Make love and then join the mile high club

from Big Sean (Ft. Chiddy Bang & Wiz Khalifa) – High Lyrics on Rap Genius

Meaning

There are two forms of the “mile high club”:
1. The “real one,” which is when you have sex in an airplane (being a mile high in the air) and
2. The “joke one,” when you are just really really really fucking high on weed.

This line probably refers to the first one since his penthouse is so high in the air, he’s having sex a mile high in the air, but he’s also really fucking high so both work.

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