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>make sure he's appropriately equipped
both in regards to enough stuff and not too much stuff. and be prepared to be assertive about this.
>be prepared to only make it half as far as you normally do
>bring better food than usual
this goes hand-in-hand with a slower pace: you can carry more, and a heavier pack will help keep you from getting antsy about moving slower. even throw a 6 pack in.
>make a fire, hang out, and bullshit
if you're really worried about it being awkward bring a third friend to help fill in conversation.
