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Who would like to read a fluffy question about being nice?

Dear Captain,

I love my mom (1), I love feminism (2) and I am certain, that everyone has the right to dress as they want (3) (except for Nazi clothing, but luckily, that is not my topic). This three principles clash when I look in the drawer of my mom.

My mom is recently single again after 12 years of dating and living with her former partner. She is 65 now and a wonderful, humorous, intelligent woman. She likes dating and has an outgoing personality and wants to meet new people and eventually start a relationship again, but doesn’t mind dating for a while and having fun. She has always been the intelligent one, not the beautiful one in comparison to her sister and never cared that much about clothes, make up, and stuff (literally she puts on sunscreen and a green eyeliner. Since 40 years). Her mother, my grandmother, often asked me (or her sister) to go shopping with her, so that she can have something nice to wear. We do it sometimes, but just for fun and not because our beloved ancestor says, we have to look in a certain way to be social acceptable. She often asks me about a style choice and states, that she wants to look her best.

BUT. She sometimes dresses quite horribly. It’s hard to say and admit, but honestly – bucket hats?! Sometimes I want to say something, but when the urge comes up, I mostly stop myself because: see principle 3. It is even hard for me when she explicitly asks for my advice. Do you have any scripts how to tell her that this specific thing/the dress/the hat (!!!) is not suiting her (or anyone, in the case of bucket hats) in a nice, loving, supporting way without compromising my believe, that she should dress the way she feels most comfortable?

Your advice is highly appreciated, thank you

Daughter who is torn between her believes in feminism and the fight against socks in sandals.

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