How to Make Him Regret Losing You (11 Sneaky Ways)

Last updated on July 4, 2022 by April Maccario

Getting over a break-up, or running into an ex, is a mortifying experience for almost anyone. You don’t want to look bad; else, it’s a win for them. You have to look like you’re ‘winning the break-up.’

To feel better about the situation, you’ll need to know how to make him regret losing you. With tips from this article, you’ll get the best post-breakup experience to prepare you for an unexpected meetup with an ex.

These tips will further ensure you take control of your separation, and more importantly, it’ll help you bag that final win.

11 Ways to Make Him Regret Losing You

1. Set boundaries

One crucial way to make a man feel sorry for breaking up with you is by reminding him that he no longer has unrestricted access to you. Setting boundaries is vital after any separation. Your ex-boyfriend shouldn’t determine when to meet or how often you should talk.

If his terms force you to communicate more than you want, then express your discomfort to him. More importantly, the routines both of you had before the separation should be called off, and you should establish the no-contact rule for a minimum of one to two months. This will make him ruminate and possibly feel sorry for the separation.

2. Genuinely be happy

After no contact for a respective period, irrespective of how you’re coping with the separation, you owe it to yourself to appear happy and delighted whenever you see your ex-boyfriend. This shows you’re a thousand steps ahead of the break, and you’ve put him in the friend zone. 

If you look displeased, he’ll feel like he has a certain power over you. Relate with him casually, and don’t let your emotions seep through. This move will stir up jealousy in your ex; he’ll know that your vulnerable side is not accessible, and he can’t have you like before. In a nutshell, he’ll feel sorry that he lost you.

3. Fill him in

If you run into an ex, the best way to make him feel sorry for breaking up with you is to fill him in on how well you’ve been doing. Indeed, there has to be one outstanding experience since the separation. Use that information to your advantage. 

It could be something big like visiting an expensive resort overseas or something small like having healthier skin. The most important thing is that you’re doing well, and you’re not afraid to show it. You don’t necessarily have to tell him all these events happened after the separation. He will certainly know they did, and that’s a win for you.

4. Talk about career

There’s a high chance your ex will want to know about the state of your career since he’s been gone. In such a situation, you have to be tactical when answering. If you’ve got a new job, then that’s a plus for you. This fact would seamlessly make you look great to your ex. However, if you’re still working at the same place, talk about one amazing thing that happened there.

Your excitement about the situation will show you’re doing great. Let him know that things are looking good for you at your workplace. No, it’s not an avenue to get back at him, but a way to look like less of a mess. If you’re currently unemployed, there is no need to feel anxious either. Highlight your achievements and how you’re taking a break to live life and take great care of yourself.

5. Become a better you

become a better you

There’s no better revenge you can give to an ex than exclusively focusing on becoming a better version of yourself. If you pay too much attention to him, you’ll only discover new reasons to be hurt about the separation. On the contrary, making the post-breakup experience about you will help you move on faster than you imagined. 

Be fashionable, hit the gym, take an online course, start a business, and do anything you’ve always dreamt of doing. This part is more about you and not about trying to get your ex back.

At the end of the day, everyone, including your ex, will notice the positive changes around you. More importantly, you’d have done something profitable for yourself.

6. Talk about the good times

Talking about what you had with your ex might sound contradictory, but it works. One effective way to make him regret losing you is to reminisce about the good times you had together. This process will make him compare the past to the present and think about what he’s missing out with you. 

Similar to this, you can ask about mutual friends and perhaps some of his close buddies. This will make him remember how everything was before. Talk about these things in a light that clearly suggests you don’t want your ex back. Ultimately, that will make him feel sorry about severing the relationship a lot more than he expected. Altogether, he will see things in a new light.

7. Define your relationship with him

It’s easy for an ex to get over his head and become overly friendly with you. If you’ve used some of the tips listed above, he might begin to miss you and forget all about the boundaries you set up. 

