When someone "one ups" you?

I can sorta understand when another girl one ups me. It's annoying af but it happens I suppose. But what's going on when a guy you like one ups you? A bit off putting esp. if he may or may not still like me back too. Same sex one upping is common but when the opposite sex does it. What does that mean? Why are they even doing that? All opinions welcome, thanks!
When someone "one ups" you?
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