In a dipole antenna or any other pole like antenna, there is supposedly a ground on one side causing the current to flow away and towards the ground towards the feed, but if the whole antenna itself is a good enough conductor with free electrons, how does the earthing work? Is it necessary to have an antenna such that it's resistance is higher than the ground?
As usual, electron-based thinking will lead you astray. A metal or other conductor has mobile electrons which are usually referred to as "free", but there is an overall balance of their number with the number of protons in the metal, so they are not a "surplus". The nearest thing to a surplus electron source might be a N-type semiconductor.
Dipoles and monopoles-with-ground are usually considered separately. Dipoles aren't grounded. My antenna theory is rusty so I'm going to refer you to the internet.
The important number is not resistance but impedance at the particular frequency of interest. The resistance of a good antenna is as close to zero as possible.