"If I've got a mind to, I can leap from the crow's nest and land with my sword square between the shoulder blades of a man on the deck below. Want to see how on target I can be from a good deal closer up?"
This would only have worked for about a month right after the events of HL 2.
"LADIES! I'm single, I'm interested, and I ain't spent the past sixteen years under the Combine's no-fuckin'-field! Who wants to find out what y'all've been missing?"
I'm sorry; one ought to be able to come up with all kinds of pick-up lines based on the revolution, barricades, dawning light, beautiful marble, canne de combat, valiantly striving towards the future, etc etc, and in fact fandom has, but all I can ever think of is this.
"Um, so, did you... Were the one who, uhh, fell out of heaven?" he asks, soft and hesitant. He examines his parchment, his thumbs brushing the edges and his hands shaking. "Because y-you're just so, um, prett--you're very, ah, b-beauti--"
And then he drops his paper, fumbling after it as he glances up at her, warmth blooming in his cheeks. "Oh, Shiva wept, I'm so sorry!"
Rae grins and offers him a glass of sangria. "What are you talking about? That was adorable. Sincerity's a great plus. Sound too practiced, and you sound like an asshole."
Autor fiddles with his parchment rather than the sangria. "But I did practice. I wasn't trying for adorable, I was trying for... Um. Suave. Yes," he says, and he rests his head on his arms with a groan. "I'm not suited for this."
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This would only have worked for about a month right after the events of HL 2.
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or
"Hit me with a bagel and I'll let you kiss me."
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And then he drops his paper, fumbling after it as he glances up at her, warmth blooming in his cheeks. "Oh, Shiva wept, I'm so sorry!"
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She's so proud!
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"Are you a firebender? 'Cause yer so hot."
And so on, with all the elements.
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Cheesy: You think cloud nine is fun, you should try the Ninth Ray.
I'll broaden your horizons, baby. [Dejah: Oh sweet mother, I would never...]
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~fist bump~
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...This is a real line from canon.