I don’t even know where to begin. I’m stuck in one of the most painful emotional spaces I’ve ever been in. I love my girlfriend — deeply. This relationship is intense, intimate, real. She’s changed my life in many ways, and I’ve never loved anyone like this. But there’s so much mental and emotional noise that I feel like I’m crumbling under it.

The main issue is this: I’m struggling with retroactive jealousy and OCD. And a lot of it is centered around one guy from her past.

Back when she was 16, she had a casual fling with a guy who was cheating on his girlfriend (who was also her classmate) — and my girlfriend was part of that. She says she was in a bad space, had just gotten out of a terrible relationship, and wanted to feel powerful or “bad.” She and this guy would make out, and he saw her completely naked — boobs and vagina — and she saw him naked too. She only told me months into our relationship that they had kissed. The rest came out later. Finding that out wrecked me.

To make it worse, this guy wasn’t a good person. He was a womanizer, spread rumors about her after it ended, and even years later, he made her physically uncomfortable. When we had just started dating, he came to her house, flirted with her, tried to hold her hand, kept walking around half-naked, and ignored her requests to stop. All this while knowing she was in a relationship with me — and he was still in a relationship with the same girl he had cheated on back then.

I was furious, naturally. She cut him off, but it hurt that she kept him around for years, flirted with him casually (even though she says it led nowhere), and seemed to downplay the whole thing. She says she forgave him long ago and moved on, but to me, it feels like a constant trigger I can’t escape.

And the worst part? I can’t talk about this with her anymore. She shuts down. Says she was young, it was a mistake, and she’s grown. Says I need to move on. I do believe she’s grown and changed. But I can’t unsee these images in my head. I spiral. I obsess. I feel angry at her and at him, and sometimes even angry at myself for not being able to “just let it go.”

To complicate things more: • We fight often. • Our honeymoon phase is long gone. • We’ve become cynical, consumed in each other. • I feel like I’ve lost freedom and even some of my own identity. • My work and creativity are suffering. • I sometimes obsess over her looks — feeling she looked better before me — and I hate that thought, but it shows up.

She knows I once went to an escort during a rough patch in my life, and I told her the full truth. I regret it and never did it again. She says that what she did with that guy is her version of that mistake. But to me, going to an escort once (without hurting anyone) doesn’t feel as heavy as knowingly getting involved in cheating with someone toxic multiple times.

Now, we’ve decided to take a month-long break. To figure out if we really want to be together. And I don’t know what to do.

If I stay, I fear I’ll keep obsessing, keep draining myself, keep putting my mental health and career on the back burner. It feels like making this relationship work is a full-time job — and I only have so much energy. If I leave, I fear I’ll be broken, full of longing and regret. I don’t know if I’ll ever feel this kind of love again.

I feel torn between love and compatibility, fear and hope, pain and nostalgia. I don’t know what the right thing to do is anymore. Has anyone been through something like this? What helped you decide? Is this OCD making it worse, or is this my intuition saying it’s time to let go?

TL;DR: I (24M) love my girlfriend (23F) deeply, but her past — especially a naked fling with a toxic guy who was cheating on his girlfriend with her when she was 16 — is causing me intense retroactive jealousy and OCD spirals. This guy later made her uncomfortable even while we were dating, and she kept him in her life for years before cutting him off. We fight often, I feel consumed and creatively blocked, and now we’re on a month-long break. I don’t know whether to hold on or let go. I’m scared of losing this love, but also scared it’s draining me too much to be worth it.