Strategies for breaking droughts

The still under-valued Megan (non-McArdle) writes:

Moving on, Sean asked me how I flirt with the guys I like. “Well, you
know how I am usually friendly and smiley and I talk about dorky
things? Just like that, only more.” “So if you saw a guy you liked…” “I
would probably give him a hug like everyone else, and then tell him
about the things I’ve been thinking about recently. Like right now I’m
super into Geoffrey Chaucer’s blog, so I would be all ‘hah, hah, hah, and then, he makes fun of John Gower, hah hah’.”    “And you still don’t score?” said Sean.  “Remarkable.”

Here is the full and articulate post.  Here are the writer’s two (false) premonitions.  Here is some background on the competition.  Here is the author.  Please restrict your thoughts to the polite, and apply game theory if at all possible.