110 Questions to Ask Your Ex

Some people never want to see their ex again, some hold out hope for a reunion, and others simply enjoy maintaining sporadic contact. It depends on the relationship. Regardless of where you are on this spectrum, exploring specific questions to ask your ex is important because it invites certain conversations that can give you perspective on your relationship and how it ended. 

Asking right questions allows you take greater control of the way you emotionally process past relationships with your ex and get a clearer picture of how you both perceived the relationship and where it all started to go wrong. While the answers to answers to these questions can sometimes be painful or challenging to work through, asking questions is often how you ask for closure, bringing an emotional resolution to your pain and filling in those informational gaps that often torment us post-relationship.

There are different types of questions that you can ask your ex after a breakup, depending on the kind of tone you want to strike and what you’re hoping to get out of the conversation. For instance, deep questions can explore their outlook on your relationship and dating in general, while funny questions can help summon some playful nostalgia, creating a better atmosphere for more emotionally demanding questions. Let’s explore some of the types, what they hope to achieve and some question examples.

Questions to ask your ex boyfriend

These are the kind of questions that relate more strongly to how men can often process their emotions after a breakup. Although these are also general questions you can ask an ex of any gender, men can have a harder time expressing their feelings and have distinct coping strategies compared to women when dealing with a relationship ending.

A study published in the Social Sciences journal found that while women often have a large support network of friends and family that they rely on to explore their feelings and gain an outside perspective, guys were more likely to neglect their network and rely on themselves.¹

So, by asking your ex boyfriend questions that speak more to their opinion of material aspects of the relationship, you can begin to access some of the emotions they may be keeping locked inside. You’ll often get a positive reaction, creating a sense of catharsis for men, as these are often topics no one else in their life has helped them work through.

Here are a few things you could ask:

1. What was your favorite memory of us together?
2. Do you think we brought out the best in each other?
3. What did you learn about relationships from being with me?
4. Do you think we ended things too soon?
5. What was the happiest moment you had with me?
6. What’s one thing you always appreciated about me?
7. Do you think we ever really understood each other?
8. If you could change one thing about our relationship, what would it be?
9. What’s one thing you miss about being with me?
10. Do you think we’ve both grown since our breakup?    

Questions to ask your ex girlfriend

The types of questions you ask women after the end of the relationship can often be more direct and emotionally charged because women are generally better with self-disclosure.² This isn’t universal, though. Studies have found that people’s attachment style and who initiated the breakup have a more profound effect on behavior than gender.³

Unlike men, some of the questions that you ask an ex girlfriend will often be things they’ve already explored with their closest friends and family, which can make them slightly more resistant to reopening those topics. But try to remember this is about you getting perspective and closure as well. In a sense, they do owe you an explanation for some basic aspects of the breakup.

You can get them in the right headspace to discuss other issues by giving them a heads-up first, letting them know the kind of conversation you want to have so they don’t feel ambushed. You could also try opening with different types of questions that touch on nostalgia, their experience of events and the feelings that speaking about them summons. 

Here are a few examples to get you started:     

1. What’s something you valued most about our relationship?
2. Do you ever think back on the good times we had?
3. What was your favorite thing we did as a couple?
4. Do you think we communicated well?
5. What’s something you learned about yourself from dating me?
6. Do you think we were compatible in the long run?
7. What’s one moment you’ll never forget from our time together?
8. Did I ever do something small that meant a lot to you?
9. What do you think was the highlight of our relationship?
10. Do you think we could have done anything differently?

Questions to ask your ex after a breakup

These are the things you ask right after a breakup. This can be after a week, a couple of days later or can even come up as soon as you’re finished breaking up, if things aren’t too heated at that moment.  

These are some of the most important questions you can ask your ex. They often deal with the functional aspects of how you’re going to handle the breakup and the boundaries you want to set regarding making contact. It can also help shed some light on a few things you might not be clear on about the breakup, if the end felt rushed or too emotionally charged to discuss things calmly at the time.

