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11 minutes ago, Psittac said:

a generic ibuypower headset that is uncomfortable

That's probably less that their head is large and more that the headset is poorly designed. 

 

I wouldn't necessarily say my head is massive, but it's big enough that most hats don't fit. There are very few pairs of headphones I've used that I'd deemed to be uncomfortable just because they didn't fit, the ones I have were because they put a weird amount of pressure either directly on my ears (every pair of Beats I've ever borrowed) or just in front of my ears (the HD 58X I've been using did that originally, though they seem to have worn in and I no longer notice that, or I just got used to it). 

 

Odds are if you find a pair that's just well regarded as feeling somewhat comfortable, it'll be fine with someone with a larger noggin. Granted, this will depend on just how big your friend's head is, so I'd try to figure that out first. 

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