Some failed late 18th- and early 19th-century pick-up lines from Jane Austen

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Loosely defined as any occasion on which a young man is trying to impress and/or attract a young woman, and is conspicuously failing.
(See also Sir Edward Denham's failed efforts to impress Charlotte Heywood, from Sanditon.)

Mr. Rushworth to Maria Bertram, Mansfield Park:
"Maria, with only Mr. Rushworth to attend to her, [was] doomed to the repeated details of his day's sport, good or bad, his boast of his dogs, his jealousy of his neighbours, his doubts of their [hunting] qualifications, and his zeal after poachers -- subjects which will not find their way to female feelings without some talent on one side, or some attachment on the other."
Mr. Gould to Jane Austen, as reported in her letter of June 2nd, 1799:
"We had a Miss North and a Mr. Gould of our party; the latter walked home with me after tea. He is a very young man, just entered of Oxford, wears spectacles, and has heard that Evelina was written by Dr. Johnson." [This 1778 novel was actually written by Frances Burney.]
John Thorpe to Catherine Morland, Northanger Abbey:
"John Thorpe... was a stout young man of middling height, who, with a plain face and ungraceful form, seemed fearful of being too handsome unless he wore the dress of a groom, and too much like a gentleman unless he were easy where he ought to be civil, and impudent where he might be allowed to be easy."
"Thorpe's ideas then all reverted to the merits of his own equipage, and she was called on to admire the spirit and freedom with which his horse moved along, and the ease which his paces, as well as the excellence of the springs, gave the motion of the carriage. She followed him in all his admiration as well as she could. To go before or beyond him was impossible ... she could strike out nothing new in commendation, but she readily echoed whatever he chose to assert, and it was finally settled between them without any difficulty that his equipage was altogether the most complete of its kind in England, his carriage the neatest, his horse the best goer, and himself the best coachman."
"...All the rest of his conversation, or rather talk, began and ended with himself and his own concerns. He told her of horses which he had bought for a trifle and sold for incredible sums; of racing matches, in which his judgment had infallibly foretold the winner; of shooting parties, in which he had killed more birds (though without having one good shot) than all his companions together; and described to her some famous day's sport, with the fox-hounds, in which his foresight and skill in directing the dogs had repaired the mistakes of the most experienced huntsman, and in which the boldness of his riding, though it had never endangered his own life for a moment, had been constantly leading others into difficulties, which he calmly concluded, had broken the necks of many."
"Little as Catherine was in the habit of judging for herself, and unfixed as were her general notions of what men ought to be, she could not entirely repress a doubt, while she bore with the effusions of his endless conceit, of his being altogether completely agreeable. It was a bold surmise, for he was [her friend] Isabella's brother; and she had been assured by [her brother] James that his manners would recommend him to all her sex; but in spite of this, the extreme weariness of his company, which crept over her before they had been out an hour, and which continued unceasingly to increase till they stopped in Pulteney Street again, induced her, in some small degree, to resist such high authority, and to distrust his powers of giving universal pleasure."
Mr. Collins to Elizabeth Bennet, Pride and Prejudice [after she has several times tried to convince him that she is serious in turning down his proposal of marriage]:
"You must give me leave to flatter myself that your refusal of my addresses is merely words of course. My reasons for believing it are briefly these: -- It does not appear to me that the establishment I can offer would be any other than highly desirable; and you should take it into farther consideration that in spite of your manifold attractions, it is by no means certain that another offer of marriage may ever be made you. Your portion [wealth] is unhappily so small that it will in all likelihood undo the effects of your loveliness and amiable qualifications. As I must therefore conclude that you are not serious in your rejection of me, I shall chuse to attribute it to your wish of increasing my love by suspense, according to the usual practice of elegant females."

For an example of a young man's success in impressing and attracting a young woman see Henry Tilney and Catherine Morland on marriage vs. dancing, the walk to Beechen Cliff (Henry and Eleanor Tilney with Catherine Morland), and Henry Tilney's pseudo-gothic satire, all from Northanger Abbey.

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