Broke the glass ceiling

To overcome many obstacles to achieve a goal that was previously unattainable.

Boy 1: Did you ask that girl out on a date yet?
Boy 2: Yes, I just did.
Boy 1: Wow! You really broke the glass ceiling!

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Broke the glass

When one person is reading a repeat negative reaction as a positive one, and the negative reacting person makes it clear they don't enjoy that behavior.

Tammy really broke the glass when she told me she didn't like my dad jokes. I've been getting that same awkward smile for a year!