It’s important to make these questions broad and somewhat dry so they don’t inflame the situation or introduce further conflict. Here’s how you could try approaching them.

1. Do you think we ended things on the right terms?
2. What was the hardest part about breaking up for you?
3. Do you think we made the right decision?
4. What’s something you wish you’d said before we ended things?
5. What’s one thing you miss about being with me?
6. Do you think we both handled the breakup fairly?
7. What do you think we both could have done better?
8. Do you still think about us sometimes?
9. What’s the most important lesson you took away from our relationship?
10. Would you ever consider being friends in the future?

Questions to ask your ex for closure

In terms of a relationship, closure is ultimately a resolution to the notion of someone leaving your life or the nature of your relationship changing. It puts a definitive emotional end to things. While closure may not help you heal immediately, it allows you to more fully accept the situation and kickstarts the real healing process.

The key aspect to closure is a lack of ambiguity, which is why it’s important to work on the questions that you ask your ex, to find this closure, so you can see whether they’re addressing the core misunderstanding and any sense of ambiguity that is truly stopping you from moving on.

Without closure, it can be very difficult to begin a new relationship. Even if you do, it may be hard to find happiness with someone else because you can’t fully emotionally invest. So, if you’re struggling with uncertainty, confusion, and residual feelings for your ex, try some of these questions or use them as inspiration to explore your own emotional state and how you can personally achieve closure.

1. Do you feel like you got closure from our breakup?
2. What do you think was the biggest reason we didn’t work out?
3. Do you think either of us gave up too soon?
4. Was there something I did that hurt you more than I realized?
5. What do you wish I had done differently?
6. What do you think you could have done differently?
7. Do you think we’ll ever truly understand why we broke up?
8. What do you want me to remember about you?
9. What was the hardest part of moving on for you?
10. Do you think we were right for each other at the time?

Questions to ask a cheater for closure

A partner cheating on you can feel like an intensely devastating betrayal. It’s difficult to forgive, let alone begin to get over. However, it is something you will eventually need to deal with or it can cause lasting damage to your concept of intimacy and trust.

Whether you choose to leave your partner as a result or decide to try to move past it together, asking them questions about the why, is how you get to the root cause of what factors caused it. Establish whether it has anything to do with you and how you can avoid it or spot early warning signs in the future.

As you’re figuring out how to ask for closure, remember two things. Firstly, some people just cheat, regardless of their relationship quality. A study from Brunel University of London suggested that certain people may be predisposed to it on a genetic level.⁴ Secondly, looking for clarity is not an attempt to excuse their behavior. You should explore the following questions as a way to heal yourself, not placate or give closure to the other person.    

1. What made you decide to cheat?
2. Do you regret cheating on me?
3. Was there something missing in our relationship you didn’t talk about?
4. How long had you been thinking about cheating before you did it?
5. Do you take responsibility for what happened?
6. Do you think you’ll ever cheat again in another relationship?
7. Was there something I did that pushed you away?
8. What do you wish you had done instead of cheating?
9. Do you think you truly loved me while you cheated?
10. What would you say if someone did to you what you did to me?

Romantic questions to ask your ex

Romantic questions help you reminisce about the good times you had with your ex and discuss the connection you once shared. This can include questions that are very specific to your relationship and shared experiences or a general question that unpacks how they’ve been dealing with the relationship’s end and what moments were particularly memorable for them.

To be clear, by asking your ex romantic questions, they’re very likely to get the impression that you’re thinking of rekindling things or, at the very least, are open to exploring the idea. If this isn’t your intention, it’s best not to broach the topic or you may end up confusing them, which isn’t fair to your ex.

But if you are open to it, romantic questions can be a great way to test the waters with an ex while simultaneously inviting a nostalgic energy into conversation by stirring up older, warmer emotions that they once felt for you. Here are some general examples to help get you started.        

1. Do you remember our first kiss?
2. What was the most romantic thing we ever did together?
3. Do you ever miss the little things we used to do?
4. What’s the sweetest memory you have of us?
5. Do you still think about the first time we met?
6. What made you fall for me in the first place?
7. What was your favorite date we ever had?
8. Do you remember the first time you told me you loved me?
9. What’s one romantic thing you’ll never forget about us?
10. Do you ever compare new relationships to ours?

