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Harry, Gwen and Pete meet the first time
Amazing Spider-Man #31
To say they’re not exactly friends from the start would be an understatement. Pete’s usual standoffishness is only made worse because Aunt May is sick at the time.
Harry reacts about as well as you expect, calling him a square, and trying to prank him. He extends the olive branch, at Gwen’s behest, inviting Peter out for a coke; but Peter blows him off for Spider stuff as is his pattern.
As an aside, the way Ditko draws Harry’s face in this issue makes him look like a skeleton.
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