Did he take your clothes off just like this?
Did he give you loving just like this?
Did you spend the night in his bed on the very first date?

from Drake – Brand New Lyrics on Rap Genius

Meaning

He’s hoping that he can measure up to her previous ex, if not, go beyond during their first intimate encounter.

The irony is that he’s asking more questions, hoping that the answers are positive in his favor and doesn’t hurt him….Knowledge truly is pain.

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