TL;DR:
I’ve been with my girlfriend since February, but I’m struggling with her past in online explicit content, her negative mindset about everything, and her verbally abusive behavior when she drinks. I found out she was still messaging her ex when we started dating, and I’ve historically left relationships too late. Despite all the issues, I adore her and love our day-to-day moments, but I’m unsure if things are totally right. How do you know when it’s time to leave?

When do you know it’s time to leave?

I've been in a relationship with a girl, we'll call her Shannon, since February this year. Over time, a lot of things have come up that are making me question whether I should stay in the relationship or not. I really love her, but I’m feeling stuck, and I could use some advice.

I’ve known Shannon for about seven years—we met in college, and she was my first real crush. I’ve liked her ever since, even throughout university and beyond, so this relationship has always felt special to me. It makes what I’m dealing with now a lot more difficult.

One of the first big issues was her past in online explicit content creation. When we got together, a lot of her stuff was still out there and being shared. She did everything she could to remove it, but some of it couldn’t be taken down. While it really bothered me at first, I’ve managed to put that aside for now. But it still lingered for a long time.

Another problem is that she’s incredibly negative about pretty much everything. It's not just practical things, like work or day-to-day frustrations, but her general approach to life. Every little thing turns into an issue. For example, if she's trying to figure out something like an air fryer, she’ll get frustrated and angry instead of calmly trying to solve the problem. It’s always problem, problem, problem with no effort to look for solutions. She has a job but constantly claims there’s no job in the world she could ever like. She wants a four-day work week and complains about her current job, but instead of putting time into figuring out a career path or what she might enjoy doing, she just complains endlessly about it. I’ve tried to encourage her or suggest things she could do, but it’s like she’s stuck in this mindset where nothing will ever work, and it’s exhausting. On top of that, she can be quite grumpy a lot of the time. It’s not at me, but it affects how she talks to me, and bundled with the negativity, it makes things exhausting. I’m worried that if we move in together, this constant cycle of negativity and frustration will follow us into every part of our life.

The other big issue is her behavior when she drinks. Almost every time we've been out, something has happened. She becomes verbally abusive, shouting and screaming at random things, sometimes banging her head on a bus stop, even disappearing and running around town. It’s like she spirals in her own head, and I just get caught in the middle. One time, I was even accused of assault because I was trying to help her get into a taxi after a night out. It’s never because of something I’ve done—it’s always her internal struggles taking over.

One of the worst incidents was after a night out. She got really angry because a girl talked to me, and even though I ignored the girl and left the conversation, Shannon was furious. When we got home, she started throwing things around my room and shouting while my parents were asleep upstairs. She wasn’t screaming at me, but her tone was intimidating and almost violent. She eventually stormed out of my house, with no shoes on, into the rain. I was semi-drunk and ended up driving around town at 5 a.m., over the limit, trying to find her.

To add to this, I found out that when we first started dating, she was still messaging her ex. She told me she wasn’t really in contact with him, but I later saw on her phone that she was sending him messages, saying things like "I’ll always care about you." She claimed he was suicidal and needed her support, but it still felt like she was crossing a boundary, especially since she wasn't upfront with me about it.

On top of all these issues, I have personal reasons why I find it difficult to leave relationships. Historically, I’ve left things way too late until everything falls apart, and we end up hating each other. This has been influenced by my past relationship, which lasted six years and was abusive—physically, mentally, sexually, and financially. It took me a long time to get out of that, and I don’t want to repeat the pattern of staying too long again. Also, it's embarrassing for me—Shannon’s become a part of my family, she’s met everyone, and we spend a lot of time together with my family and friends. The idea of telling everyone that another relationship hasn’t worked out is tough to swallow. That adds to the difficulty of making a decision.

Despite all of this, I still adore her. Our day-to-day moments—when we’re just watching TV, lying in bed, or going out together—are great. The foundation of the relationship feels strong, but I’m unsure if everything else is totally right.

How do you know when it’s time to leave? How do you balance love with knowing what’s best for your future?