Although a city dweller Winkle considers himself an outdoor sportsman, though he turns out to be dangerously inept when handling horses and guns.

"[2] However, Winkle is frightened at the thought of having to fight a duel with Dr Slammer, an experienced Army officer; manages to fall off a horse; accidentally shoots fellow Club member Tracy Tupman in the arm while hunting fowl;[3] cannot play cricket and who cannot even ice skate.

When leaving the witness box and realising that he had made a blunder, Winkle "rushed with delirious haste to the George and Vulture, where he was discovered some hours after, by the waiter, groaning in a hollow and dismal manner, with his head buried beneath the sofa cushions."

Winkle is transformed when he finds happiness in his love for Arabella Allen and receives Pickwick's assistance in his courting of and eventual marriage to her,[4] eloping with her despite strong opposition from Benjamin Allen, his bride's brother; from Bob Sawyer, his rival for her affections, and his own father.

[1] After his marriage Winkle finally finds the resolve to stand up to his stern father, stating: "I am sorry to have done anything which has lessened your affection for me ... but I have no reason to be ashamed of having this lady as my wife, nor you of having her for a daughter."