This stage requires you to take things a little further and define the relationship. Make it clear that you’re strictly friends and that everything can’t be how it used to be. Preventing him from having access to you will make him feel sorry for losing you. He’ll reminisce on the perks of being in a relationship with you and would crave the old times.

8. Talk about your new relationship

Talking about your new partner might seem too on the nose, but you’ll be able to make your ex think about what he’s lost when it’s done correctly. The key is to create a comment about the man in your life amid a conversation. Don’t pause when you mention it, but keep on talking to avoid your ex realizing that you simply want him to know there’s someone else. 

You can say it casually concerning something he says. For example, if he’s talking about a new movie that came out recently, you can mention how you recently watched it with your boyfriend over the weekend. The fact that you’ve moved on will ignite a spark of jealousy in him.

9. Treat yourself

Genuinely enjoying yourself is something you owe yourself after a separation. Breaking up with someone you cared about hurts, but getting back on track is more important than anything else. 

Treat yourself to something special, and know that you’re worth it. Get a massage, buy your favorite meal, get that dress you’ve always wanted, and spoil yourself like a queen. This process will affect how you view the situation and will reflect in your interaction with others. 

If you eventually run into your ex, you will feel above and beyond, and won’t be intimidated by his presence. You’d have accomplished something psychologically, which he will perceive.

10. Talk more about your accomplishments

talk more about your accomplishments

It’s never a bad idea to talk about your good deeds to an ex. Have you bought a car recently? Moved into a new apartment? Have you got new furniture? Anything counts when it boils down to looking good in front of your ex. You can also include your little acts of kindness to remind your ex-boyfriend of the sweet person he lost. 

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Did you help an old lady cross the street? Give out your last cash to someone who needed it? Donated stuff to charity? He won’t be able to deny the fact that you’re living well without him and contributing to society while at it.

11. Be social

You’ll need help from other people if you plan to make your ex regret breaking up with you. Being social is the key to your liberty after a separation. Meet new people, go to new places, and have fun more often. 

Don’t be afraid to share the highlights of your adventure on social media because that’s the only way your ex will know you’re doing fine without them. Nonetheless, please don’t make your adventures all about your ex. Make sure you’re enjoying your new experiences; else, you’ll be hurt all over if you don’t get a reaction.


What makes a man regret losing you?

Moving on and living a fulfilled life without him will make an ex regret breaking up with you. If they’re reminded of how great things were, they’ll be hurt that they let you go.

How long does it take for a guy to regret losing you?

If the no-contact rule is established correctly, it should take a guy two to three weeks to feel sorry for breaking up with you. Keep your distance and refrain from contacting him in any way possible. 

How do you make someone regret hurting you?

If someone offends you and shows no remorse, the best thing to do is keep your distance, live freely, and live happily. Make them know they have no control over your emotions and build up boundaries even though they try to come back into your life.

How do you make a man miss you and want you back?

Becoming a better version of yourself is the best revenge after separation. Focus on self-development, making your life better, and being more successful. The more you move on from the break, the more he’ll miss you and want to get back together.

Does silence make a man miss you?

Silence is the best way to make a man miss you. After any separation, it’s essential to establish the no-contact rule for a minimum of one to two months. This process will give him ample time to ruminate and possibly want to get back to you.

In Conclusion

Did you enjoy this article? Remember not to focus solely on your ex. Try to make your life better in every way, and stay positive throughout the process. If you liked this article, kindly leave a comment below, and share it with others.

Do you hate it how everything seems to always revolve round him while you just seem to be an afterthought sometimes?
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It almost makes you wonder whether he actually likes you or whether he's just stringing you along.

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April Maccario
I'm a huge nerd when it comes to understanding how relationships between men and women work, and what drives a certain behavior. I spend much of my time getting into the nitty-gritty and try to share my findings on this site with the hope of making life a little easier for women that are struggling in their relationships or love life.

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