[Fridaykaye26]

I am 28 and my boyfriend is 24. I have been married and divorced, and he has only experienced high school love. I have had many relationships and flings, and he has not. I had a tough, unstable childhood; we were poor and moved once a year or more. He had a good upbringing; he was spoiled and grew up in the family home. I have a tremendous amount of understanding and experience, and he does not. I am teaching him. You see, it’s these differences that attract us to one another. We both want we never had and live it through one another. He despises his childhood as do I- we would like nothing more than to have had a childhood like the other has had.

We fight over my past and his inability to understand that I made mistakes. We go through spurts of honesty where I feel comfortable telling him details about things that happened five, six, seven, or eight years ago, and how I had learned from the mistake. He acts enthralled and understanding, but a few months down the road when we have an argument, he throws these things in my face. It’s like he loves AND hates me all at the same time. Is this possible?

We are having such communication issues that we are on the verge of breaking up. I love him so much and am willing to do whatever it takes to make it work. Suggestions?

[April Masini, your AskApril]

Yes, his loving and hating you at the same time makes sense, but what I think is really happening is that he’s conflicted. He loves things about you and he hates things about you, and he isn’t mature enough to process the fact that everyone has things about them that a lover or boyfriend or husband will love — and hate. To make a relationship work there has to be enough overlap in compatibility so that there is no instability. Because you’re familiar with instability in your own life, you need to make sure you don’t seek it out in your relationships. It sounds like by choosing this guy you’re doing exactly that — choosing someone who doesn’t have enough compatibility with your life to make things work in the long run.

Everyone comes to a relationship with baggage, but the trick to making it work, I always say, is to have [i]matching luggage. [/i] I’m not saying it can’t work, but relationships are a lot easier when there is mutual understanding in divorces, past relationships, children, etc. Differences are intriguing, but if there are too many and they are unresolved and constant sources of conflict, you’re looking at another break up down the line.

For example, imagine if you both spoke completely different languages, say, Portuguese and Farsi. And there was no common language. At first the differences would be charming and sexy and you’d find ways to communicate and make your dates work. Romance grows and the differences are still charming, but over time as you endure the stresses that every life and relationship goes through, those language differences are going to become wildly frustrating and the source of derivative anger because you just can’t communicate even though you’ve both learned some of each others’ languages. When the tension is highest, you both revert to your native languages and are frustrated that the other doesn’t speak your tongue.

Try to find someone who is more compatible with you from the start. There will always be differences, but it sounds like there are just too many for the two of you to bridge peacefully.

I hope that helps. Let me know how things go. And join me on Facebook. Here’s the link for AskApril.com on Facebook: [url][/url].

[Fridaykaye26]

Yes, April, your insight and advice make sense. It seems quite simple the way you put it, but I thought the worst, thought he was actually hating me! Indeed it is certain things about me that he cannot tolerate which brings us to another issue we’ve been having.

In the past, at the begining of our relationship, I did some things that he interpreted as sneaky and wrong that need be forgiven. I once told him (in an effort to be truthful) about a flirty conversation I had a bar, lasting no more than five minutes. In addition to that but well after, I received an email out-of-the-blue from a guy I had dated briefly. When we dated I was totally out of control, had a substance abuse problem, and had a dead end job with no aspirations. Since then I was totally sober and clean, gotten my life together, enrolled back in school, and was in-love with my boyfriend. I was proud of the change in me and wanted to communicate this with one who knew me as I was before, so I replied back. It was harmless and I did not delete the email afterwards in another effort to be truthful. But when my boyfriend came across it, my plan back-fired and he interpreted the message as yet another sneaky and wrong thing.

These events happened well over a year ago, but he still brings them up every single time we argue. He says I’m forgiven them, but still brings them up adversly! I believed that he hadn’t truely forgiven me and was intentionally torturing me, but a friend of mine told me that he is doing this because he has no valid defense for the things we argue over, so he is deflecting blame back on me. Of course it’s no surprise that anytime he messes up and knows he was wrong, he points the finger back at me. Truth is- I like my friends idea better than mine=)

Going back to the advice you previously gave me, I have tried dating men that were of closer compatability such as men who had much of the same experience I’ve had and men with similar backgrounds/childhoods. These past relationships DID NOT WORK and only caused me to take steps backwards. I was a miserable, lost individual finding other miserable, lost men to accompany me. My experiences with them got me nowhere, only allowed me to appreciate the goodness in my current boyfriend. He is so good to me in so many ways which is why I’m here, discussing our issues, asking advice, and searching for answers to hold onto him.

