[BreakfastBurrito]

So near the end of my last relationship, I was getting really fed up with my girlfriend's appearance. She was a cute girl, but dressed just plain sloppily, and would do this awful, no effort, hard to describe thing with her hair where she'd just wrap and weave it into this ugly bun thing at the back of her neck. Terrible. I'd look at her and always think of that scene at the beginning of American Beauty where Annette Benning would say to her daughter "Jane, are you TRYING to look unattractive??!!"

I never found a good way to broach this subject, mainly for the obvious reason that it would be very insulting, she would hold it against me forever and use it as a trump card in any subsequent argument regarding the way we treat eachother. Also, I'm pretty much a slob myself, 90% of the clothes I own are b-day or x-mas gifts or free stuff. I'm clueless with fashion and wouldn't be able to give any subtle recommendations about what to wear or changes to make to the hair. I just know what I hate. Lastly, the fact that she wasn't obsessed with her appearance was something I really liked. But there's just a sharp difference between putting too much effort into looking good and putting in no effort and looking her worst. I'm sure I couldn't have adequately conveyed this though.

What is the correct play here?

For the record, the strategy I adopted was to just act a lot less attracted to her and hope she'd get the hint. This worked, as she got a ton of new clothes, layered her hair, and even puts on a marginal amount of make-up, but she opted to break up with me before doing all this.