You may have to translate for we non-seattleites.
I think the whole thing is a spoof. Here is the third letter from that site:
Dear Uptight Seattleite,
Self-conscious about my new boyfriend’s thinning hair, I blurted out to my friends that he has cancer. Is it OK to ask him to play along?Girlfriend With a Baldy
Dear Girlfriend,
A crackling current runs through a new relationship, generated by the unspoken struggle for dominance. Who will be the one in control, and who will live in fear of being dumped? That’s sort of how I remember it, anyway, though I will confess to a bit of a prolonged dry spell. That kind of grappling doesn’t generally work out for me somehow. I do better at scaling a hill in a national park than winning a heart in a natural chest. But let’s reach back through all the preceding hill-grappling to reconnect with the electricity in the first sentence. Let’s use it to raise the curtain on my suggestion for you: Ride this playful, dangerous energy toward a thrillingly unpredictable ending. Look him in the eyes and ask: “What can I do for you in exchange for your feigning cancer tonight?”
Don’t know anything about the poster, but trying, maybe unsucessfully, to be funny doesn’t seem to be a zotable offense; but that’s just me. The column, taken as a whole, seemed pretty funny. Maybe Onion or Scrappleface material.