[April Masini, your AskApril]

It sounds like you’re the one who goes back and forth as well as he does. 😕 First you say he’s wonderful, but then you say he brings up guys you flirted with an entire year ago over and over again. You are aware of the maturity problem between the two of you but you seem very stubborn about not wanting to date other men because you haven’t met Mr. Right just yet. In your own words, you were [quote]…a miserable, lost individual finding other miserable, lost men to accompany me. My experiences with them got me nowhere…[/quote]

Well, if you were miserable of course those men you were going to pull in were going to be miserable, too. 🙁

The trick is to make sure you are healthy and open minded and then you’ll attract other healthy and open minded people into your life. If you can’t tell your boyfriend about your past without him throwing those events back in your face, as you put it, with judgment and anger, I don’t think he’s ready for the big issues in life that can challenge any relationship.

If there’s anything else you need help with, I’m happy to do so. I’m not sure this is what you want to hear, but I’m sure you know I’ll tell you the truth when no one else will! 😉

Join me on Facebook. I’d love to see you there. Here’s that link: [url][/url].

[Fridaykaye26]

You are right. I am stubborn. I don’t want to believe that this (us) just won’t work. Thanks.

[Fridaykaye26]

Maybe it’s that I’m trying to understand why it won’t work. What about the previous situation- do you think it’s a forgiveness thing or a defense thing?

[April Masini, your AskApril]

Please clarify what “previous situation” you’re talking about. If you are clear I can give you better advice! 😀

[Fridaykaye26]

Sorry, the situation I described above: He says I’m forgiven for things I’ve done one or two years ago, but when we have an argument because of something he’s done, he continously brings up the events I’m supposedly forgiven of.

Could it be that he really hasn’t forgiven me? Or that he has no valid defense for what he’s done so his only defense is to deflect blame back on me.

[April Masini, your AskApril]

I think that it’s the former. He brings up things he says he’s forgiven you for, in the heat of an argument, because the truth is he hasn’t let those things go completely. But that’s not the big problem here, and I hope you won’t distract yourself with derivative issues. The bigger problem looms. 😕

I hope you’ll join me on Facebook!! Here’s that link: [url][/url]

[Ethan Morales]

The dynamic you’re describing him loving and hating you at the same time isn’t unusual, but it’s less about true “love-hate” and more about emotional immaturity and conflict. He admires you, but he also struggles with processing your past and the realities of your experiences. Instead of integrating those facts into his understanding of you, he weaponizes them during arguments. That’s not a reflection on you being “bad” or wrong; it’s about him not being equipped emotionally to handle a partner with a complex history.

You clearly bring experience, perspective, and understanding into the relationship, while he is still learning about adult relationships and emotional nuance. That imbalance can be exciting at first the attraction to differences but over time, it creates instability. Mutual growth is important, but it has to be reciprocal, not one-sided teaching or guiding. Otherwise, resentment builds on both sides.

April’s “matching luggage” analogy is spot-on. Compatibility isn’t just about chemistry or attraction; it’s about being able to navigate stress, differences, and disagreements without constantly reopening old wounds. If the communication patterns you have now arguments about your past, feelings of being misunderstood are recurring, they’re likely to intensify, not resolve, over time.

While love and attraction are real, the relationship may be unsustainable unless both of you develop stronger emotional maturity and mutual understanding. You’re already aware of the tension and instability, which is a red flag. Protecting your emotional health and seeking a partner who can communicate, process past baggage respectfully, and handle conflict without bringing up hurtful history may serve you better in the long run. Right now, this relationship seems to demand more energy to “teach” than to simply grow together. differences can be intriguing, but unresolved ones that regularly spark conflict are a warning sign, not a challenge to overcome.

[Tara]

This relationship is lopsided, immature, and slowly burning itself to the ground, and you’re acting shocked while holding the match.
You’re 28, divorced, experienced, and have lived an adult life. He’s 24 with a high-school level emotional toolkit and zero relationship mileage. You keep calling it “teaching him,” as if you’re mentoring some wide-eyed intern. What you’re actually doing is parenting your boyfriend and mistaking that power imbalance for compatibility.

Here’s the ugly part you don’t want to admit: he can’t handle your past because he’s not emotionally built for a partner who had a life before him. He’s not mature enough to process your experiences, so he stores them up like ammo and fires them at you whenever he feels insecure. That’s not love. That’s immaturity with a jealousy problem.

You keep opening up, hoping he’ll rise to your level, and he keeps proving he won’t. If a man takes the private things you confess in vulnerability and uses them as weapons, he doesn’t love you, “and hate you at the same time.” He just doesn’t respect you. And you’re letting him.

You want to “do whatever it takes”? Here’s what it takes: stop lowering yourself to fit into a relationship with someone who isn’t ready for you. Stop confusing emotional labor with love. Stop trying to turn a boy into the partner you wish he could be. He’s four years younger chronologically and about ten years behind you emotionally. That gap isn’t closing.

