‘Should I make more of an effort with her son?’

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I've been involved with a married/separated woman for about a year and a half. She and her not-quite-ex were both friends of mine for many years. We all do work in creative arts and have collaborated on and off. After some time, this woman confessed her love for me. She told me she had always felt that way and wanted to know if I felt the same. After a few months of drama, I admitted that I had always felt the same attraction, but tucked it aside because she was married. Long story short, we've been involved for a year and a half. We’ve met each other's families. Everyone gets along very well.

After some time, she ran into some financial trouble, and a good friend of mine offered to help us (her) out without being asked. I took him up on it. Since then, things have been much more unstable. She dumped me a few days after that and then rescinded the next day. Then we spent a wonderful holiday weekend with my family – but she was upset because she said I don't love her son as much as I love the kids in my extended family (nieces and nephews). I don't love them the same way. Also, the kids in my family can be difficult, but their behavior is not directed at me. With her child, it's different.

Am I not making enough of an effort with her or her son? Am I not being understanding enough or supportive enough of her situation? I feel pretty resentful because I've worked so hard and tried to help her begin a new life on her own, but I also wonder if I've put my efforts in the wrong place. I've tried to be clear with her about my feelings. She admits that confrontation is not something she handles well. In my late 40s, confrontation is something I've learned not to run away from. Advice, please?

– Understanding


I don't understand why she thinks your behavior with your nieces and nephews would match the way you are with her child. Her kid is not family at the moment. If anything, you should be giving this woman alone time with her son. You can't be jumping in as a step-parent because that's not a promise you're ready to make.

It's time to have an uncomfortable conversation. You say you've "tried to help her begin a new life on her own," but that's not what she wants, it seems. She has you on this path with her – in a pretty big way. I keep going back to the lines where you said she "confessed her love," and that you were "attracted" to her. Those sound like different feelings.

This relationship started after drama. There have been money issues, a quick breakup, and ... you resent her. I have to ask: are you happy? Is this more serious than you'd like it to be?

Sit down and imagine what a great relationship would look like with her. Take some notes. Then ask her to do the same.

After that, talk. How much do your visions match? Can she talk about this calmly, with empathy?

This relationship might not be the right fit, but you won't know until you're both very clear about what you want right now. If she can't have the conversation at all, that's an answer.

– Meredith

Readers? How would you talk about this? What's happening here? What about that money thing?