Even Sex Columnists Get the Blues

In my adventures as a sex educator the last five years, I’ve worked with thousands of adults and teenagers across the country, designed curricula focused on healthy sexuality and relationships, trained more than 100 humans in the basics of sexuality education, and sacrificed a large portion of my free time to keep up with emerging research and trends in sexual health. I’ve done my damndest to teach people how to communicate with their partners and have great sex and fulfilling relationships, and I’m led to believe that I’ve done it well.

But in spite of that knowledge, in spite of feeling like there’s relatively little out there I haven’t yet seen or heard in my work and being someone other people routinely approach with their intimate genital concerns and thorniest relationship problems, even I am not safe from this universal truth.

Breakups really fucking blow.

I first learned this the weekend of my sixteenth birthday. I was born the day after Valentine’s Day, which means I tend to get dropped by love interests between late January and mid-February. To be fair, the pressure of a putatively romantic holiday and obligatory observance of your girlfriend’s birthday one right after the other probably isn’t worth enduring if a person is feeling ambivalent about a relationship. I get that.

But the first time it happened marked the end of my first relationship — with my first love, the person who introduced me to socialist theory, the first dude I let get to second base (under the bra, no less!) — and I was caught completely off-guard. My gut and the rumor mill supported a theory that he lost interest because I wouldn’t put out, and while I do not at all regret deciding not to let my first below-the-belt sexual experience be getting clumsily fingered in a community theater laundry room, it was nonetheless a devastating entrée into the bleak landscape of Splitsville.

That was years ago, but experience gained in the intervening years haven’t made  breaking up any less shitty. My most recent check-in at Heartbreak Hotel in July was — in retrospect — the product of a long, slow-motion train wreck that screeched fitfully along the track, on-again, off-again, for a little over a year. There were good times, of course, but it’s hard to keep that in perspective now. One day I’ll get nostalgic, but for now I’m stuck ruminating over months of missteps and mistakes, bad judgment calls and naïveté that kept me holding on longer than I should have. In moments like these, when I can’t help but overanalyze every action and word that passed between my past partners and me, searching for meaning in the madness, a way to avoid future pain, expertise can be a curse.

I’ve been asking myself the usual questions. What the hell is wrong with me? Am I destined to die alone? Am I fundamentally unlovable? Is it possible for daddy issues to be terminal? Literally why do I even still bother messing around with men? After embarking on an intense six-season journey with someone else by my side, am I ready to watch the last season of Star Trek: Deep Space Nine solo? Should I just give up on dating and get a dog?

I don’t have answers yet. Mostly, I’ve just been moping and drinking and letting the housework slide. Work has been a good distraction, as was a truly magical midnight sea kayaking expedition with a close friend. While dancing at Bubba’s the other night, shouting the line You’re from the ’70s, but I’m a ’90s bitch with as much spite as possible when “I Love It” came on also brought a small measure of satisfaction.

But mourning anything — a person, a relationship, a chapter of your life—is messy and nonlinear. The process almost never moves at the pace we’d like it to and tends to drag on long past when we’d prefer it to be over. It demands attention, a certain self-reckoning, before scabbing over and leaving us be, a little scarred but maybe better off in the end.

If someone wrote into this column asking for help getting over a breakup, I’d give them all kinds of well-intentioned tips. Spend time with people who affirm your worth! Be gentle with yourself! Rediscover hobbies or activities you didn’t have time for when you were with your ex! But sometimes your own advice is the hardest to take.

So in lieu of advice this month, I offer this: Next time a breakup lays you low, know that you’re not alone in feeling shitty and lost. Trust me, I’m an expert.

Have a question for Kaylee? Email her at This email address is being protected from spambots. You need JavaScript enabled to view it. and you may get an answer in a future edition of That’s What She Said.


Last modified onWednesday, 09 August 2017 22:05