If you want to spend time with someone who is cool, so cool in fact that they are in high demand and hard to corner for "alone time," then here is my advice: go hiking.
This guarantees that you will have several hours of uninterrupted conversation. The only other people you will encounter will be other hikers who are either a) fast athlete-types who pass by quickly; b) slow leisure-hikers (usually accompanied by children or pets) who are easy to avoid; or c) going the opposite direction. Other than that, it's just you, your cool hiking buddy, and the mountainside.
In case you're curious, I know all this good advice from recent personal experience. My sister agreed to hike with me last weekend, and we spent FIVE HOURS together! I didn't have to compete for attention with husbands (hers or mine), pets, work, or errands.
In case you get tongue-tied around your cool hiking buddy, here are some suggested conversation topics (also the product of recent personal experience since we talked all five hours without getting bored):
- Cooking. We compared notes on recent kitchen-experiments. She made a delicious sounding soup. I made quinoa salad. Good ideas were exchanged.
- Family vacation disasters. "Remember that time we forgot the tent poles? What about the trip when we got rained out and drove across-state til we found sunshine? Or how about the time I lost Elliot?" (this might be trickier if you're not talking to a sibling).
- Anonymous co-workers. This is a good source for hilarious stories because you get to freely describe your fellow employees' quirks and office drama(s). At least until your hiking buddy's boss appears on the very same trail for an impromptu introduction. Awkward.