Dear Pepper: Scheduling Slackers and Overachievers

Dear Pepper is a monthly advice-column comic by Liana Finck. If you have questions for Pepper about how to act in difficult situations, please direct them to [email protected]. Questions may be edited for brevity and clarity.

Dear Pepper,

I was born in the wrong century—I’m not a last-minute planner. Friends evade my requests to select a specific time and place to see them, saying, “Let’s check in morning of!” Or “Great, let’s play it by ear!” Or, most hair-raising, they’re just silent until the day of the proposed plan.

When this happens—and it is always happening, Pepper—I mentally start a countdown. If the plans are not solidified twenty-four hours in advance, I will make up an excuse and bail.

You might think that “Let’s play it by ear!” is a friend’s polite way of backing out of something, but I find that it rarely is. More often than not, they do expect me to meet up. They just for whatever reason can’t bear to lock in specifics till nine seconds beforehand.

I find this manipulative, rude, anxiety-inducing, and extremely disruptive. The person who accepts a plan but refuses to solidify it has a scary amount of power over their planning companion. You live in the terrible limbo of uncertainty until they deem it time to decide. And, if you then try to negotiate at zero hour, the plans will probably fall through, and you’ll have to start over again in a week or a month, or else risk being seen as someone who’s too much of a prima donna to keep as a friend.

The problem, dear Pepper, is that I do like my friends. I want to see them. “If you like them that much, then why aren’t you honest with them?” you ask? Well, I’ve tried that. I’ve gotten better at telling people, as tactfully as possible, that I need to have my schedule hammered out a couple of days in advance. You’d think that this would solve the problem, but it doesn’t. It’s been a year since I’ve seen my little sister, for example. And she lives only a mile away. This is tragic. I don’t know what to do. Advice, please?

Sincerely,
Thursday at 5:15 Sharp

Dear Thursday,

What you need is to be a little more selfish and a little less aware. Your conundrum reminds me of the way I feel when I try to do my taxes. I am aware that there is math involved—a lot of math—but I can’t figure out what kind of math, let alone actually do it. There are too many variables. When I try to focus, my head explodes. That’s why I have an accountant. My taxes get done.

There is, in your case, however, no I.R.S. looking over your shoulder to make sure that you get all your plans with friends in on time or else pay a penalty. So, rather than hire a professional to do your scheduling for you, I’d suggest that you take a more laid-back approach. My sense is that, if you were lonely enough to actually want to see all your friends regularly, you’d be better able to put up with their scheduling quirks. I also think that, if a fairy appeared and told you that all your friends would stay friends with you even if you never saw any of them again, you’d choose to have a much airier schedule. There is no such fairy, unfortunately, but here I am. Telling you not to try so hard—you can’t get an A in scheduling. And, with the free time that results from your new scheduling philosophy, I have a feeling that you’ll figure out ways to see your little sister more often.

In solidarity here,
Pepper