“My Boyfriend’s Ex Won’t Leave Him Alone”

My boyfriend and I met ten years ago, and we had an on-again, off-again friends-with-benefits relationship for about four years while were in college and living in different states. In one of those off periods, he had a girlfriend for about eight months. At the time, this was no issue. He and I weren’t talking, neither of us was emotionally invested in the other, and I was seeing someone else. Fast forward about a year later: They had broken up, I was single, and both of us were home for the summer. We started hooking up again, and he was very honest with me that he was not over her. I had no problem with that because, to me, he was just a summer fling.

That was five years ago. We’ve been together since that summer, except for a ten-month period when his job relocated him across the country. We moved in together last year, and, for the most part, we’ve been happy, until his ex came back into the picture. They hadn’t spoken in years, until she broke up with her fiancé, got drunk, and sent him a message saying she had made a huge mistake, she still loved him, and she would wait for him forever. It threw him for a loop, but he was again honest with me, he showed me the message, and we discussed how he should respond, which was basically a “thank you, but I’ve moved on. I wish you the best.”

I thought that would be the end of it, but she won’t go away. She keeps messaging him, and while he and I were in a rough patch a few months ago, she took advantage of him. He suffers from depression, which had taken a toll on our relationship, and she has been stroking his ego and manipulating him.

In the last month things have gotten so much better. My boyfriend has started going to therapy and dealing with his depression, which has done wonders for him and for our relationship. But she still won’t go away. He told me about all the conversations they had (which I hadn’t known about at the time), and he has stopped responding to her, but it drives me crazy. I hate her for taking advantage of him in a fragile state, I hate her for getting involved in my relationship, and I hate her for not just taking no for an answer. They broke up almost seven years ago, and I can’t help but wonder if I’m going to deal with her forever.

How do I address this without seeming like a crazy jealous girlfriend? I’m trying not to be, because I do trust him, but I don’t trust her to not manipulate and hurt him while he’s trying to recover. — Tired of Dealing with His Ex

You really trust your boyfriend? Truly? Because if you did, you would not have to worry about him being manipulated or having ongoing conversations with an ex from seven years ago. He was with this woman for eight months years ago, and then one night she sends a drunken text that she had made a mistake and still loves him? The two of you should be side-eying this woman, maybe even feeling a little sorry for her, and your boyfriend should have blocked her every which way she had of reaching out to him.

If she didn’t get the message after the first “Thank you, but I’ve moved on now and I wish you the best,” then that’s on her. But if your boyfriend didn’t respond to any ongoing attempts from her to reignite something with “I have a serious girlfriend I live with, this is inappropriate, I no longer want to hear from you and will be blocking your number now,” that’s on him. I don’t care if he’s depressed or whatever label you’re using to excuse his behavior. If he were 100% committed to you, he would be 100% disengaged from this woman trying to break you up, period. This is 100% on him. HE is the one in a relationship with you. SHE owes you nothing. But he does. Tell him to cut the shit me block her ass or you’re done.

I’m wondering, since your relationship started as a summer fling, during which he confessed he wasn’t over his ex-girlfriend, and then you morphed into something more serious, if you ever got confirmation from him that he HAD gotten over the ex? Or was it left open-ended? Does he — and do you — think on some level that because he basically “warned” you years ago that he wasn’t over his ex, that this behavior is excusable? Because it’s not. And he seriously should not be living with you if an ex-girlfriend can rattle him so much and make him re-consider on any level whether, or how much, he’s committed to you.

Consider this a huge red flag for you. In a long-term relationship, you are going to have far bigger challenges than some crazy ex-girlfriend swooping in and trying break you up. If the guy you’re building a future with is so easily rattled by this, you can bet the bigger issues are going to have far more devastating consequences. 

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If you have a relationship/dating question I can help answer, you can send me your letters at wendy(AT)dearwendy.com.


  1. Ah yes, the crazy ex girlfriend who won’t leave him alone. Then the truth emerges that, despite what he allowed you to believe, he had been in contact with her the whole time. I wonder what their many conversations were about? Depression is a real thing but the extent to which you allow it to excuse his behaviour is staggering and indicates a major level of denial on your part. In case you didn’t realise, you appear to be jn the way as I see no other reason why he hasn’t blocked her on every platform. You need to have a serious, cards on the table, convo with the BF. He shouldn’t be confused about his feelings and loyalty five years in. He may be one of those ‘nice guys’ who lacks the courage to say the hard thing because he doesn’t want to be disliked. But his actions are speaking loudly.

  2. Jessesgirl says:

    No, she didn’t “take advantage of him.” And this isn’t an ex “from 7 years ago” but one from a few months ago, whom he cheated with “during a rough patch.”

    It’s not “crazy” to set boundaries and you don’t have to “trust” someone who has proven himself to be untrustworthy. Honestly, I’d move out.

  3. HeartsMum says:

    Good questions from Wendy, and a fantastically sharp response. It sounds like time to turn this on/off relationship OFF permanently. I don’t know if I could live with someone I felt that “meh” about but faulting a third party for the state of their relationship took a lot of mental gymnastics.

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