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Lila, 25 y.o.
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It seems like the topic of being single comes up every time she takes a trip with her single friends. In my personal experience, it is probably them directly influencing her to not be a drag and pointing out that they can't do as much stuff with a friend already in a relationship more than her being the one directing the mindset… which is why it wears off after a short time. My specific example would be my inlaws spending 2/3 of every visit trying to extol the benefits of moving halfway across the country to online near them, then 2 weeks of my wife actively considering it before settling back into remembering that our jobs are both here, all of our friends, all of our kids' friends… the weather there is rated at “if your AC dies, so will you”, and that, literally, the only people there would be her overall anti-social parents and sibling.
I would brace yourself for things, ask her to be completely honest with you and explain who starts off the topic of her needing to be single. Is it her or her friends? Then let her know that you don't agree, but if she's going to insist on it now, or it's just going to keep coming up every time she goes off with these people, then you need to just make it a clean break up because you need the freedom to move on and aren't just going to idle around waiting.
Make it clear that, at the best, every time she suggests her single life experiment, she is telling you that you are not enough… but if she doesn't find some sort of greener grass elsewhere, she'll settle for you, and that you refuse to be some human participation ribbon.
Dump him
he’s not a good person, he emotionally abused you, and he downright doesn’t like you. when you can’t meet his “physical standards” he chooses to destroy your self esteem. you gotta get out of this.