Singles 2012: Most Eligible Chicagoans
Man seeking woman

Daniel Henderson

  • Pilot for American Airlines
  • Age: 47
  • From: San Francisco
  • Lives in: Roscoe Village

This U.S. Navy–trained pilot has lived all over the world—Australia, Japan, Central America, and Iraq—and comes with a major perk: Win his heart and you become his “registered companion,” which translates to free flights. These days Henderson pilots only domestic routes, and in his off time he enjoys working in his garden, riding his Harley, and cruising on his sailboat.

In the market for: A self-assured woman near his age who appreciates his sarcastic sense of humor and is punctual. “Reliability is really important,” he says. Divorcées are OK if their relationship baggage is carry-on size.

Conversation starter: His solo backpack journey through northern Laos.



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