Dating In Your 40's: A Diary of Dejection

How I learned to stop worrying and embrace my inner weirdo

This piece from the archives was written for a story show called “Guts and Glory”, a popular Chicago series that ran from 2012 to 2015. Created and hosted by Keith Ecker and Samantha Irby (you might know her from her Substack “bitches gotta eat!” as well as innumerable other dazzling writing credits), the show was billed as “live lit for the lionhearted” and it did not disappoint.

I commissioned a local artist (Betsy Frymire) to create some illustrations for this piece. At the time I envisioned using them for a mixed media video presentation of sorts but it never got off the ground. Seemed a shame to let them linger in my Google drive another minute. They add so much beauty to the darkness.

Congratulations, Eileen, you finally did it. You broke out of that long term relationship and moved to Chicago. You should go wild. You should go see Tori Amos before you even think about buying furniture. You can sleep on the floor for a week or two. You should go have drinks, you should see some live music. You need to make up for lost time, you should go a little crazy.

You should start writing all of your crazy down. Ooh, cool, there’s a place that you can read your crazy and people will listen? That’s incredible. Yeah, definitely do that. But make sure it’s really crazy, like get on the internet night and day talking to nutcases every minute that you’re not out seeing music or getting wasted or both. Meet anyone from the internet that doesn’t seem like they’re actively itching to kill you. Date that guy in rural Wisconsin so you can eat the antelope he killed with a bow and arrow. That will make you feel oh so adventurous. Break up with him after you grow tired of pretending that you’re outdoorsy, because, really, who are you kidding? You don’t look good in plaid.

Oh, look, you’re still drinking a ton, but now you’re too tired to go out. It's good you finally bought a couch, but you shouldn't become one with it. Wow, you should really get out of that bathrobe. You’re starting to smell pretty bad. You should return some phone calls. You kinda took that “going crazy” idea a bit too seriously. You really should get off the internet and take a shower. You might want to slow down on the wine and get a grip on yourself.

Oh, thank God, you took my advice. That August you spent in a sweaty bathrobe was a disgraceful blip, like an unfortunate and excruciating vacation. Just wait until next year when you break up with that banker who was such a jerk. Holy shit, what were you thinking with that guy? He wasn’t even divorced and you bought that clown a Bose radio for Christmas! You didn't say a single thing when he repeatedly interrupted you to blurt out things that were completely unrelated to what you were talking about. You would just nod like an idiot after every story show where he gave you advice on how you could be funnier, when he illustrated all the ways that you could be better than you are. You finally told him you wouldn’t put up with it, thinking all he needed was an ultimatum to realize how great you were. Yeah, that plan totally backfired. The funk that followed that fiasco was like the worst kind of part time job. For months you were fine when you were working, when you stayed busy, but you couldn’t bear to have sleepovers with your worst enemy, YOU.  Remember when you would crash on your friends’ couches so you didn’t have to be alone? Ugh. So humiliating.

But you bounced back yet again. You dated a bunch of people, so you became really well versed in pretending to like all kinds of things you didn’t really care for, like those articles they wrote for "Cat Fancy" and endless pictures of motorcycles and rape fantasies.  But who cares, you were a size 6 and you were out there killing it. Congratulations, lady, you managed to pull it together. 

Oh, but let's not pat ourselves on the back quite yet. That period of skinny, breezy confidence went by in an instant. When the next summer came around, you got SO fucking low. You were overcome, day in, day out, by a head full of discordant noise, a screeching symphony of sad notes punctuated by the mantra, “I CAN’T”. You couldn’t get dressed, you could barely make it to work, you couldn’t write, you couldn’t go to story shows, you couldn’t do a goddamn thing. Wow. You just laid in your bed and did absolutely nothing but wallow in a rank pool of pity. Your depression upgraded itself to a full time position and you felt powerless to do anything about it.  Food wasn’t sustenance, it was pain relief. Booze wasn’t happy hour, it was a volume knob for the cacophony inside your head. Another thing you couldn’t do was sleep, because at night the voices got more specific, berating you for letting every man you’d ever been with steal from you. Steal your time, your money, your body, your jokes, your spirit. They stole whatever hope you managed to not let slip through your grasp. You were furious until you had to admit that you gave that shit away with a big sign that said FREE or TAKE IT or whatever kind of sign you put on items that you deem to have no value. 