Serious questions to ask your ex

While it can sometimes be uncomfortable or painful to explore, past relationships are an invaluable source of insights into how others interpret your approach to dating and intimacy. Exploring the right deep questions to ask your ex is the ideal way to unearth these insights constructively.

The only problem is that not all their insights are going to be positive. It can take maturity to react in a healthy way, without sparking an argument about pedantic details or how your respective versions of the relationship differ. That’s why it’s best only to ask serious questions like this after a decent period of time has passed since the breakup.

Try to take their answers at face value. It’s just one perspective of many. If you feel certain answers were fair, then let it help inform and improve how you handle future relationships. Try the following questions and see how they react to them. From there, you can take the conversation to more specific and sensitive areas.

1. Do you think we were truly compatible?
2. What did you learn about love from our relationship?
3. Do you think our breakup was inevitable?
4. What was the hardest part of our relationship for you?
5. Do you think we could ever have worked out long-term?
6. What do you think I misunderstood most about you?
7. Do you think our timing was wrong?
8. What’s one truth about us you never shared before?
9. Do you think our relationship changed you?
10. Would you ever want to talk more about what went wrong?

Flirty questions are much like romantic questions in their intention but distinctly more playful and less deep in their approach. The general aim here is simply to get a dialogue going with your ex again while making it obvious that it’s for romantic rather than platonic or nostalgic reasons.  

Asking your ex flirty questions lets you reestablish sexual tension and mutual attraction more casually. It does this a way that expresses more than you’re thinking of them, rather specifically looking to get back together.

If you come on too strong, it may come across as strange or emotionally tone-deaf. Start with something small, see what they say back and build on it from there. Here are a few instances of how you could open the conversation with some light flirting.

1. What’s one thing you always found attractive about me?
2. Do you miss my hugs or kisses?
3. What’s your favorite memory of us being playful together?
4. Do you ever think about our chemistry?
5. What’s a flirty thing we used to do that you liked?
6. Did you ever brag about me to your friends?
7. What’s the cutest nickname you had for me?
8. Do you remember a date night that felt really special?
9. What’s something I did that always made you smile?
10. Do you think we still have some spark?

Juicy questions to ask your ex

Juicy questions let you get right to the point with your ex by asking for the complete truth about something, either about your relationship or their current dating activity. These are a bit like deep questions, exploring the nature of your connection, except juicy questions ask for quite a lot of honesty and disclosure.

For this reason, asking your ex questions like these can very easily backfire if they still have lingering resentments towards you or you haven’t contacted them for an extended period. Think of it as extreme closure. You’re going to find it but probably a lot more rapidly and aggressively than you may have anticipated or be comfortable with.

But they are incredibly effective at breaking through those reconnection rituals with exes and getting the information or perspective you want. If you’re mature enough to handle some answers that might not be complimentary or even somewhat emotionally raw, they are indisputably useful.

You can try one of these but do proceed with caution:

1. What was the most fun we ever had together?
2. Do you miss our late-night talks?
3. What’s something you never told me while we were dating?
4. Do you think we had good chemistry?
5. What was your favorite inside joke we shared?
6. What’s the most romantic thing I ever did for you?
7. Do you miss how we used to laugh together?
8. What was the most unforgettable trip or date we had?
9. What’s a secret you kept from me while we were dating?
10. Do you ever compare your new relationships to ours?

Silly questions to ask your ex

By coming up with some funny questions to ask your ex, you’re not just helping ease any initial tension but also extending an olive branch of sorts, inviting them to reexplore fun old memories and reform some kind of bond by sharing humor again.

Being funny and laughing with someone is such an important trait in a relationship that one study found that people take noticeably longer to get over a humorous partner and that women in particular are much more likely to re-initiate contact with a funny ex.⁵      

This isn’t alchemy, though. Humor is an ancient bonding tool, coping mechanism and emotional regulator. We place a lot of social value in humor and default to it when we want to connect while keeping ourselves protected, making it an effective ice breaker.

