I'm wondering if I should tell me ex/friend to break up with his ex.
Yes, I know the title is *something* but I don't know how else to word it.
For context, me (28F) and my ex (28M) were together for 5 years. We will call him Will. We have been broken up now for around 2 years, but we remained friends, for the most part.
It might be a little jumbled. I'm not very good at story telling, without making it seem like a mess.
Anyway, down to the nitty gritty of it all.
Almost as soon as we broke up, we were still living together, Will got together with his current girlfriend (31F) we will call Amy. An online friend of his for over fourteen years.
Now, Amy was a big part of our lives when we were together. Or I guess I should say *his* life. I wouldn't say I wasn't jealous, because a lot of the time his attention would be on her, rather than me. Always playing video games, chatting on the phone, dropping what he was doing when she called with a crisis.
Yes I annoyed me. On top of him telling me, after we broke up, the whole five years we were together he was **in love** with her, that whole time. So yes, I am adult enough to admit there was some animosity. But now anymore. I'm over it.
But back to the issue at hand.
I haven't seen Will in person for 1 1/2 years since our breakup. We would talk here and there via text, but that was about it. He wouldn't really tell me about his life, and I wouldn't tell him about mine. We are friends on tiktok. He would only send me one Tiktok every few weeks.
But suddenly, starting a few months ago, he started talking to me more. Telling me about the small things happening in his life, wanting to hold conversations. Even started sending me tons of Tiktoks, every little one he found funny, and things he knew I would specifically like.
Then he texted me, reminding me that he had my stuff. (I had forgotten he had some of my belongings at his apartment). So I made a time and date to go to his apartment to get my belongings.
So when I went to his apartment to get my things, he greeted me at the door. He looked washed, groomed, smelled of heavy cologne, and was wearing a nice shirt. (Mind you, when we were dating he didn't do any of that. Barely showered, didn't like cologne, didn't own any nice clothes, and never cared about what he looked like.) So it caught me off guard a bit.
For another bout of context, Will lost his mother 2 years ago. We both were super close to her, and she was a wonderful woman. But, I know, that he hasn't grieved her death properly.
As I was grabbing my things, he hands me a little trinket that he bought for me after we broke up because "I know you like cats." I happen to notice when I was there, there was ***tons*** of empty liquor bottles in his apartment. All over the floor, kitchen counters, and splayed on his couch. They were new, I could tell.
When I asked him about it, he looked upset. Saying that he was dealing with his mother death all of a sudden, and didn't know how to cope. So I tell him "well, I am your friend. I'm always here to talk when you need someone." All he said was thanks, and I finished getting my stuff. The hug he gave me when I left was...intimate for lack of a better word.
He held onto me, buried his face in my shoulder, and squeezed me hard. I started wondering if he would start to cry.
A couple days later he messaged me saying "thank you for bringing up the alcohol. I threw away everything that I had left and I'm trying to stop drinking as much as I am."
And this is what brings me to my original point.
Amy is a **raging** alcoholic. According to Will, Amy can't sleep without getting drunk, or being high. Sometimes both. Sometimes I would be dragged into their drinking, by being told "Amy is depressed, want to have a shot?" Despite her and him drinking together on call, the night before...for the whole week.
So the last person I think would reach out to Will, ask if he's okay, or notice that he's struggling would be Amy. On top of that, since now that Will is *trying* to stop drinking, and so better for himself as a person, I don't want to see her drag him back down because she won't get better. (She hasn't. He told me she still drinks and smokes).
None of his other online friends have even checked in on him, he doesn't really have any in real life. At least none that he hangs out with. *I* am the only one who noticed his pain. (Not trying to be a savior by saying so.)
I just want what's best for him, considering I have known him for 8 years, on top of us dating. I think he's a great guy, and he deserves to be happy.
I just want to know if it would be wrong for me to mention something about maybe Amy isn't the best for him, considering his circumstances. Or would that be a horrible move to make? He isn't the best at reading the signs of when something isn't good for him, without an outside perspective.
Posted Sep 6, 2026, 3:18 AM UTC