A guy I work with told me once he liked to take his dates to Castle Rock State Park. I was already married when I took up the habit so I don’t bring a lot of direct experience on combining hiking and dating, but I do know a few things from taking my wife on hikes. To wit:

  1. Stay on trails you know by heart (wow, a pun!) and don’t do anything stupid. Nothing says “loser” like having to call in a search and rescue team.
  2. Ask about allergies ahead of time and be prepared to change all your plans on a dime if an allergic reaction happens (if she has pine-related allergies, stay out of the redwoods, for instance). Put some Benadryl in your first aid kit.
  3. Single-track trails are terrible for conversation — avoid till you get to know each other (there’ll be plenty for single-tracks to tune out annoying chit-chat about her best friend’s outlaw biker boyfriend after you’ve been dating a few months).
  4. Walk at your companion’s pace (good advice for any hike but especially when you’re trying to prove you might be worth hanging out with on future hike).
  5. Five miles is a long walk for a rookie — as long as you’re demonstrating your capacity for compassion and empathy by asking about allergies, ask probing questions about fitness (think of the payoff if you have a leg fetish!).
  6. Unabridged version of “no means no”: “I don’t like to hike” means “I don’t like to hike.”

OK, so that feels like a good start. Please weigh in with your own insights — dates from hell are especially welcome. Include some locales if they spring to mind.

(Bonus link for those who like to plan ahead).