Here are some silly questions you could ask to get through your ex’s defenses.

1. What was the silliest fight we ever had?
2. Do you remember the weirdest thing we ever did together?
3. What’s the funniest nickname you gave me?
4. Do you remember any embarrassing moments we shared?
5. What’s the weirdest thing we ever cooked or ate together?
6. Do you remember a time we laughed so hard we cried?
7. What’s the dumbest inside joke we had?
8. Do you remember the funniest trip we took?
9. What’s the most ridiculous thing we argued about?
10. What’s a silly memory you still laugh about today?

Questions to ask your ex to get them back

Let’s be honest, getting back together is often the reason people look for questions to ask their ex to begin with. Many of the types of questions we’ve explored are effective for doing that, in that they reestablish a connection and encourage dialogue between exes.

However, as the interaction continues, sometimes a more direct approach is necessary for reconciliation. This is either because you’re stuck in a friendly-but-distant-conversation mode or they simply aren’t picking up on your hints.

You will likely have to show that you’ve changed somewhat, are flexible enough to improve on the things on your end that originally broke you up and possess a general enthusiasm for approaching the relationship differently.

Let’s look at some purposeful questions you can ask to make your intentions clear and indicate a willingness to work on the connection.

1. Do you think we still have feelings for each other?
2. What’s one thing you miss most about being with me?
3. Do you ever think about giving us another try?
4. What do you think would be different if we got back together now?
5. Do you think we’ve both grown since the breakup?
6. What would it take for you to consider us again?
7. Do you ever compare others to me?
8. Do you think our story is really over?
9. What’s something you’d like us to do differently if we tried again?
10. Would you ever consider rekindling our relationship?

What to talk about with your ex

Once you’ve gotten past some initial questions and you’re exchanging messages or calling each other, you’re going to want to keep the conversation going with different things to talk about with your ex. Here are some interesting topics to explore.

• The big update – Catching up. It’s like small talk but for people who know each other well. What’s happened in your life since you last spoke? How are your respective families doing? It’s not exciting but it does express interest in their life and an enduring affection for them.      
• Shared connections – Everyone likes a bit of gossip. You likely shared some friends and social connections during your relationship, which you may have even needed to divvy up when you ended things. Now’s a good time to dish on anything juicy that’s been happening lately with those people or to just compare notes on what you both know.
• Recent events – You already know each other’s tastes and interests, so talk about recent things that have been happening in those areas. For instance, their favorite recording artist’s new album or how bad the new season of that series you used to watch together is.  

• Your feelings – This is a somewhat bold topic that you should work your way up to over a conversation. Discussing each other’s current emotional state or residual feelings leftover from the breakup can go in unpredictable directions. But this is often the kind of topic that creates enough energy to put you back into the space of exploring getting back together.

How to start a conversation with your ex?

Let’s look at a great way to maintain or re-establish positive communication channels with your ex again.

• As we mentioned, questions are a launchpad into interesting new topics, creating their own conversational momentum. But don’t keep asking different questions if it doesn’t seem to be working.  
• Only ask your ex open-ended questions, which tend to invite longer, descriptive answers.
• If you still follow their socials, you could ask them about a specific post they made that seemed exciting (like a trip overseas or a career change), either congratulating them or asking more about it.
• Open with a message instead of a call. Something light in tone and not too text-heavy, just to test the waters. Once the conversation gets going, you can stay on text, if that’s what makes you comfortable, or just suggest calling them.
• Tell them what you miss about them but in a less obvious way. For instance, you could tell them you miss cooking together, quietly playing Sudoku while sitting together in the park on Sundays or even their adorable cat. This will come across as more platonic and personal while avoiding a needy or desperate tone.  

• You could always use the tried and tested line for contacting exes again: “I was doing [formerly shared activity] the other day and it really made me think of you. How are you doing and what have you been up to lately?”

How to ask for closure from an ex?

