This is one part letter to self, one part letter to friends, and one part speculation.
I have both endured and helped friends endure heartbreak of varying degrees. In spite of it all, it seems like our generation doesn’t really suffer from an overabundance of heartbreak, but a profound deficit of risk-taking. While unreciprocated love has always received some attention in cultures of practically every sort, it seems to be the dominant theme these days. We are the generation of pining, sitting on one’s hands, and avoiding grand gestures for fear of rejection.
It’s not so much that the feelings aren’t there. Love is nigh unavoidable. The willingness to put it out on the line and explain to another person exactly how you feel, though—the gesture of really, truly exposing your deepest sentiments—is what freaks most people out. And it’s not like this is anything new. Only now our generation’s heroes are the ones that wallow in their self-pitying longing and have to be pushed over the edge by external circumstances or desperation, rarely will power (see, e.g., the cultural epics of 90s television, Friends and Sex and the City).
Similarly, there is a lack of grand gestures in the other direction as well. Breakups are rarely actual breakups—instead, a breakup merely signals the start of a series of ambiguous and painful hookup sessions with your ex and other people to the point of exhaustion for both parties. The door never completely shuts because, hey, neither party was really willing to ever make a grand gesture in the first place that would have really tested both parties’ mettle. And so it goes.
Faced with difficulties that inevitably arise from these norms—and they really are becoming the norm—I dispense one bit of advice: figure your shit out. This entails a whole number of commitments, duties, and general provisions. To wit:
- Don’t start a relationship (emotional, physical, or otherwise) when someone else is on your radar. Even if the someone else is geographically distant, taken, or otherwise unavailable. If you’re unsure about someone, make a grand gesture that adequately expresses how you feel, even if that’s mostly confusion. If you don’t know what constitutes a grand gesture, ask yourself if you’re completely comfortable doing X. If the answer is no, then it’s probably a grand gesture. The other person’s response will almost always give you enough certainty to pull out of the gray area. On that note…
- You will never be absolutely certain about anything. People change. Relationship dynamics change. The other person might decide that they prefer members of the opposite/same gender. Or maybe they’ll become a furry, or decide that they have some other fetish that you can’t satisfy, or that celibacy seems like a good idea. Who knows? The fact that certainty is impossible doesn’t give you carte blanche to be a jackass, though. As such…
- There will be a gamble involved. Everything is contingent. Take a deep breath and suck it up. With great risk comes great reward. You won’t become a millionaire playing the penny slots. If you make the gamble, though, make the fucking gamble. Commit yourself to it. Really try the other person on for size. Make some grand gestures. You can’t do that with some other potential partner on the horizon. Which is why the first step is so important.
This clearly isn’t a surefire way to avoid heartbreak, but it’s really the only way to be an authentic, decent person. And really, the lack of authentic, decent people is probably at the root of all this other bullshit.

January 24th, 2010
by jay
god dammit, jesse.
January 24th, 2010
by Elaine
Yeah, pretty much.
I wrote a response last night, but it was far too long for a comment. I think a lot of this is just silly. And… pointed? And that’s irritating.
February 2nd, 2010
by Jesse
Yo, Darren. I’ll totally date you.
You hot, boy!
February 20th, 2010
by JB
Pedro de la Barca said that if love is not madness it is not love. Perhaps that’s the precondition to the grand gesture. And the grand gesture, in turn, requires a willingness to expose oneself, utterly and completely, as you suggest. Not just the body. That’s easy. Expose the mind, the soul, for lack of a better word. That’s not easy. The stakes are higher, and rejection (if it happens) cuts deeper. But true intimacy requires risk, trust, vulnerability; in short, being absolutely naked with your partner. Repeatedly.