I am definitley not an expert but yes it does matter. The board also matters a lot, probably more than the wave. A good wave is a good wave and you both should be able to surf it. If the board he is using is not big enough/buoyant enough the it would take a wave with a lot more "push" for him to surf ropeless.
What board are you using? There is a pretty big weight spread between you two. Probably will not be able to effectively use the same board.
Foster
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