Questions You Need To Ask Your Boyfriend About His Ex

Dating experience | | , Sustainability Analyst & Content Writer
Updated On: May 4, 2024
serious questions to ask your boyfriend about his ex
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Getting into a new relationship can be a roller coaster ride. You find yourself falling in love with this person and you want to know everything about them. Understandably, you can’t help but be curious about their past. Figuring out what questions to ask your boyfriend about his ex without coming off as jealous is important. You don’t want him to feel like you’re grilling him about his life before you met him. 

You’ve probably already scoured all his social media, looking to get your hands on all the information you can get. God forbid, you see a photo of him with a former paramour. Sound the alarm bells, this curiosity isn’t going anywhere unless you get the answers you’re looking for.

Apart from the “So, what are we?” queries, serious questions to ask your boyfriend include questions about his past lovers. There’s a thirst to know about his exes and past dynamics that you just can’t shake off. If you’re wondering whether it’s okay to ask your boyfriend about his ex, let’s answer all your questions and talk about all you need to ask him.

Is It Okay To Ask Your Boyfriend About His Ex?

It is fair to want to know about your partner’s past. Being curious is definitely not a crime. Discussing your exes and previous relationships, as well as your heartbreaks and struggles, is all part of getting to know each other better and forming stronger bonds.

Especially if you look at this relationship as a long-term one, it’s good to know these things about your partner. For instance, what if he cheated in every relationship he’s ever been in? It doesn’t necessarily mean he’s going to do it again, but it’s always good to know what he has struggled with before he got into a relationship with you.

The questions to ask a guy about his past relationships will make you understand him a little bit more. Does he have an avoidant attachment style? Did his past relationships struggle because of recurring patterns or sporadic events? The more you understand the kind of person he is, the more you’ll be able to empathize when he’s portraying conflicting behavior.

However, it is never okay to fall prey to your insecurities and become a jealous girlfriend. You shouldn’t nag your partner for every single detail about his past relationships. It reflects very poorly on you and will make your boyfriend start having second thoughts about dating you for sure. Don’t worry, we are here to help you. Here are a few questions to ask your boyfriend about his ex without sounding nosy or inappropriate.

Related Reading: 5 brutally honest truths about long-term committed relationships

10 Questions To Ask Your Boyfriend About His Ex

Boyfriend Stories

Now that you know it’s absolutely okay to inquire about his past, the next logical question then becomes “What are some serious questions to ask your boyfriend?” No, asking him whether he’d still love you if you were a dog doesn’t qualify as a serious question. Although, who wouldn’t love a dog version of you? Adorable.

It is always a battle to figure out what questions to ask your boyfriend about his past without sounding jealous or too inquisitive. Talking to a boyfriend about his ex is no easy feat. You don’t want him to go “Oh god, here we go again” every time you bring the subject up. That’s why not only are the questions important but also how to ask him about his past relationships.

It takes a lot of courage and involves a fair bit of second-guessing. “What if he gets annoyed and storms off?”, “What if he calls his ex because he starts missing her again?”, and worst of all, “What if he blocks me?!” We understand that feeling and, therefore, we present to you a list of questions to ask your boyfriend about his ex that are completely appropriate.

1. How many past relationships have you had?

This is one of the most important questions to ask your boyfriend about his ex/exes. It’s totally justified to know how many relationships your new beau has been in. Are you dating a player? Or has he been a one-woman man up until now? Neither is really better than the other if you’d ask us.

If you are looking to be with him in the long run, you need to know if he can commit himself to you completely. The frequency and time span of his past relationships will give you a good idea of this. 

2. How did you meet your ex?

How a person met their ex can tell you a lot about them and their old relationship. For example, did they meet at a party, at a coffee shop, online, or through some friends? If they met through friends, they could still be a part of a common friend circle. It’s always best to know if this is the case so you can prepare yourself to possibly meet his ex at get-togethers with his friends.

If they met under the most dreamy circumstances, however, don’t start comparing and be sad that you met him through a dating app. If you ask us, how two people meet is overplayed. What matters most is what you two do after you meet. And with the help of these questions to ask a guy about his past relationships, you’ll be able to make sure what you do after the meeting is always smooth sailing.

3. Are you in touch with your ex? What’s your equation like?

Can exes really be friends? It’s a question that’s been bothering humankind since we started communicating, we’d say. There’s no reason for caveman John to be talking to cavewoman Alex after they break up. Get back to figuring out how to make a fire, John.

It’s always best to be aware when it comes to friends-with-exes territory. We believe that if your boyfriend is indeed friends with his ex/exes, it’s good to find out early so you can prepare yourself. Though you may be convinced it’s a red flag, it’s entirely possible that there’s nothing wrong with being friends with your ex. Especially if they were friends before their relationship started.

If they are good friends, it is your responsibility as the partner to make a place in your heart for the ex and not be the jealous girlfriend. Yes, we know, it’s difficult and you’re never really not going to judge Alex when she’s eyeing your man, but try to control the urge to grapple at her just because she said “Looking good!” to your beau.

