let rowan give you head

it means that you should let the famous individual named rowan go down on you and give some head or as some may call it , oral sex.

"to relieve your stress, you should let rowan give you head."

looking you upside your head

Looking you upside your head means to look at you in a crazy manner due to something that's going on crazy around you due to your allowance.

That wench was looking you upside your head like she had a problem with you.