Drew Hoolhorst rhetorically asks, by way of his slideshare-cum-blog-post on TheBoldItalic, “Why are San Franciscans so goddam busy all the time?”
The truth is, people are happy to make plans in SF, so long as one follows an utterly arbitrary yet highly specific protocol. After seven years of dealing with the place, this is what I advise:
1) Make plans to make plans.
If you want to meet someone in two weeks or so, gingerly bring it up as a “possibility” to which they will assuredly agree. Expect nothing more than a vague commitment, but know that this can convert to an actual brunch, dinner, lunch, coffee date, or round of drinks if you plan accordingly.
2) Secure your calendar.
Plan your weekend by Wednesday. Plan the first half of the following week by Friday. Do not plan anything on the weekend, because everyone will be too busy drinking bottomless mimosas at brunch. Do not, under any circumstances, text someone (always text, never call, they won’t answer) on a given weekend asking “if they’re up to anything” because that will imply that they might be, but you definitely aren’t, and you don’t really want to let on to that. Drink by yourself at home if you have to. It will save you the pain of the unanswered calls.
3) Deploy code words.
People will happily commit to meeting in advance, but only if you use the proper code words. If you’re trying to schedule something more than five days in advance, then rather than asking for a firm commitment, inquire if they want to “pencil something in” at a given date and time. This will immediately make your counterparty relax, and secure a spot on their calendar. Reassure them with a follow-up involving yet more vague insinuations of potential flakery: “Happy to play things by ear.” These two phrases, “pencil something in,” and “play it by ear,” will land you a spot in even the most evasive person’s schedule.
4) Tactically, tactfully invite.
Leverage and extend your social capital, but not desperately. If you’re invited to a cool party, extend a +1. If you’re meeting a group for dinner or brunch, and it’s private but porous enough to permit a guest, invite someone along. Be gracious and extend yourself, but not in a way that signifies an urge to prove yourself, even if that’s exactly what you’re trying to do.
5) Exit gracefully.
For bonus points, have something to do afterwards. If you’re meeting someone on a business-y pretext — a lunch, say — then inform your dining companion that you have a “hard stop” and bring the rendez-vous to a firm, abrupt close, then hurriedly scurry out of the restaurant at a brisk, yet still coolly composed, clip. If you’re meeting someone for more purely social purposes — say, dinner — impress and tantalize them by hinting at your subsequent plans. If you’re feeling magnanimous, or simply think they’d be a good fit for the occasion, casually invite them along, simultaneously implying that you’re putting them in good graces, but don’t really care much whether they can make it or not.
6) Flake responsibly.
It’s okay to flake, and to be late, but there are rules and parameters. Coffee meetings in a business context can be pushed around, as long as they happen within roughly two hours of their agreed-upon start time. Dinners one can be late to, so long as reasonable advance notice is provided, and one isn’t delayed by more than 15 minutes. That said, don’t be more than 5 minutes late to lunch, because the person you’re meeting probably has a hard stop an hour later, and you want to get that hour in. Brunch in an intimate group should be attended punctually, but in a larger group, you can show up either early or late, so long as you make an appearance. If it’s one-on-one, the agreed-upon start time is more of a vague suggestion than a firm commitment, but if it’s going to be pushed back, make sure this is coordinated by an elaborate cascade of text messages; again, avoid calling people, because this, for some reason, is a faux pas.
7) Birthday parties.
Birthday parties are sacred institutions and must be attended if a “Yes” RSVP is given. If you say you’re going to come and don’t, the person whose birthday it is will play it off like a nice, well-mannered San Franciscan plays anything off, smiling and saying that it’s “fine,” but know that they are secretly crushed and will never forget it.
8) The most annoying phrase in the world.
Do not, under any circumstances, read into the phrase, “we should totally hang out sometime!” no matter how enthusiastically expressed, for it is always enthusiastically expressed. “We should totally hang out sometime!” is an utterly meaningless utterance and at most means that the person won’t summarily reject your request to become their Facebook friend, even if it takes them three days to approve it.
9) At the end of the day…
Once you know someone for a while, they’re your friend for life, but always in an SF sort of way. They will always be vague, they will always be elusive, and they will always be “busy,” but when you need them, they’ll be there for you, and as long as you pencil things in, and plan accordingly, you can count on a brunch companion until the end of time.