Then you went into a super sized shame spiral, indulging in everything in your path to try to keep from slipping further into the muck. More food. More booze. More insomnia. More screeching. In a matter of months you’re struggling with the zipper on a pair of size 14 jeans. Look at you. You’re a disgrace. You thank God you have no children or pets or houseplants that depend on you, but you're haunted by the notion that those sort of commitments are precisely what keeps people together when the world gets too wobbly.

I’ve been meaning to ask you, why did you break up with that first guy? I mean, your emotional connection was akin to a double blank domino, but he was FINE. You weren’t married but you had a forever assumption kind of thing in place. Isn’t that all a person really needs? He didn’t cheat on you, he’d often advise you not to get too skinny and he wasn't judgmental when you wandered the house in an Ambien haze eating cookies. Sure, he’d stare blankly and nod when you talked about big plans that involved him and then he’d just go ahead and do whatever he was going to do anyway, but isn’t that what people do when they need some space? He accepted you for exactly who you were but somehow you were unable to pretend that was enough for you. You wanted him to be genuinely excited about being with you, what a joke.

Now you’re stuck going out on dates in your 40s, where there’s no more flowery talk of “making a life together”. There’s only will you or will you not want to fuck this Dad type character in a Costco golf shirt after an entire evening of listening to him talk about himself. Sure, why not. Clearly I’ve proven I can pretend to like worse things. 

************************* INTERMISSION FOR CIGARETTES********************************

But don’t worry, there are better days ahead. After I spent an unspeakable amount of time slogging my way out of the hole, I came out the other side, roughly reimagined. For me it wasn't Wellbutrin or St John's Wort or yoga or sobriety or Jesus or meditation or hours of talking about my mother's shortcomings. I had to spend thousands of days trying all of these things and more, unwittingly covering myself with more dirt while attempting to dig my way out before there was anything remotely resembling change. I shed my skin like a snake and some days it was more painful than having it torn off against my will until I woke up to hear the glorious sound of silence inside of my head. I got up and took a shower and I went to work. I begin to write again, recounting how my last five years were like a roller coaster ride without a safety bar. I went to story shows and heard others talk about how their rides are much like mine; exhilarating and mundane and awful. I no longer felt like I was slowly suffocating. I stopped pretending to like things I don't, this in turn helped my internal editor to go on hiatus. I began saying things out loud that I’d been thinking for years, blurting out stuff like  “I don’t think that’s true!” and “That’s a terrible idea!” Not only did no one die from shock, some people actually agreed with me. I stopped feeling the need to fake laugh at things that are not funny just to be polite. I let all of that slide through my hands like sand. I morphed into one of those people I'd always admired growing up. A black sheep, an outlier, a moody, mouthy weirdo.

I now embrace eating and sipping the occasional glass of wine as they are a complement to my life, not a crutch. I share them with friends who I adore and I feel at peace. I am able to sleep once again, content that there are so many ways I can truly enjoy myself. There's no need to tolerate shit with hopes of fitting in. I find joy in middle aged lady stuff like loose leaf tea and TED talks and comfortable shoes purchased with Kohl's coupons. I finally understand that I am not a puzzle that’s missing a dick shaped piece. I am as close as I've ever been to being whole. I feel in my bones that the years I spent submerged in the deep end of the darkness were a mourning period; a time to bury that girl who sacrificed her personality and her decision making power to the whim of public opinion for four decades. I see pictures of that girl and I say goodbye, grateful that I managed to crawl free of the wreckage, relieved that she was the one to perish and not me.