I need advice on giving advice. There's a friend of mine, let's call him Steven, and his ex, let's call her Jacky (mostly because their personalities remind me of Steven and Jacky from 70's show). So, they've been dating, and Jacky kind of... broke up with him after a month of heatless relations. At first, he took it a bit too harsh. But after about a day, he just didn't care anymore (atleast that's what he said, and how he acted). There was the usual "Let's stay friends" phrase tossed around, but it's sort of inevitable here- We all belong to the same social circles, nothing can stop them from seeing each other all the time. At some point, Jacky started seeking his attention all the time. My take on this: Her ego was hurt, because she thought he'd react badly to the whole thing. In other words, she was expecting an ego boost of a clingy reaction, didn't get it, and tried to get his approval. After a while, he decided he wanted to get her back, and consulted me about it. He described just about what he wants, and what I gathered was, that he just felt comfortable being with her, and doesn't necessarily want her, per se. I told him that, he thought about it, and concluded I'm right, but that he "can't help it". He also said that them hanging out in the same places and with the same friends doesn't make it easier for him. After a while, because of her attention-seeking behaviour, he started despising her. Oddly enough, he still wants to get back together with her. Both things that he claimed and clarified to me personally. He recently found out she's into him. For some stupid, stupid reason, he now feels that he should "get back at her" for her behaviour. He wants to play with her feelings, basically. I feel bad for the poor girl, and would like to stop that. I tried explaining to him that revenge isn't only dumb on it's own, but that it makes absolutely no sense in that specific case - she didn't do anything that comes even close to worthy of what he's planning. I tried telling him to just ignore her, or go for some other girl, or best- do both. But he wouldn't listen. I tried telling him I thought too highly of him, and that I didn't expect anything like that from him- but he foolishly said he'll "make it up to me", followed by some sort of promise... Eh. I think I could reason with him, but I'm not sure how. Some more details- Neither me nor Jacky like each other too much. Talking to her directly is pretty much not an option. That guy is usually not that stupid, and is usually a good person. I have no idea what's gotten into him. I don't want to get more people into this, for different reasons. Can't think of anything else right now.