Asking for closure can sometimes be a more difficult conversation to have with an ex. It often involves dredging up the past and reexamining your relationship problems, which can be emotionally challenging for some. 

• Ask them if it’s okay to contact them first.
• Suit the message to their personality and communication style. For instance, if they have a more reserved personality, they may work better with a series of short questions to ask your ex than one very broad question like “Why did we break up?”
• If they don’t answer, try sending a full email or even a paper letter. It creates more emotional distance and doesn’t put them in a corner. It also shows them that you really want to get some answers for your own mental well-being but you respect them enough not to cross their personal boundaries to get them.
• Make it very clear that it’s something you need to heal. And this is true. A study found that closure and understanding the reasons for a breakup helps us reframe our emotional state and build better relationships going forward.⁶
• Give them time to process and answer. They may not have the same urgent need for closure or could be nervous about reinitiating contact. Assure them that it’s purely to get some perspective on the breakup and moving on healthily.
• If you don’t receive an answer, don’t push it further. Try to find closure on your own terms, either with the help of a therapist or just by leaning on your support network. 

Where your ex has found someone else is often something that rests at the top of someone’s mind post-breakup. It’s part of the process of closure. He’re how to get that conversation started.

• Before you ask them, understand that it will signal that you’re interested in the idea of getting back together.
• Don’t dive right in. Start out with a short message reestablishing contact and asking your ex some questions about how they are. If they don’t even answer this, they definitely don’t want to discuss their personal life with you.
• If you’re feeling nervous about asking directly, then just ask how their dating life is going in a casual tone. If they’re seeing someone, they will want to let you know, even if it’s just to inspire a bit of jealousy.
• Don’t ask them to compare you to their current partner. Firstly, if they were with you longer and this is relatively soon after the breakup, it’s a rebound relationship and you’re the more important chapter in their life story. Secondly, even the kindest answer to this will hurt your feelings.
• If they are with somebody and you want them back, just ignore the new partner and take the shot, honestly. Put your feelings out there. It will still be painful if they say no but at least this way, you just ripped the bandaid off, got closure and now you can move on. 

How to ask your ex to get back together?

Depending on how you’ve been interacting since your breakup, asking someone to get back together can be a good or bad idea. Here are the ways to assess the situation and your own feelings about it. 

• The first step to getting back with an ex starts with you. You should ask yourself if this is what you really want or if you just want them back because being alone is more painful right now than being in a bad or mediocre relationship.
• Avoid doing it if less than a couple of months have passed since the breakup. You’re not thinking clearly at this stage and it’s too short a time for anything that caused the breakup to have really changed.   
• Establish contact first and feel the vibe out for any residual affection or warm emotions. The tone and content of this initial interaction will give you a solid idea of their general feeling towards you.
• Prioritize making amends for the reasons you broke up or those resentments will simply fester and ruin any chances of this fresh attempt going anywhere good.
• Once you feel you’re in a good emotional space together, just ask them. That’s the best you can do, so if they still say no after trying to repair the connection, they really just no longer have a desire to be with you.   
• If it’s a no, don’t push the issue. You can’t hard sell a reconciliation. Respect their answer, cease contact and move on. 

What questions should you avoid asking an ex?

Anything that you think will cause unnecessary tension as you rebuild the connection. But there are certain bad questions that you ask your ex almost as a reflex because you’re exploring the relationship. Here’s what to avoid.

• What really happened the day we broke up? – You know what happened. The last moment you should want to rehash with your ex is the rock bottom moment in your relationship. It’ll either seem like you’re trying to dodge any accountability for the breakup, or like you want to gaslight them into remembering a different sequence of events.
• Who was that in the photo you posted on Instagram? – You’re obviously going to be a bit jealous and suspicious but you have to understand that that’s your problem now, not theirs. Also, this sounds insecure and slightly sad, which is not a good position to be in with an ex.

• What can I do to convince you to come back? – This distinctly sounds like begging, which will generally strip you of all power in the situation. Not only will your ex immediately value you less, but they’ll also know that they just have to snap their fingers to get your attention back on them.

