She's not dating him against her will. He did not purchase her out of a catalog. He did not order his EA to obtain her. He did not hire Cyrano to ghostwrite poetry to woo her. She is not a 22yo intern being molested with a cigar over the Resolute Desk. Her friends did not strap her down to a table and get out a branding iron.
Why is everyone so twisted up about this? I don't get it. Is it that only guys who look like Eric Draven are supposed to date girls who look like Ms. Boucher?
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He told a obscure joke that only a very narrow sub-population of very well read students of 21st century philosophy of science would get, and she got it. That's a better "first flirt" than most.