4. Why did you break up?

This is definitely one of the most important questions to ask your boyfriend about his ex. This question will tell you what is a total deal-breaker for your boyfriend. 

Ask him about what went wrong and why they drifted apart. What he wishes his ex hadn’t done. Something that might have hurt him deeply. It is good to know these aspects of your boyfriend’s life so you can stay clear of making the same mistakes their exes did.

If his answer is along the lines of “She was always trying to invade my personal space, I never appreciated that,” maybe reconsider asking him questions about the future while he’s playing video games.

5. How serious was the relationship?

How serious was the relationship

The seriousness of a past relationship is of much consequence to the current one. Did they just spend a few fleeting months together or did they go so far as to actually live together? This is an important question since if the relationship was serious, the ex was an important person in your boyfriend’s life.

When you’re looking for serious questions to ask your boyfriend, this one should top the list. If it was a serious one, what caused the breakup? How long ago was it? Are you just a replica of his ex? Okay, calm down, don’t give yourself an existential crisis with that last question. Talk it out with your beau, you’ll get all the answers you’re looking for.

6. Did you introduce your ex to your parents?

As far as serious relationships go, there are two levels; meeting-the-friends-serious level and then there is introducing-them-to-your-parents-serious level.

Needless to say, these are two very different levels. If they did introduce the ex to their parents, it means that somewhere in their mind they might have had plans to marry them. Even if they did, it might not necessarily mean they are still hung up on their ex if they broke up with them a long time ago. However, if it was a more recent matter, you might want to keep an eye out. 

Related Reading: Why you should be friends with your ex!

7. How long ago did you break up?

This question lets you know whether your boyfriend is actually ready for a new, serious, committed relationship. If he just got out of a serious relationship only a month ago, he could still be hung up on his ex and you could simply be a rebound. No one likes being a rebound and you do not want to end up in that position.

If you’re wondering about when to ask about past relationships, get this question out of the way as soon as you can. If he broke up with his former paramour just a few weeks ago, it usually isn’t too great a sign.

8. Are you sure you’re over your ex?

Now, we know this might sound a tad bit insecure, but better safe than sorry, right? Especially if the gap between the two relationships isn’t too long. If he is indeed over his ex, he will reassure you that he is and then you have nothing to worry about.

And in case he’s not over his ex, at least you will know at an earlier stage and can get out of the relationship sooner than later. Encourage him to be honest, you don’t want him to lie to you only to find him stalking his ex’s Instagram page.

9. What is the most fun date you went on with your ex?

This is one of the more light-hearted questions to ask your boyfriend about his ex. You can also ask them about the best present they ever got from their ex.

Questions like these will help you know his likes and dislikes and will give you the opportunity to top the best date he’s ever had. Did his ex get him a sweater he really liked? Pfft, what an amateur. Do one better by getting him that Rolex he can’t stop eyeing. He’ll forget all about his ex the minute you walk in with the best present ever.

See that? The questions to ask about past relationships are already helping you out. Who knew asking about his ex would end up making your dynamic a lot better?

Related Reading: 21 Serious Relationship Questions To Know Where You Stand

10. Do you still follow each other on social media?

We can’t deny that in this day and age, social media is a very important part of all our lives. In most cases, couples tend to unfollow each other on social media after a breakup. Unless they broke up on very cordial terms. Let’s be honest, do those breakups even exist, though?

Especially if you feel like you’re a rebound, this could be something to watch out for. However, if your boyfriend is still on good terms with his ex, this might not be that big a deal.

How Do I Talk To My Boyfriend About His Ex?

Now that you know the safe questions to ask your boyfriend about his ex, you should also know the correct way to broach the topic and the dos and don’ts of talking to your boyfriend about his ex.

  • Don’t make it a big deal: Approach the topic at hand in a very matter-of-fact manner and don’t make it sound like a big deal. The more serious you sound, the bigger of a deal it becomes
  • Keep jealousy at bay: Do not sound jealous. It is very important that you come from a place of curiosity and care more than jealousy while talking to your boyfriend about his ex
  • Don’t nag him with questions: Make sure you don’t hound him with these questions all at once but ask him in parts on different occasions. Do NOT nag him as this will make it seem like you’re suspicious and do not trust him. 
  • Be prepared to hear him out: Only ask your boyfriend these questions if you think you are prepared to hear the answers. If you feel like this topic will just make you upset, don’t broach the subject
  • Keep a good-spirited attitude: Take his answers in good spirit and know that you are his girlfriend now and have no need to be insecure, especially if you know he loves you
  • Be mindful of his mood: Make sure you judge his mood and then start with the serious questions to ask your boyfriend. Don’t catch him at a bad time
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Don’t beat yourself up about wanting to know about your boyfriend’s past relationships. It is human nature to want to know more about the people we love or are close to. If he loves you and has nothing to hide, he will be happy to share things about his past relationships with you and you will know you have found your match.

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