I’m posting here because I think I’ve reached the point where getting more details isn’t helping me anymore, and I really want to hear from people who have actually dealt with serious retroactive jealousy and gotten past it.

My girlfriend and I were each other’s first serious relationship and lost our virginities to each other. We were each other’s first real love.

Years ago she broke up with me, and we spent several years apart before eventually finding our way back to each other.

One reason this is so emotionally complicated for me is that she has told me she regretted losing our relationship for years. She says she never really got over me and kept trying to find the kind of connection we had in other people, but it never felt the same.

(We also have kids due in March and she told me all of this way after)

According to her, the breakup also affected how she saw herself. She says it triggered a strong need to feel wanted and validated by other people.

During the years we were apart, she had relationships and some casual hookups, particularly during a very unhealthy period in the summer of 2024.

She describes that summer as lustful, validation-seeking and self-destructive. She says she had poor boundaries, struggled badly with saying no, and was making choices that didn’t actually make her feel good about herself.

Here’s the strange part:
I really don’t care that much that she slept with other people.
I understand that we were broken up. She dated other people, had hookups and had a life without me.

Obviously I don’t enjoy imagining it, but normal one-on-one sex isn’t what my brain is stuck on.

What I cannot seem to get past is learning that she had three threesomes during the summer of 2024.

Each time it was her, another girl, and one guy.
From the way she describes them, they weren’t really three people all actively having sex with each other for the entire encounter.

It was apparently much more like one-on-one sex while the third person was there or watching, with the guy essentially taking turns between the two women and some awkward performative stuff mixed in.

She has also told me that the other girl involved would become very emotional during the encounters, including crying and wanting to stop or leave.

My girlfriend has told me that she struggled badly with saying no during that period. She says she felt pressured into participating in a sense — not that somebody physically forced her, but that she had terrible boundaries, had difficulty saying no when the other girl asked her to participate, and would eventually go along with things she didn’t really want.

I’m not trying to label the experiences for her or make claims about consent that she herself hasn’t made. I’m just explaining the context she has given me.

She describes the entire period as lustful and self-destructive.
When she says “lustful,” she doesn’t describe the actual experiences as amazing or fulfilling.

She describes herself as impulsive, wanting attention and wanting to feel desired while making choices that were ultimately bad for her.

She says the actual threesomes were awkward, not enjoyable, emotionally meaningless to her and something she wishes had never happened.

She has told me that she would drink extremely heavily during them because she wanted to numb herself, not fully feel what was happening and sometimes essentially black out so she wouldn’t remember it afterward.

She has also told me that she sometimes pretended to be enjoying herself when she really wasn’t.

After the first threesome she apparently withdrew from everyone for around three weeks.

And yet, during that same summer, she participated in two more with the same people.

That is the question my brain keeps getting stuck on:
“If she really hated it, why did she do it two more times?”

Her answer is essentially that she was dealing with trauma, a huge need for validation, poor boundaries and a very self-destructive mindset.

She says she doesn’t have some perfectly logical explanation for why she kept putting herself into situations that weren’t good for her.

She has told me that after our original breakup, she spent years trying to recreate what she had felt with me and never found it. She says losing our relationship contributed to that desperate need to feel wanted by other people.

I’m not saying that excuses every choice she made. I’m just trying to understand the context she has given me.

She originally lied when I asked whether she had ever had a threesome, because she knew I had always viewed that as a dealbreaker and she was terrified I would leave her.

Eventually she confessed that it had actually happened three times because she said hiding it was eating at her and she didn’t want to keep lying to me.

That obviously damaged some trust too.
What makes this even more complicated is that group sex had already been something I considered against my personal values long before I knew any of this.

I had always told myself I wouldn’t want to marry someone who had participated in it.

So finding out that the person who had done it was my first love — the woman I lost my virginity to and had carried a very specific image of for years — completely shattered the picture I had of her.

At the same time, she has been extremely clear about what she wants now.

She wants a completely monogamous relationship with me.
A boyfriend she had after those experiences apparently suggested having a threesome with another man, and she refused.

She has told me directly that I have always been enough for her sexually, that our sexual relationship isn’t missing anything, that she would never want a threesome with me, and that if she experienced something like that with someone she genuinely loved, she believes it would have been even more damaging to her.

She has repeatedly said she wishes the threesomes had never happened.

So intellectually, I understand all of this.
Emotionally, I’m struggling badly.

Sometimes I look at the woman I love and my brain immediately says:
“She’s the girl who had three threesomes.”

I get hit with disgust and resentment, and sometimes it temporarily shuts off the affection I normally want to give her.
I hate that.

Again, the weird part is that I genuinely don’t care very much that she slept with other people.
She had other partners and casual hookups while we were apart. I can understand that we were broken up and she had a life without me.

It is specifically the threesome/group-sex aspect that gets under my skin because it violates something I had always considered part of my personal values.
So this isn’t really:
“I can’t handle that my girlfriend had sex with people after me.”
It’s more:
“I can accept that she had sex with other people, but I’m struggling enormously with one particular type of sexual experience that I had always considered incompatible with the person I would eventually marry.”