Should you really talk to your ex?

Not if you want to get over them quickly and healthily. Most therapists agree with a complete cut-off approach in the short term and that talking to an ex should only be done sporadically after that, until you feel like you’ve moved past the relationship. A University of Illinois study found that people who kept in contact with their exes struggled with severing their old emotional bonds to them, resulting in a longer and more psychologically painful healing process.⁷

In short, you can’t let go of something while still holding onto it. This sounds like the kind of basic logic one might want to explain to a newborn baby, and yet we as fully developed adults often make this exact mistake while wondering why our sense of well-being isn’t improving and we’re not meeting anyone new.

But we also understand that people are only human. It’s incredibly challenging just going cold turkey and cutting off all contact with someone who you deeply cared for or even perhaps loved forever. But even if you plan to get them back, pursuing that before you’ve even processed the breakup itself is not going to seem mature or healthy to them. Just give yourself time.

When should you stop talking to your ex?

We generally agree with the experts who say that a no contact rule is the healthiest way to process the grief of a recent breakup while reestablishing your independence and identity outside the relationship again. This means zero contact, even contact that’s one-sided. So, no texts, no calls, and no social media interaction (including checking their profiles).  

The length of a no-contact period differs between couples. The rule of thumb is 3 months. However, shorter, less intense relationships may only require a no-contact period of less than a month.  

This rule of thumb isn’t a guess, though. A study found that even when ending a very low-quality long-term relationship, most people only really begin to show improvement at the 3-month mark, with almost all respondents expressing a significant improvement to their sense of well-being and emotional healing after 6 months.⁸

If you’re within this general period of the break-up, you may think it’s safe to get in touch and start exploring those pressing questions you want to ask your ex. But ask yourself, do you actually feel better about the breakup? How often do you think of them? Are the emotions that the thoughts evoke suitably neutral? Are they finally outside the frame of your vision for your future? Be realistic and kind to yourself rather than give in to temptation.

This can be a somewhat delicate situation. Whether an ex cut off communication for understandable or seemingly irrational reasons, pushing them to talk can often cross a boundary. Empathetic caution is always a good approach.  

• Your first instinct will be that it’s because of something you did but unless you can specifically remember something egregious, they’re probably avoiding contact for their own reasons or they may still be angry about the breakup.
• Give them the space they want during this time, even if it is difficult. The more pressure they feel the less likely they’ll be to change their mind. This often happens with people who focus on “winning” the breakup instead of trying to grow from it.
• Focus on yourself during this time, practicing self-care and talking through your problems with someone you trust or even a professional.
• By working on improving yourself, you’ll find that not only do you think of them less but they will start showing increased interest in initiating contact themselves. 
• If you have some pressing questions to ask your ex or just want to vent certain things, put it all together in a letter. Take a day,read it again and then decide if you still want to send it. 
• If they still aren’t responsive after you’ve given them time and space, just let it go. Perhaps, one day, they‘ll come to you.

How to know if you’re still in love or just lonely?

This is a very important distinction to make before you make the decision to re-establish contact with an ex or pursue a reunion. Our pain and loneliness can often trick us into focusing mostly on the good times of a recently ended relationship, while omitting the bad.      

• When does the impulse to get back together strike you? At emotional high points or when you’re already feeling down or lonely? Our general mood can often color our reality in different ways, which is why you should only concern yourself with consistent desires.
• Consider if you got back together today, having changed all the problems they had with you. Would you be satisfied with them if they hadn’t changed at all?
• If you’re more bothered by the idea of them dating someone else than the idea of never getting back together, you’re likely still processing your emotions from the breakup. 
• Consider whether your communication patterns have changed. Do your conversations today feel different from how you used to relate to each other? If they do, your affection may be the result of seeing a noticeable difference in how you two functionally interact now.
• Do you want to go back to the way things were or do you think you’d actually be a better fit now that you’ve both matured since the breakup? Nostalgia is a great concept for keeping your memories alive and vibrant but it’s far from the objective truth.