Yeah, honestly, who cares what someone might think or what stereotype they will throw your way. If someone is willing to write you off as a lesbian based on your hair, do you really wanna know them anyways?
Having said that, it really does depend on the person. I couldn't ever pull it off. The shortest I can go without looking stupid is just around chin length and even that's pretty weak. But that's me. My hair is really long right now, but I gotta cut it off soon. It's just too much maintenance.
Anyways, the point of my ramble here is you gotta find the length that works for you.
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-Elle-
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