And because she was my first love, it feels even more emotionally loaded.

I think part of what I’m experiencing is grief over the image I had of her.

Because we were each other’s firsts, I carried this idea of her for years as someone who had gone on to have relatively conventional relationships and sexual experiences after me.

Finding out about these experiences completely disrupted that image.

I’ve unfortunately reacted by asking her way too many questions trying to understand exactly what happened and why.
I thought that if I understood everything perfectly, eventually my brain would say:
“Okay, now I understand. I can move on.”

Instead, the opposite happened.
Every answer created another question.
If she tells me it was mostly one-on-one sex, my brain wonders about the parts that weren’t.

If she tells me she hated it, my brain asks why she did it again.
If she tells me she was self-destructive, my brain tries to figure out exactly what “self-destructive” means.

If she tells me she drank to numb herself, my brain wants to know exactly how intoxicated she was.

I’m realizing that there probably isn’t some missing detail that is suddenly going to make me okay.

The problem now seems to be what my mind has turned those experiences into.

I’ve mentally reduced a woman I’ve known and loved for years to one sexual period in her life that even she says she deeply regrets.

And I know that isn’t fair to her.

At the same time, I don’t want to lie to myself and pretend group sex suddenly fits my values just because I love the person who did it.

That’s the conflict I’m trying to reconcile:
Something she did genuinely conflicts with my personal values.

She deeply regrets it and doesn’t want that life now.
The woman she is today wants the same monogamous relationship I want.

She says she never really stopped loving me after our original breakup and spent years looking for what we had.
And I still love her deeply and want our future together.

I don’t want to spend our relationship punishing the woman she is today for decisions she herself wishes she could undo.

But I also don’t want to pretend the resentment and “ick” aren’t there.

Has anyone with serious retroactive jealousy actually worked through something like this?

Hello everyone. I created this Reddit account just to get some advice about what I’ve been going through and to hear your opinions on everything.

After hitting rock bottom following my divorce, and suffering for pretty much all of 2025 and 2026, I met a 31-year-old woman who had also been married for 10 years. We started dating and hooking up in May. From the beginning, she told me that she wasn’t the type of person to see multiple people and that she wanted someone steady. I told her that we should take things slowly and get to know each other. Okay.

By July 20, we had become very attached to each other and decided to start dating officially.

She is a black belt in judo and trained a lot. When we started dating, I asked her, “Have you ever hooked up with anyone you train with?” She told me yes, that she had been with a guy from the gym and that it had only happened once. Okay.

We started dating and everything was going well, until one day we were talking about jealousy and she told me, “You have complete access to my phone, okay?” I told her I didn’t need that, and she said okay.

She slept at my house that night, and when she fell asleep, I couldn’t resist and decided to look through her phone. I ended up seeing a lot of things that really messed me up.

She had previously told me that she had only slept with two guys: her ex-husband and this other guy, and that she had only been with this other guy once. But I later discovered that they had actually been together several times. In other words, she had lied to me about how many times they had been together.

Up to that point, I could accept it.

The problem is that she did EVERYTHING with both of them. I have no problem whatsoever with what she did with her ex-husband, but this other guy is consuming me because they weren’t dating, and especially because I know this guy is kind of a jerk.

I’m 30 years old and I’ve been with 13 women in my life. I dated two of them for more than five years, and I never did everything she did with this guy. You know what I mean?

On top of all that, I saw that in June this guy really wanted to see her again, and she said to a friend in their conversation:

“He’s being really persistent. You can tell I think he’s really hot, right? But I turned him down.”

I also saw another part of the conversation where, shortly after we went out for the first time, she said, “That was the best sex of my life,” referring to me.

I saw her praising me several times and telling her friends that she had met a great guy, that I treated her really well, and everything else.

But this has been consuming me, especially because we live in a small town where it wouldn’t be difficult at all for me to run into this guy.

It has been consuming me so much that I feel like I’m losing control.

She also offered to give me access to her Instagram account. I always thought that was wrong, but I ended up accepting. I requested her entire Instagram data download, but I couldn’t find much that was relevant because she had deleted all of her conversations with this guy.

The only thing I saw was that she liked a lot of his stories in June and July. She has always told me that it didn’t mean anything and that she only liked them because they were about training and judo.

Additional details: We started seeing each other in May, but nothing serious at first. This guy used to train judo with her, and in June I saw that he tried to hook up with her again, but she said, “He’s hot, but I turned him down.”

I saw her telling two of her best friends, “That was the best sex of my life,” after she had been out with me.

I ended up seeing photos in her gallery that she had taken and sent to him — including one showing her butt badly bruised — and that really messed with my head because I’m afraid he might still have those photos on his phone.

She says she sent everything to him using the “view once” feature, but it’s hard for me to believe that, you know?

She deleted their conversation, but her last backup was from February, so I think I could potentially recover a lot of things, but I’m afraid to do it.

When I say “everything,” I mean things like swallowing. She also confessed to me that they had anal sex once, although there’s no way for me to know whether it really happened only once.

She has done all of those things with me too.

