I am a big fan of rules-of-thumb. (If I was a more sophisticated talker, I might call them heuristics). And I have several rules of thumb with regards to how I schedule things. Now I’m a bit embarrassed to reveal these, I’m sure that almost everyone who reads this post is going to be able to think of times when I’ve done the exact opposite, but still, these are the principles that I attempt to live by.

1. Don’t schedule more than a week in advance – I hate it when you’re trying to see someone, and it’s like booking a trip to the dentist: the nearest appointment they can give you is a Tuesday afternoon three weeks from now. If you know that you can never see a person when you want to (because they never have any immediate time available), then it puts a bit of a damper on a friendship, because it’s like, “What’s the point? The most I’ll ever get out of this person is a few hours a month.”
2. Keep some free evenings – In my opinion, a person’s best and closest friends are the ones who’re comfortable texting you to be all, “Hey, what’re you doing right now? Want to hang out?” And guess what? You’re never going to make any friends like that if your answer is always, “I’m busy.” That’s why I try to keep some space in my schedule (including Fridays and Saturdays, sometimes). Admittedly, this means you spend some nights alone…but that’s not really the worst thing in the world.
3. Don’t shop around for better plans – Like everyone, I’ve had the experience of committing to a dinner with a friend and then being invited to something way better, like A ZEPPELIN RAVE! YEAH, YOU HEARD ME, A RAVE ON A ZEPELLIN!!! WOOHOOO!!!! And, like everyone, I’m tempted to ditch or reschedule my friend in order to make the zeppellin rave. Sometimes I succumb to that impulse. However, I do my best not to. In general, I try to prioritize people and relationships over experiences. The Zeppellin Rave might be amazing, but no one really expects me to be there, while my friend is actually trying to be with me.
4. Try not to commit to more than one party in a night – This is usually not a big deal for me, since, honestly, who has the energy to bounce from location to location? But sometimes I will have an afternoon thing and an evening thing and a night thing. In general, though, I don’t like it. First of all, it’s rude. It’s like, okay, you’re here, but you’ve got one foot out the door. Secondly, it cuts down on spontaneity! How’re you going to meet someone new or experience something new if you have to leave after just an hour or three?
5. Avoid meeting people in bars – I understand going out for happy hour, since sometimes it’s a nice, chill environment. But I will never understand peoples’ desire to go out in a big group, at night, to a bar. It’s noisy and expensive and you never meet anyone new. You’re basically just drinking whilst looking at other people who are also drinking. What I especially don’t understand is the bar crawl. You spend an hour in one bar and then go to another bar where you do exactly the same thing! Now if you’re going out to dance or to scam on chicks and/or dudes, then I understand (and might participate), but in most cases that is not what is happening. It’s just sitting around and drinking. No. I’d rather do that in someone’s apartment. I also don’t like the sense of expectation that surrounds a bar night. You get all dressed up and you go out and you’re like, “Wow! Now something is supposed to happen!” But it never does.
6. If it’s the first time I’ve been invited to do something with a particular social circle, then I force myself to go — In most cases, I really like the idea of meeting new people, but once the event is an hour or two away, I always think to myself, “Oh my god, I really don’t want to do this.” In these cases, I usually try to overcome that inertia and make myself go out. On a practical level, you need to go at least once or you’ll stop being invited to things. Also, on an emotional level, it’s never going to be a good time to be around new people. But once I see them at least once then the barrier is broken and from then on I’ll be much less reluctant to see them.
7. Accept most invites – As a corollary to the above, I’ll go to pretty much anything that people invite me to, and I’ll meet pretty much everyone who wants to meet me. I imagine there might someday be a point in my life where this becomes impossible, but right now there doesn’t seem to be any sense in turning away anyone who wants to know me better.
8. Avoid flaking out – There is, of course, a sliding scale on this. If it’s the sort of thing where no one is specifically expecting me to come, then I’m more likely to flake out. But yeah, I do at least try to come to things that I’ve said I’ll go to. And I like to think that I never practice the last-minute flake out: the kind where you cancel just an hour or two before (or after!) you’re supposed to show up.
9. No 45-minute meals – This must be an American thing, right? I hate leaving my apartment and getting in my car and going somewhere (sometimes ten or twenty or forty miles away!) and then the meal is over in less time than the commute.  But it can be kind of difficult to avoid. For a long time I thought that eating slower was the solution, but I’ve discovered that restaurants are pretty good at ushering you out after 45 minutes, even if there’s still food on your plate. Sometimes I have to crouch down low and guard my plate, as if I’m an ex-con, in order to stop the waiter from taking it. The solution, I find, is to eat either at pubs or at places where you order at the counter, pay upfront, and take your food back to your table.
10. Avoid making Schroedinger’s plans – Similar to shopping around for better plans is when you keep everything in a state of uncertainty until the last minute, because you’re waiting to see what else will turn up. You know, when your friend is like, “Hey, want to do something on Friday?” and you’re like, “Yeah, maybe. Let me get back to you.” I feel this temptation quite a bit, because I know that come Friday, people will be texting and stuff will come up. But on further inspection, it’s kind of crazy. Here’s someone who wants to chill with you, and you’re putting them on hold in favor of nobody: a plan that doesn’t even exist yet. Additionally, there’s an element of rudeness. Why should other people have to put their planning on hold just because you can’t commit?

Hmm, I feel like there are more, but since ten is a nice round number, I guess I’ll stop here.