Does anyone else feel a sort of anxiety in those situations? I've been on such trips and I would rather not sleep at all than ask a stranger for help. When I'm in a position to help, I am delighted to do so, but also scared of offering.

How does one get over that fear?

Like all skills; practice. Push through the fear enough times that you learn to love it.

When I was in the military, we once had an exercise which consisted of our troop leaders dropping 60 of us in Edinburgh (Scotland) with nothing on our person except for a cheap film camera. We had to complete a list of challenges with different scores, that varied from "eat a free meal" to "play a hole at St Andrews golf course". We were picked up the following day (meaning we had to find a place to sleep the night) and had to debrief the group on what challenges we managed to complete with video evidence. To be honest, it completely changed my world view in a weekend.

We had guys who talked their way into an airfield, miles away from where we started, and convinced a random pilot to give them a spin in his private aircraft. One group managed to get the castle guards to let them fire the daily One O'Clock Gun from the top of Edinburgh castle. Another did manage to play the first hole of St Andrews (£340 a round, and a 2 hour drive away!). We had people crash a wedding, sew up a kilt, learn to play the bagpipes; it was carnage in the best kind of way.

All of that was done just by asking. At the start of the day, everyone was awkward and embarrased. By the end of day two, we all just wanted to see how much further we could take it. Turns out that sometimes all your inhibitions do is get in the way of a fun time and a great story.