It depends on when in the series. Early on, Harry would have won for sure. Later in the series, Neville became more outgoing and found his courage. He may have been able to win.
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The major protagonists in the Harry Potter books are Harry Potter and his best friends Ronald Weasley and Hermione Granger. Other protagonists include fellow schoolmates such as Neville Longbottom, Ginny Weasley and later also Luna Lovegood. Also staff members such as Albus Dumbledore and Minerva McGonagall are obvious protagonists.
Harry potter
Yes. Severus Snape was bullied by James Potter and his friends who despised Snape and his friends for bullying muggle-born students. James later joined the Order while Snape became a death eater making them enemies who fought for different sides in the war. James also married Lily Evans, the girl that Snape always loved.
The closest you can get to a Catch Phrase in Harry Potter would be the classic "Bloody Hell"
No, J.K. Rowling thought it would be too neat to match them up together. However, in the movies Neville admits to liking Luna during the final battle and both actors, Matthew Lewis and Evanna Lynch, say they think Neville and Luna would have had a summer fling.