At a party
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After you arrive, you can go with the 3s rule (recommended) or alternatively, Don Diebel: "Grab some food or a drink and notice what seems to be going on socially, what the dynamic seems to be, etc. The people who seem lost will be the easiest folk to flirt with. If you want to, you can assume that everyone is socially nervous, cut them some slack if things initially seem awkward and look for ways you can make people more comfortable." But honestly, it's much more fun to storm in with guns blazing using the 3s rule:)
See also:
Fluff talk
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