Don’t just tell her she’s pretty when she’s asking you to tell her all the time how pretty you think she is or when pretty things remind you of her like flowers are pretty music or a work of art or really anything, also bring up randomly one day that that was your first thought the first time you saw her you could phrase it like “ you know the first time I saw you the only thing I could think about was how pretty you were” or something like that put it into your own words

21

Unfortunately there's not much you can do, that type of thing is a very deep rooted insecurity that she'll need to work on herself. Just keep doing what you're doing and ask if she would like help with anything to feel prettier. Also take her on a nicer date more often, doesn't mean expensive, just something where she can put on a nice dress/clothes and feel good about herself instead of just work and coming home to change to pj/at home clothes

17

I try not to be the possessive type, but it genuinely makes me feel a bit annoyed (not at her) that they’re staring at her so much. And also because it makes her even more insecure when people stare at her, I genuinely don’t know what to do. I’ve tried words, literally body worship when we’re in bed and I think it’s been improving, but it’s like the insecurity is always there and it makes me sad whenever she feels this way

14

I would say keep doing what you’re doing. Her being “humble about her looks” is not necessarily a bad thing. I think that as you continue to praise her and she realizes how YOU see her, that will hugely boost her confidence

9