Probably best to start of slowly... Be nice to her, show attention without being fussy. Then when you get to know each other better, comment on her tan; those subdials are a lovely sunburnt shade - but do not fall for the temptation to compliment her on sharp and crisp case, that's for much later dates.
If you feel that there is a common attraction, ask her out - "accidently" go somewhere where you get to fiddle with the GMT hand or time something with the stopwatch, be playful, but keep it classy.
When you are introduced to the parents (probably a couple of weathered old 321s or 33.3s), it's a great idea to mention that you like good old values such as column wheels and straight lugs and when taking her out, be sure to bring her back before the 12 hour counter has elapsed. Finally, it is a BAD idea to mention any chrono creep or missing lume on the parents, just plain bad.
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