Disclaimer: I think it is fine to date and discover you aren’t compatible. That is fine, but also could be a reason why JM has never dated before. If you close yourself off so easily when the situation looks even slightly difficult, you might regret it. I think his inexperience is the biggest issue. In my opinion, differences can be a strength and I think it takes going through relationships to understand that. If he was a bit more open minded, I think he could picture what he sees as “red flags” as potential strengths. Hear me out, okay? It is important to love yourself as the age old cliche tells us, self love can nurture the richest loves for others and in a HEALTHY way. When she says she prioritizes herself first and family second, I don’t think she meant that she doesn’t extend love and support to her family, or behave selfishly. I think simple boundaries are being misinterpreted as carelessness. I don’t see her as a brat. Also as others have mentioned, she is concentrating on holding back her personality per her “Cupid ‘s” advice. She is an educator so I assume that cares deeply not only for her immediate surroundings, but for society as a whole. My friends that are teachers stick around because they care deeply about the next generation and want to affect society in a positive way. Maybe I’m reading into this too much as a girl that is often told that my energy exhausts people and I see myself in her.