u/mostlyitalia

My boyfriend (35M) recently broke up with me (28F) after a year and a half together. For privacy, I’ll call him Jimmy.
We met working together at a restaurant. I started there in October, and the following February he asked me to make things official. I said yes even though I felt like I was still getting to know him. Looking back now, there were things early on that made me uncomfortable, and part of what I’m struggling with after the breakup is wondering why I kept trying so hard to make the relationship work instead of taking those feelings seriously.
Before we officially got together, we went to a rave on New Year’s Eve with his friend group. The day before, I found out his ex was going to be there. I was nervous, but I figured I could handle it as long as Jimmy made me feel secure. At one point during the night, I felt like she was trying to assert herself with me, and the whole energy became uncomfortable.
After we started dating, there were also times Jimmy would be showing me something on his phone and I would see his ex’s name pop up on Snapchat or Instagram. I realized they were still in contact. He reassured me that nothing was going on and that they were only friends. She’s part of his larger friend group, so I understood that asking him to completely cut her out wasn’t necessarily realistic, but their continued communication still bothered me.
Jimmy also has a lot of female friends. That was an adjustment for me because I’d never dated someone with so many close friendships with women. Most of the time we all hung out as a group, and there were women in the group whom I trusted completely. So my problem wasn’t simply that he had female friends.
There was one particular friend, though, who always gave me a strange feeling. I’ll call her Sam. They met in college and had supposedly been friends ever since. She lives out of the country, and I had never met her.
One day while I was working, Jimmy suddenly texted me that he, Sam, and another female friend were going to a fancy restaurant. I hadn’t even known Sam was back in town. It caught me off guard because there had been no mention of her visiting or these plans beforehand.
Another time, Jimmy had recently started his career and was doing really well. Completely out of nowhere, he said something along the lines of wishing Sam could see how well he was doing. We hadn’t been talking about her. Something about that stuck with me.
Eventually, I directly asked him whether he and Sam had ever had “a thing.” He told me no. I accepted his answer because I wanted to trust him and figured maybe my insecurity was making me read too much into their friendship.
Months later, Jimmy went away for about a week because one of his close friends was dying. During that time I noticed Sam interacting with his posts on Facebook. Months earlier I had sent her a friend request that had gone unanswered. That alone obviously doesn’t prove anything—she doesn’t owe me a Facebook friendship—but combined with the feeling I’d already had about their relationship, it brought the issue back into my head.
I called Jimmy while he was at the hospital and asked him again whether he and Sam had ever had a thing.
This time he said yes.
I know the timing of that conversation was terrible. His friend was dying, emotions were extremely high, and looking back I wish I had waited until he came home. I take responsibility for that.
But at the same time, I was devastated because I had already directly asked him this question months earlier and he’d told me no. I had spent all that time convincing myself that I was being insecure and needed to trust what he was telling me, only to find out that my intuition about there being some kind of history between them wasn’t completely unfounded.
When he came home about a week later, he broke up with me.
And that’s where I’m struggling to make sense of everything.
These weren’t the only problems throughout our relationship. Jimmy would openly check out other women in front of me. I told him repeatedly that it hurt me, but he viewed noticing attractive women as normal human behavior and didn’t see it the same way I did. From my perspective, even after knowing how much it bothered me, the behavior continued.
There were also times when his naturally charming personality came across as flirtatious to me. And throughout the relationship I often felt like I was asking for more time, effort, reassurance and consideration.
So over time I became increasingly insecure and increasingly vocal about everything that bothered me. It probably felt to him like I was constantly complaining. From my perspective, I kept bringing up the same issues because I never felt like they were actually resolved.
I can recognize that my insecurity became unhealthy for me. I don’t want to pretend I handled every situation perfectly, because I didn’t. I questioned things, overthought things and sometimes brought things up at the wrong time. I’m sure being on the receiving end of that wasn’t easy either.
But what I’m having such a difficult time accepting is that I kept trying to communicate about behaviors that were making me unhappy while simultaneously staying in the relationship and hoping things would eventually change.
He didn’t believe maintaining friendships with women he’d previously had history with was disrespectful. I did.
He didn’t view checking out other women as a significant relationship issue. I did.
I needed more transparency and reassurance surrounding certain friendships. He apparently felt like I should trust him without needing those things.
Neither of us was changing our position, yet instead of recognizing that maybe we were fundamentally incompatible and walking away myself, I stayed. I kept fighting for the relationship until eventually he was the one who left me.
And now I’m devastated over losing someone whose behavior I spent so much of the relationship being unhappy about.
That’s the part I can’t wrap my head around.
Why did I stay and keep asking someone to change things that were clearly important to him instead of accepting that his boundaries and mine were incompatible? And how do I stop blaming myself for “complaining him out of the relationship” when the things I was complaining about were also the things making me miserable?
I would genuinely appreciate outside perspectives, including if you think there are things I need to take accountability for. I’m trying to understand what happened so I don’t repeat the same dynamic in another relationship.