to only bring up the good memories, and not why you broke up, or what you think he did wrong when you were together. Treat him as you would a friend. Whether you want to keep him at friend status, or go back to being something more, you'll be more likely to succeed.

How to Talk to Your Ex-Boyfriend