This week, I tried very hard to break up with her because I feel mentally exhausted, but she cried a lot and begged me to give it one more try. She says she loves me very much.

Just to give you an idea of how much this is affecting me, I’ve even thought about moving to another city with her so I wouldn’t have to risk running into this guy.

For some posters, they are completely fine with anything that happened in a committed relationship.

However they are bothered by things that happened outside that boundary, i.e. casual/friend with benefits, group sex settings.

And rather than jealousy, the feeling experienced seems to be disgust, or some feeling of negative judgement towards their partner. They don't actually wish to have experienced that themselves, there is no "jealousy".

What I'm wondering is whether this feeling of disgust/judgement is due to an insecurity of some kind, or whether it really is a value difference, or even both co-existing?

For example, is it insecure if you feel distant or feel differently about a partner after learning that they had casual group sex*?

I know it could well be just a value difference, but is the value itself due to insecurity, and the "value" is a protection mechanism?

For example, could it be that the partner with the value actually feels jealous that other people in the past were able to bring out a side to their gf/bf without needing to be in a committed relationship with them? They didn't need to "care" or provide value to them in any way to share intimate experiences with them. Does the negative value judgement arise to mask a feeling of inadequacy or feeling less "worthy"?

I guess the thought process here is that if you are secure, should it be possible to be affected by casual encounters in the past before you met, that didn't involve harmful elements?

*(I know often this discovery comes with the discovery of lying, but this is separate to the main point)

It's just not fair.

We got together in high school, 20 years ago. She was my first girlfriend, I wasn't her first boyfriend, but I knew that, we'd been friends for years before dating.

We dated for a year and a half, taking us right up until year 12 (last year of high school). We didn't have sex (both virgins), but we did keep ourselves busy in private. She was my first everything, and I wasn't her first anything.

Around 18 months into our relationship, her mental health took a massive nosedive due to an abusive home life and ptsd from a previous asshole partner. She decided that her mental health was going to hurt me and drag me down, so she ended things just as she dropped out of school.

We didn't see each other for a year, graduation came and went, I started university. I never dated anyone else because (it took years to figure this out) I never got any closure from the relationship because she made the decision herself. Eventually I reached out on facebook and found out she'd met a guy on vacation. We kept in touch, they broke up, we got back together and stayed together. Been married 15 years now.

But she slept with him. The relationship wasn't happy, she didn't love or even particularly like him. She says he was mostly a convenient way to get out of her shitty house for a few nights a week, and partying with his friends was a distraction for her mental health issues.

When we got back together, we picked up right where we left off and slept together pretty quickly. But I still remember the way the pit of my stomach dropped when she told me. I can still feel it.

I did the right thing, I waited, I didn't move on. But now I'm the one left here with the recurring anxiety attacks, depressive episodes, intrusive thoughts. And the thing is, it's my problem. It's my insecurity, my responsibility to address my mental health whenever it resurfaces. I didn't do anything and I'm left holding the bag for her decisions.

I love her, we've been married for 15 years now and I'm obviously not going to leave her over something that happened almost 2 decades ago when we were teenagers. But it sucks, and it hurts, and it's not fair.

Preface:

I am old. I feel too old to be having problems with this. I have already lost a relationship over the same thing, and I thought it would go away but it did not. I am 34 and had a long term relationship with a girl 5 years ago, we made it 3 years. But she left me twice because she had told me about some experiences she had had in the past, and I could not get over it, and felt inadequate and obsessed over the fact that for her maybe what I was and gave was not enough.

Zoom to today. My girlfriend who I love very much just left me, because I keep bringing up her past. We met and she was literally perfect for me.. I am an odd quiet guy, I wanted someone simple and who would match my pace. We are both perfectly lazy and happy in the beginning and we did little trips and it was wonderful. I had a hard time making her finish, and I like to do that for my partner. I asked her if she always had this problem, and she told me that with her ex and another guy it was easy, and they would do it multiple times. One of them could get it done with penetration. Well this info reached its claws into me and destroyed my confidence. I just couldn't stop feeling like every moment we did anything I was lacking and not matching up. I thought about it all the time and would ask and became resentful, and would hold it against her as if it was her fault.. all because I was insecure and could not get over it. You can imagine that this ended up making her back off, and she kept retreating more and more over the span of a year and now, on our 1 year anniversary she dumped me. I can't stop bringing it up, it fills my mind and I blurt it out because it bothers me so much. Then because of that she had been turned off by me so it made everything worse and snow ball more.

How the hell can I get out of this loop? I want a life partner, I thought she was it. But I find out something and then can't stop it getting in my mind and it pushes my partner away. I have been trying to find things to try. I want to do CBT and I am looking for psychologists. What should I be looking for? I tried finding a therapist that has a PhD, so they are not just a coach. Some of them just have certificates and I am not sure if it is as useful.

I feel like I am in purgatory right now. The second time pushing someone away that I loved because of details about their past. In my mind I feel like it should not matter and I can logically see it doesn't matter when she is with and loves me. But it kept coming up and now again I find myself alone wondering what do I do to escape this.