Long-time reader, first time writer here.

I’m a 26-year-old bi woman dating a 36-year-old man for about ten months now. The relationship itself has been amazing. He’s an incredibly sweet, caring, and affectionate guy who goes out of his way to make me feel appreciated. Not to mention, he’s super fun to hang out with! And the sex is fantastic!

There’s just one problem. He’s still friends with his ex-girlfriend. They were together for five years but broke up almost ten years ago. Normally, I have nothing against being friend with exes. I’m still friends with my previous SO and he and my boyfriend have even hung out a few times and everyone got along. But this girl has never been nice to me EVER. The few times we did hang out, before I told my boyfriend I wasn’t into it anymore, she would go from making passive aggressive comments to being a full-on bitch. The last time we hung out I honestly thought it was going to end in a physical altercation, which is also not out of character for her. She has a long history of being a violent drunk. She spent a weekend in jail for assaulting her last SO, and my boyfriend told me stories of her hitting him with a vodka bottle while they were together. Recently she attacked her own mom and my boyfriend was tasked with driving her mom to the ER.

Like I said, I told my boyfriend that I don’t want to hang out with her again. I also told him that I don’t support him being friends with her, while also recognizing that he’s an adult who can make his own choices. The thing is, he does still talk to/hang out with her, he just keeps it on the DL. I know because I’ve seen her name pop up on his phone (not in a snooping way, just happening to see while he has his phone out). The other day I heard him talking on the phone to her telling her that he would help her with something the following day, but when I asked him what his plans were for the following day he didn’t mention anything about her.

The fact that he still talks to her behind my back honestly is hurtful to me, but I don’t know what to do about it. Should I confront him? Or is this just a self-confidence issue on my part and I need to let it go and let my boyfriend make his own decisions about who to be friends with?

Girl Over Bitches

You told your boyfriend you didn't want to hang out with his awful ex anymore—can't say as I blame you—and he hasn't forced you to see her since. You also told your boyfriend that he's an adult, something he presumably knew already, and that, being an adult, he was free to make his own choices.

And he proceeded to do just that, GOB: your boyfriend has chosen to keep texting, seeing, and hanging out with his ex. He's not imposing her on you—he doesn't bring her around the house—but he didn't cut this woman out of his life. And he's keeping his contacts with her on the DL, e.g. communicating with her secretly and meeting up with her behind your back, because he doesn't want to upset you.

You describe your boyfriend as sweet, caring, and affectionate, GOB, and not bitter, selfish, and manipulative. My hunch is that he might have doormat-ish tendencies and you're not the only person your boyfriend—that sweet, caring, and affectionate guy—goes out of his way to avoid upsetting. He certainly doesn't wanna upset his ex, a woman who hit him with a vodka bottle, a woman whose mother he recently had to rush to the ER after she assaulted her. If his desire to avoid upsetting people—violent ex-girlfriends included—is paired with a conflict-avoidant interpersonal style (common among the doormat-ish), GOB, that could explain why this toxic woman remains in his life ten years after they broke up.

If you don't want him to interact with this woman at all—for your own sake (she's a bitch to you) and for his (she's a toxic and violent chaos agent)—then you should say so. Stop telling him, "I don’t support you being friends with her but you can make your own choices," and start telling him, "Cut her off or I'm out." A desire to avoid conflict with his current girlfriend—the woman who hasn't clocked him with a vodka bottle—may inspire him to power through a long overdue conflict with ex.

As prices of admission go, GOB, cutting this woman out of his life should be one your boyfriend is only too happy to pay—all things/vodka bottles considered.