She looks better when she dresses to fit her size or wears more form fitting outfits e. g leggings, smart skirts, non-frumpy tops, etc. I like it when she wears these and compliment her on them all the time. This was how she dressed when we first met.
She really got into wearing non-flattering frumpers. I invited her out to a friend's house and she came looking like somebody's granny and I eventually had to bring it up to her in a sensitive way after. I asked her if she would like to go shopping to update BOTH our wardrobes (my treat).
She was good with it at first, but the day before shopping day she said she did not want to go shopping for new clothes because she thought about it and feels weird that we are primarily going shopping because I don't like how she dresses.
At which point I basically decided to let her go so she can find someone who better appreciates her chosen sense of (anti-) fashion. She ofcourse cried and all that as expected but that's done with.
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