I can't stop comparing myself to my boyfriend's exes

This is a throwaway account because I have no one to talk to and I hope my bf never sees this. Before dating my boyfriend, I was a confident woman. I never struggled to get attention—men would approach me, treat me well, and my self-esteem was high. But since getting into this relationship, my confidence has dropped. I often compare myself to his exes, especially one woman, Jessica, whose photos I would save and compare myself to.

When we started dating, my boyfriend told me he and Jessica had broken up months earlier, mutually. In the first few months, things were great—until I met his friends.

The first time was a gathering of 20 people. He sat far from me, talking to his friends, while I was left alone to “socialise.” I felt anxious, panicked, and ended up hiding in the bathroom for an hour. The next day, he said he was embarrassed by me, compared me to his exes, and told me they were more social than me. In particular, he described Jessica as bossy, decisive, and highly extroverted—someone who thrived at parties and effortlessly worked a room. I apologised, but the experience stuck with me.

Each time I met his other friends, I stayed quiet, and he’d point out how I was “different” and say he wasn’t sure about our relationship. He’d also bring up Jessica—how she made him go to events, spend money, and how he felt “ripped off” by her—but would then say he was lucky to have me because I cared for him more and reciprocated his efforts.

He prioritised a certain female friend over me, even calling her during our vacation to ask what she wanted. I later found out she introduced him to Jessica and that he commented on her posts with hearts. This caused a huge fight; he eventually cut her off but resented me for months.

Later, I discovered Jessica had broken up with him just a day before we met, leaving a message saying, “If things ever fail, don’t forget to message me.” They’d only gone on six dates, but he and his friend still talked about how great she was. Meanwhile, he had never said much about me to them before introducing me. I also saw him complimenting other women, especially that friend.

A mutual friend later mentioned that this same friend said my boyfriend had “changed” and no longer had his old “golden retriever energy.” It made me feel like he’d been more excited about Jessica than me.

Recently, during a fight, I brought all this up. He told me I should have moved on, that it was a misunderstanding, and that his comparisons back then were stupid. He also called me a “bitch” and said I was traumatising him. When I asked if he’d been attracted to me from the start, he admitted I wasn’t his type and that at first, he wasn’t interested—he saw me as someone to hook up with. He claimed that over time he fell in love with me and I became his first love, but also admitted he initially kept me around because he thought I was out of his league.

While he has changed—stopped drinking, built a strong career, and treats me better now—I can’t shake the feeling that he’s settling. Anytime I bring up the past, he gets angry and says it traumatises him, sometimes punishing me for it. I’m torn: part of me feels I deserved better and wishes I had ended things early, but another part sees how far we’ve come and still loves him. I just can’t escape the feeling that I’ll never be enough.

Posted Aug 14, 2025, 12:38 AM UTC

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