Asking for a Friend: Did I Gamble On a Bad Friendship?

Dear Olive,

I just ended a terrible, joyless marriage. Most of my savings went to the divorce settlement. I have a good job, so I’m not likely to need to use my savings anytime soon. Should I use the bulk of the savings I have left to go to Iceland, or should I save it for later?

-Flying Solo

Dear Solo,

For the sake of all that is free and wild and hopeful, and assuming you have health insurance and enough cash left over in the bank to replace your carburetor if the emergency strikes tomorrow, get thee to Iceland. With the benefit of assured steady work waiting upon your return and nothing tethering you to another person’s whims and longings, you have a very Eat Pray Love opportunity here to shake off the weight of both your marriage and your divorce and (re)discover how gloriously fun and powerfully uncomfortable it can be to do things on your own. What a way to emerge from the tumult into whatever is next.

On your trip, and once you come back as a whole new you (and if Liz Gilbert has taught me anything, you will), consider what kind of life you’d like to build for the next stretch. How can you weave joy into the fabric of your days? What systems or savings goals might help you make future Icelands a part of real life, rather than a “screw it” break from all you think you should be doing? What will let meaning and delight seep back into your everyday?

That’s all later, and it’s a lot of good, important work, and it’s easier to take on when you have finances on your side (like almost anything else). In the meantime, you need an infusion of spontaneity and ease and a little recklessness, like a reformed Mr. Banks once Mary Poppins is through with him. Trust that even after you go do what you want, you’ll be able to work for what you need. What makes “later” any better a time to do that than now? In short: go fly a kite! (In Iceland.)


Dear Olive,

What do you do when you realize that all the years that you invested in a friendship could be a waste and the other party considers you to be a casual coffee friend?

-Decaf in the Dumps

Dear Decaf,

Your question is short, but it’s dense with assumptions, calculations, projections, dismissals — the emotional equivalent of a brief stroll through a very dangerous minefield. There’s also, I imagine, quite a lot of pain and fear; the swift evaporation of what seemed a stable friendship sounds shocking and brutal. So, since you’ve given me the luxury of perusing your inquiry without speeding through it, and since perhaps carefully is the best way to get through a minefield, let’s see if we can see what’s buried under the surface here.

First, what does the realization you mention look like for you? Is it a fight? A note? A game of telephone? Did you just stop calling and notice that your friend didn’t call in your stead? If there was some concrete explanation involved, some specific indication that all your friend wanted was the fair-weather coffees, you should take that person at their word and plan to call somebody else the next time you need a shoulder. (Personally, I would probably decline the casual coffees, too; the joy in such meetings, for me, is the possibility of getting to know someone better and share something more meaningful than a latte. If the uncertain future has been cut off before it even has potential, I’m not interested.)

But. If the message got to you some other way besides from the figurative horse’s mouth, I’d wait before arriving at conclusions, especially if I had reason to believe that there was something worth cherishing there to begin with. In the absence of direct assessments — most easily found on kindergarten playgrounds, unfortunately — it’s possible that something got lost in translation. Your friend, like you, is a complicated creature with a deep and sometimes turbulent inner life. (I know this because we all are, even those not yet attuned to the details.) Maybe it’s a challenge for your friend to communicate their needs or their support of you. Maybe they snap when they’re hungry. Maybe they value the friendship every bit as much as you do, but they have a stash of pent-up frustration that they’re misplacing in your lap. Without clarity, anything might be lurking under the surface. It’s why I’m an advocate for healthy confrontations: they offer a peek into the many layers of emotional possibility, under the gossip and inference and assumption. Make sure your source is sound before you toss your years of friendship into the trash.

But perhaps you’re sure, and clarity isn’t the point; investment is. Let’s talk about that word. It’s a funny one to use when it comes to friendship, which at its best is built on generous reciprocity and losing track of who bought the bagels last time. What currency does this investment take? Number of nights as wingman, secrets kept quiet, advice doled out? Suffering through their loud chewing? Tagging along to stuck-in-space movies you’d rather ignore?

“Investment,” to me, sounds like something you expect repaid. A calculated risk. And while, of course, giving your heart and attention to any relationship is a gamble, it’s not a particularly calculated one. There’s no anticipated rate of return — just a blind hope that someone will grab the hand you’re extending, hope that turns eventually to trust as you learn to see each other clearly. There are no take-backs and certainly no FDIC insurance. (…And here, we reach the extent of my banking literacy.)

You say that you invested in this friendship for years. That’s a long time to share bagels and Big Life Questions, to extend your hand into the unknown. There must have been some reciprocity, in those years, or I’m guessing you wouldn’t have continued to give your time and energy to this person. What was the response like then, before you decided that those years were a waste? Did you get braver with a friend by your side? Did you try something new? Did you develop an appreciation for two-hour-long panic attacks in movie theaters?

You grew during those years, and it sounds like your friend was there with you. How, then, could that time have been a waste? Even if this person held you back somehow, made you doubt yourself, stifled your chances, even if the relationship has been a burden you now get to ditch: what a learning experience. We all are cheated or belittled or steamrolled sometimes, and even that’s no waste if we learn how to bear it and get bigger in response. And if your time with this person was a gift to both of you, nothing about the way it changes now can negate that. Friendships grow in both directions. My closest childhood friend is now a person I catch up with in spurts a few times a year, while the friends with whom I stay up late talking about all kinds of nonsense big and small were strangers to me a year ago. Maybe in another few years they’ll be people I only see for coffee, too. But those future coffees don’t do a thing to puncture the joy we get to share now, just as distance from my former bestie doesn’t mean our history means any less to me. Your changing friendship doesn’t have to change your past either, even if it shifts the future.

One last thing. You mention casual coffees as a specter of your friendship’s superficial future like they’re inevitable, like drinking coffee means skimming over the things that matter while posting latte art on Instagram — but all of that is in of your control. You don’t have to suffer through chit-chat about trivialities if it doesn’t bring you two closer, and you don’t have to stay casual even if you do end up at the local espresso joint. Casual, after all, only refers to where you draw your boundaries. That’s entirely up to you. To ask for more from your friendship is a risk, to be sure, even less comfortable than suffering through anybody’s loud chewing. There’s little guarantee that you won’t be let down. But you don’t have to hold yourself back from reaching out your hand into that murky uncertainty. It might be met with empty space, with this friend or the next one or the one after that, maybe even after years of contact. But it will make you braver and bigger, and it will be an investment in yourself, rather than in what you might get from someone else.



For a little unprofessional advice in these uncertain times, send your questions to our anonymous portal. We want it all, from the epistemological to the inane. We’ll dig deep to find some answers in the next installment of BLARB’s advice column, Asking for a Friend.

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