Should i get a bob hairstyle? [Photo included]?

My hair is pretty damaged due to constant dying and straightening. But it’s still ooo-kay. I want a new look, i want to try a bob, maybe concave at the back and the front is a wee bit a-lined.

But problem is, my natural hair is kinda thick and curly (i straightened it for long hair), i am afraid it’d curl in a mess if i cut them short. Moreover, my cheeks are chubby, i scared i’d look like a dumbo if i get bob ..i’m in a dilemma. Any ideas?

P/S: If i dye my hair, i want it to be like light brown, but i am asian, i have to fix the roots often, its so troublesome. 🙁

This is me.

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