Good advice here, but since you appear to be new to IL2 I'd go with Marabekm's suggestion as it's the simplest one:
* Make sure you all have the same game version (4.13 is probably best and has most planes)
* Practice with your friend in a dogfight mission against AI so you can get the hang of flying together and communicating
* Try a "real" mission in co-op where you only get one life each
Maybe someone could suggest some good beginner dogfight and co-op missions on Mission4Today.
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