This does not seem like the winning strategy. Based on her overall avoidant behavior, it is most likely that she would avoid this question too. My first impression is that she is deeply depressed. I would probably be really intentional about setting up a conversation. Are there places or times of day that she seems a little better than others? I’d let her know you want to have a serious conversation and plan it for that environment. Get your child a sitter. Don’t try to flirt because she apparently is not interested in that right now. I’d ask her, are you happy with our relationship right now. Encourage her to be honest. If she isn’t open about what’s bothering her, I’d tell her straight up that you’re not happy and you want her help to figure out what to do. Tell her what you want - the ability to converse with each other, to be romantic together, and to demonstrate to your son what a healthy relationship should look like. Be frank and tell her that the way she has been acting has been really hard on you, but also be kind and tell her you want to support her, hear how she is feeling, and come up with ideas together. If you have to, tell her you are concerned that she may be depressed and ask her if that is something she resonates with. I wouldn’t bring up separation at this point. Depression creates cognitive distortions and they may lead her to say things she would otherwise regret, so don’t set the conversation up for failure like that.