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After Ash and Gligarman have been wrapped up in a web and hung up on a lamp post, why doesn't Gligar free them immediately but do this only when arrive Gligirl?

Anime logic, pal.

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The only real answer here is:

Unlogical logic (also known anime logic)

Its the same reason that electric types are good against ground types, or that ash and co. somehow meet legendary Pokemon at least once a month. It makes for better stories.

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This answer is great XD

Don't forget how Ash always forgets Pokémon he's already seen and needs his PokéDex to remember.

And in Pokémon Origins, Red's Jolteon is OHKOd by Giovanni's Rhyhorn's Thnderbolt. The catch? Jolteon's ability is Volt Absorb.

The list goes on≥
Fun fact: There were no abilities in Gen 1.
All has been made clear to me…

But there was also no Mega Evolution O.o
"Aim for the horn Pikachu"!