[Sally]

He loves the parts of you that feel steady and experienced, but he also gets scared of them. And because he hasn’t lived as much life yet, your past feels bigger to him than it should. That’s not your fault that’s just where he is.

What worries me is how he uses your honesty against you later. That’s not maturity, that’s insecurity talking. And it’s hard to build anything solid when your past becomes ammunition every time there’s a fight.

You can’t teach him his way into being your equal. He has to grow into that on his own.

If you want this to work, the two of you need one calm conversation about what’s actually happening not the fights, not the stories, but the fear underneath it. And he has to meet you halfway. You can’t carry both sides.

[Natalie Noah]

It’s important to recognize that what you’re experiencing with your boyfriend is less about malicious intent on his part and more about emotional immaturity and unresolved baggage. His behavior loving and appreciating you in some moments, then throwing past events in your face during arguments signals that he hasn’t fully processed his feelings or learned how to handle conflict in a healthy way. While it’s normal for couples to struggle with past mistakes, repeatedly bringing them up shows that forgiveness hasn’t truly occurred on his side, or that he lacks the emotional tools to move past it. That’s not your fault, and it’s not a reflection of your worth.

Your own self-awareness is remarkable. You clearly understand that there’s a dynamic of “matching luggage” that is essential in relationships. You’ve acknowledged your own past struggles and the growth you’ve achieved, and you’ve realized that dating people with similar backgrounds to your former self didn’t serve you well. This shows maturity: you are seeking a partner who complements your life and growth, rather than one who mirrors chaos or instability. That’s an important distinction because it reflects that you’re ready to make conscious choices about who you allow in your life emotionally.

The conflict between your desire to hold onto him and the clear signals of his limitations is at the heart of this struggle. You love him, and that love is real, but love alone isn’t enough to sustain a relationship if there’s a recurring cycle of judgment, defensiveness, and emotional inconsistency. His actions especially bringing up old mistakes repeatedly show that he might not yet be capable of fully trusting, understanding, or partnering with you in a mature, balanced way. While you might feel like you need to fix or teach him, the truth is that his ability to process and act differently is ultimately his responsibility.

Your insistence on staying despite these red flags is understandable because of your attachment and investment, but it’s also a moment to reflect on your long-term emotional health. Relationships thrive on mutual respect, growth, and support, not cycles of judgment and defensiveness. You’ve done the work to grow and mature now it’s about assessing whether the person you’re with can truly meet you at that level. If the answer is no, loving yourself may mean creating space to allow him, or you both, to develop further individually before a healthy relationship is possible.

The big takeaway here is that while love and attraction can be intense, they cannot replace compatibility and emotional readiness. You are clearly aware of both your needs and his limitations, and that insight is your guide. The sooner you recognize whether his emotional maturity and your expectations can coexist peacefully, the better for your own growth and happiness. Sometimes, holding onto someone who can’t fully meet you in the present only delays your opportunity to experience the healthy, respectful love you deserve.

[Serena Vale]

Honestly… he hasn’t fully forgiven you. If he had, he wouldn’t keep pulling those old things out every time you two argue. That’s not forgiveness, that’s holding onto something and using it when he feels insecure or cornered.

But this isn’t just about the past.
It’s about the two of you being in very different places emotionally.

You’ve lived more life. You’ve made mistakes, grown, learned.
He hasn’t had that same experience, so when he feels hurt, he reacts in a more immature way, by throwing old things at you instead of talking about what’s actually wrong.

It doesn’t mean he hates you.
It means he doesn’t know how to handle certain feelings yet.

And that’s why your arguments feel so draining, you’re doing the emotional work for both of you.

Can it work? Maybe.
But only if he grows up emotionally and learns to let the past stay in the past.

You can’t fix this by explaining your past again or trying harder.
He has to work on how he communicates, how he forgives, and how he deals with conflict.

If you want, I can help you figure out how to bring this up to him in a calm, clear way.

[Serena Vale]

It honestly sounds like you two love each other, but you’re not meeting each other at the same emotional level. You’ve lived more life, made mistakes, learned from them. He hasn’t, so he doesn’t know how to handle your past without feeling threatened by it.

When someone keeps bringing up things they say they forgave, it usually means they didn’t actually let it go. He’s holding onto it because he doesn’t know how to deal with his own insecurities. So yes, it’s more about him than you.

But the bigger issue is this: you can’t build a steady future with someone who uses your past as ammo every time they’re hurt. That’s not communication, that’s immaturity.

You can love someone deeply and still not be able to build something healthy with them. And honestly, that’s the part that hurts the most.

If you stay, he has to grow up emotionally, learn how to communicate without weaponizing what you trusted him with. If he can’t do that, you’ll keep running in circles.

Love isn’t the problem here. Emotional readiness is.

If you want, I can help you phrase something to tell him directly.

[Member]

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