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Top Five Biggest Regrets After A Breakup Or Divorce

Dr. Lisa Lawless

Dr. Lisa Lawless, CEO of Holistic Wisdom
Clinical Psychotherapist: Relationship & Sexual Health Expert

broken heart made with cookie dough

A Time To Reflect

When people go through a breakup, they often regret certain things they did or didn't do. They get stuck thinking about their regrets but do nothing to change them. Breakups are the ideal time to reflect because your past relationships that did not work out all have one thing in common. You.

Even if your partner was abusive and would have definitely qualified as the one at fault by a landslide on the Reddit forum "Am I the Asshole?" (AITA), you can still learn how to be a better partner; we all can. After all, we are all growing and evolving, as there is always room for improvement.

This article will review the five biggest regrets people have as they reflect on a split, how to learn from them, and what to do better going forward.

1) Not Communicating Well

If you regret not communicating well in past relationships, working on improving your communication skills is essential. It can be tricky when someone has pushed you to your limits, you are are stressed, or even too "hangry" to communicate well, but with education and practice, you can do it.

Now, I know what you're thinking, "But Dr. Lisa, how do I even begin to up my game and improve my communication skills?" Fear not, for there are a plethora of options at your disposal, and I shall reveal them to you!

For one, you could start by cracking open a good book. Ok, I know I just aged myself on that one. As a Gen Xer, I still think in terms of books, but they do still exist (for now), and there are good ones for enhancing communication skills.

However, you can also jump on the internet and Google some things; heck, you can even read more of my articles. After all, I spend an ungodly amount of time (I mean, ridiculously long and almost beyond human comprehension amount of time) on this site, providing resources and chatting up a storm about how to do just this very thing!

If reading isn't your thing, don't worry, there are other options. You could watch videos, listen to audiobooks, podcasts, or attend a workshop.

And if you really want to up your communication game, you could even consider visiting a therapist. Think of therapists as personal trainers for your emotional and mental workouts. And for those Gen X folks out there, think of it like therapy in the way that Hans and Franz on SNL used to say, "I want to Pump... you up!"

But if you're really looking for the best of the best, may I suggest listening to yours truly? I don't like to brag (okay, maybe just a little), but word on the street is that I'm pretty darn good at what I do. And who doesn't love learning from an expert who's both knowledgeable and entertaining? Well, at least my mom thinks so, or so she says.

2) Not Making The Relationship A Priority

If you regret not prioritizing your partner, it's essential to make sure you make time for your future relationships. Prioritizing your partner by showing affection and working on the relationship through intimacy-building is part of what successful couples do. So find time to dedicate to your partner for a good old-fashioned smooch fest or quality time to show them the love and attention they deserve.

Here are eight peachy keen tricks to give your communication an extra zing:

Be Considerate

Being considerate is a crucial ingredient in the communication recipe; no one likes a partner constantly interrupting or talking over them. I know this sounds easy and like a no-brainer, but I cannot tell you how mean, inconsiderate, and rude couples can be to one another, let alone the manipulative games people play. Practice the golden rule, and you will be golden. 

Actively Listen

For starters, try to really listen to what your partner is saying. I know it's a revolutionary concept, I say sarcastically, but trust me, most people don't do it! Pay attention to a partner's body language, the tone of voice, and the words they're using to help you understand where they're coming from and what they need from you.

Practice active listening by giving your full attention to people while they are speaking, maintaining eye contact, and asking questions to clarify what they are saying.

Be Open & Honest

Also, for the love of Pete, be open and honest. Don't shy away from difficult conversations, even if they make you uncomfortable. I can't tell you how often couples don't say what they really feel and think to one another in a loving manner and then have to go through some really painful experiences that were completely avoidable.

Use "I" Statements

Use "I" statements instead of "you" statements. For example, instead of saying, "You always do this and are driving me crazy," try saying, "I feel frustrated when this happens and I want to work with you to avoid that." This helps to avoid language that blames your partner and creates defensiveness. It also keeps the conversation more proactive and positive, and proactive and positive is what we want, it's good stuff.

Don't Forget Humor & Playfulness

Remember to inject a little humor into your conversations. Laughter truly is the best medicine, and it can do wonders for diffusing tense situations. So, if you and your partner share a humorous bond, you can try a playful approach when things get on your nerves.

However, before you go off cracking jokes and getting into mischief, it's important to remember that humor is not a one-size-fits-all solution. If your partner doesn't respond well to this kind of repartee, it's best to steer clear of doing it and definitely avoid it when your partner is really upset or hurt.

