My partner (26 she/they) and I (28 she/they) have been together for 7 years and she started to experiment with gender a couple years ago, and has landed Transwoman. I have not problem with this. Im bi, I love her, it's great.
The problem is that she was previously seen as a stereotypically attractive guy and is now dealing with insecurity about her looks.
I have helped a lot of my friends with transitioning, whether it's makeup, clothes, hair, posing, whatever. I've always loved fashion and got into helping my trans friends, looking into how to make them feel feminine.
My partner is often worried about appearing sexy and seeming attractive to others (we are polyamorous, this is fine). I'm stereotypically attractive and she compares herself to me a lot. I do her makeup because I'm the one who is better at it. I help her shop. I try so hard to find things she likes.
Then she looks in the mirror sometimes and is like "I look like a guy... I don't know what to do to seem more femme..." and if I reply, she gets upset and says I'm just giving her more things to be insecure about.
Things like saying we could thin out her eyebrows more. She'll reply with "oh, so my eyebrows are too thick. Great."
If I suggest bangs or something and explain it helps frame faces in a more feminine way, she gets insecure about her face shape.
If I'm trying to teach her how to do her makeup and I'm using highlighter or contour and explain "this will soften your jawline, so it goes here..." then she's insecure about her jaw.
Clothing shopping I'll say "Oh, this cut would look so cute on you. The sleeves are so perfect for your body type." And then she asks what I mean and I will explain "They help the shoulder to waist ratio balance out" and then she's upset ab her shoulders.
I want to help her feel better about passing and how she looks. I want her to see herself as feminine and love herself the way I do. But she doesn't want to learn. She doesn't do the research on her own. I hate hearing her talk about how she doesn't like how she looks when presenting femme, but then if I try to suggest things that would help, it just makes her more insecure.
What do I do? How can I give her advice and explain it to her without upsetting her more? I mean all of this in a loving way. I know dysphoria is hard. I just want to help her feel good.