u/Affectionate_Age6449

My boyfriend’s past (prostitutes, threesome, casual sex) is ruining our relationship

I’m 21 (F) and my boyfriend is 31. We’ve been together for almost 2 years, and I’ve been struggling badly with retroactive jealousy to the point where I think about it every single day and I genuinely cannot get over it.

He is my third boyfriend and third person I’ve ever slept with. Meanwhile he had 2 serious relationships and his body count is 8 including me.

On the surface he can seem like a good person - caring, affectionate, loving, emotionally warm. We are also like best friends, and that makes everything even harder. I feel very close to him, very attached, and that emotional bond makes it so difficult to leave.

But his past really disturbs me and I feel like it completely changed the way I see him.

Before me, he had experiences with prostitutes (he says only twice, and that he never went again because he didn’t like it, if he is telling me the truth). What makes it even worse for me is that they were women of other races, and it makes me feel disgusting because it feels like he specifically wanted to “try” what it’s like to sleep with a woman of another race. That thought really disturbs me. He also had friends with benefits situations and even had a threesome with two girls.

He told me that although the threesome was a good experience, he would not do it again. He said he liked experiencing it at least once in his life. That hurts me because it feels like he does not actually regret it. Now, when I bring it up and get upset, he says he regrets it - but sometimes I feel like he is only saying what I want to hear.

I am not jealous of the women he was actually in relationships with. What hurts me are the one night stands, prostitutes, casual sex and how he talked about it with his friends. I found old messages where he bragged about prostitutes, objectified women, and spoke very disrespectfully about girls he slept with. It honestly made me feel sick.

Another thing that hurt me badly: there was one female friend from his main friend group, and we all hung out together multiple times. I sat there like an idiot, being friendly and completely clueless, not knowing they had slept together before. He introduced me to her and never told me. Apparently everyone else probably knew except me.

It makes me feel disgusting hanging out with him and his friends now, because they all probably know about his past, the prostitutes, the way he talked about women, and I feel like they probably look at me like I’m some naive stupid girl who accepts all of it. Like I’m the fool. I hate them now because after reading those messages I feel disappointed in men in general - not only because of him, but because his friends seem the same. It makes me want to completely shut down, isolate myself, and never have relationships again.

I compare myself to his past women all the time. I compare myself to the prostitutes, to ex situationships and ex girlfriends. I know I am attractive, I get a lot of attention from other men, but none of that seems to matter. I still compare myself to them and feel like I need to be better than them, prettier than them, more desirable than them. I keep asking him for details how they did it, in which positions etc. Sometimes I feel worse than prostitutes because he paid money for them, chose them based on appearance, wanted them so badly-and with me, sometimes I feel rejected.

This is another issue: I’m actually the one with the higher sex drive. I want sex with him more than he wants it with me. I’m very attracted to him, very physically attached, sometimes almost addicted to him. And it hurts my ego because I think: how could he want prostitutes enough to pay for them, but with me sometimes he doesn’t even want sex when I do? It makes me feel unwanted and it destroys my self-esteem.

The confusing part is that closer to our relationship, and during our relationship, I don’t find messages like that anymore. He seems different now - more emotionally attached. It feels like two completely different people and I don’t know which one is real.

At the same time, our relationship has many other issues too: debt, irresponsibility, emotional immaturity, disappearing for hours after drinking, bad influences from friends, chaos. Sometimes I feel like I love him deeply and I’m extremely attached. Other times I feel disgust and think I should leave.

I keep asking myself:

Did he actually change as a person?

Am I being unfair for judging his past?

Is this retroactive jealousy, or is this my intuition telling me I should leave?

I feel like I love him, but at the same time I’m losing respect for myself.

Should I leave or try to get over it?

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u/Affectionate_Age6449 — 2 days ago