Assuming you have the right partner and dynamic, you could try saying something like, "You know, you're really pushing my buttons right now, but I love your crazy self, and I want to find better ways to handle this in the future."

The key is to say it with a light-hearted, upbeat tone and plenty of affection. After all, you're in this together, through thick and thin. So, if comedy is a big part of your relationship, sprinkle in some humor, and keep the love and laughter flowing!


Learn nonverbal cues such as body language, tone of voice, and facial expressions. In addition, pay attention to the natural rhythms and patterns of your partner's behavior in a relationship. These things can provide a contextual understanding of your partner's needs and mindset.


Practice empathy by putting yourself in the other person's shoes and seeing things from their perspective. Then verbalize this to your partner to build trust and understanding. The two most important things that any person wants to feel from a partner is to be appreciated and understood.

Let me repeat that for those in the back, the most important thing anyone wants to feel in a partnership is appreciated and understood.

Get Feedback

To improve, we need to be open to constructive criticism, so swallow your pride and ask your trusted friends, family, or even a counselor to give you some honest feedback. This can help you to identify areas where you can improve and continue to grow in your communication skills.

By identifying areas where you can improve, you're showing a proactive and empathetic approach to your communication skills. And hey, if all else fails, remember the wise words of comedian Steven Wright: "I'm not arguing; I'm just explaining why I'm right."

Go Forth My Friend

So there you have some super-duper handy tips for upping your communication game. Remember, a little effort goes a long way when prioritizing your relationship. Now go forth, be free, and communicate!

3) Cheating On Their Partner

If you regret cheating on your partner, it's vital to understand why you did it and address any unresolved issues. Taking responsibility for your actions, apologizing, and exploring what it means to have integrity and trust in a relationship are essential steps to healing.

Be bold and have those awkward yet oh-so-important conversations about boundaries and expectations. Yes, it may feel like you're trying to navigate a minefield with a blindfold, but trust me, it's worth it in the end.

To learn more, see our How & Why People Cheat Guide.

4) Not Being True To Themselves

If you regret not being true to yourself in past relationships, it can lead to a lack of intimacy and trust. It's important to explore why you felt inhibited and to use therapy or support systems to understand and celebrate your authentic self.

It's like wearing a mask all the time; eventually, you forget who you really are underneath it all. And that can make it hard for your partner to truly get to know you, trust you, and feel connected to you in a meaningful way. After all, you cannot know what it is to be loved by someone unless you are willing to let them love the real you.

5) Not Seeking Help

Seeking counseling can seem intimidating. You might think, "What if they judge me?" or "What if it doesn't even work?" But let me tell you something, neglecting to seek counseling is one of the most common regrets people have after a breakup. And that's not just my opinion; it's backed up by research.

And don't worry; we therapists won't judge you, not even for wearing socks with crocs. At least I won't. I like Crocs. There I said it; now you can judge me. I am comfortable with the ultimate vulnerability. 

Why People Don't Seek Help

So why do people hesitate to seek help? Well, there are a lot of reasons. Maybe you're feeling ashamed that your relationship didn't work out, or you're scared of being vulnerable and opening up to a stranger. Perhaps you just don't think it'll make a difference. But here's the thing, when it comes to navigating relationships, the support of others can be incredibly beneficial.

Avoid Crappy Therapists

Now, if I may speak candidly, there are a lot of crappy therapists, but there are many that are good, and out of those, you have to take time to find one that is right for you.

A therapist worth their salt can help you better understand things and provide you with tools to achieve your goals. They are also highly likely to enjoy wearing Crocs. That is a super good sign.

Therapy can be excellent, but finding the right therapist as well as the right type of therapy for you is key. Take your time finding the right therapist for you and if they do wear Crocs try not to judge them too hard, they are just trying to be comfortable and live their best lives.

If you tend to be in your head and over-analytical (like someone writing this article), you may want to consider therapies that get you in touch with a combined mental, emotional, and physical release, such as acupuncture, massage therapy, somatic therapy, dance/movement therapy, yoga therapy, art therapy, mindfulness-based therapies, and Gestalt therapy.

Some of these approaches involve more physically active experiences, which can be especially beneficial for individuals who are looking to engage with their bodies and minds in a more holistic way.

A Time To Grow

If you're experiencing any regrets after a breakup or divorce, take the time to reflect on your contributions of your separation and then focus on what you want in a future relationship. Then ask yourself what you need to work on to achieve your goals because you are in control of what happens next.

Having a clear vision of your goals and the work you need to achieve them will be vital for your personal growth and the potential for a healthy relationship in the future. I believe in you, you got this!

For more helpful information, please see our guide: Getting Over A Breakup & How Long It Takes.

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