Charley* started it by sending me a simple OkCupid message from two Connecticut towns over, saying hi (just hi), looking about five times too handsome for me. He wore a mean scowl in his profile picture, which probably should have turned me off. Of course, it did the opposite.
I responded with substance, and he hit me back immediately with another one-word message. Cool. We went back and forth like this for a few rounds — me offering sentences, Charley offering words — and it wasn’t long before he got to the point and invited me to his place.
I knew how things would turn out if I accepted the offer: I’d hate myself.
I was 24 and finally starting to recognize that my self-esteem was shit, a fact repeatedly evidenced by my habit of helplessly attaching feelings to blowjobs that didn’t warrant them. I discarded nice guys with a strong post-sex coldness and scared the bad ones away with an even stronger post-sex neediness — an affliction that’s so textbook (see: Carrie Bradshaw, Kristen Wiig’s character in Bridesmaids, Marnie in Girls, Sam Smith in general, etc.) I could puke, but one from which I suffered nonetheless. Ready to take a step toward breaking the cycle, I told Charley no.
And then he continued to casually pursue me for two whole years.
I say “casually” because he was anything but enthusiastic. We’d just be absent from each other’s smartphones for three months, say, and then I’d get a random Grindr message late on a Sunday night asking me to meet up. Another three would go by and we’d match on Tinder. Come cuddle, he’d write.
I always flirted heavily and politely declined at the last minute, making a game out of contradicting myself. It was the best I could do — attention from attractive men is insecurity catnip. Ignoring it entirely wasn’t an option.
One Saturday morning last summer, Charley asked me out to dinner.
An actual date!
This tiny gesture morphed quickly into an excuse for me to maybe-sort-of believe he had finally decided I was worth knowing as a person, which morphed quickly into the resurrection of my delusional old hope that I could make a bad boy good (for a weekend?) — which morphed quickly into me saying, “Sure. Dinner would be great.”
Meeting him felt a bit unreal at first, given the buildup. He was just as scowl-y and cool over dinner as he was via smartphone, but now he was in front of me drinking a craft beer. His mysterious persona persisted even when I managed to drag personal details out of him. He answered questions with “yep.” He acted and spoke and even sat as if whatever was in front of him was his, or at least could be if he wanted it to. I desperately hoped he wanted it to.
Charley and I kissed before parting ways in the parking lot, yet I still drove home wondering if he liked me.
I could’ve made out with you for five more hours, he wrote to me before bed, filling my chest with a mix of butterflies and confusion. Goodnight stud.
We went on a few more dates after that, both fraught with the same uncertainty yet resulting in the same disproportionately affectionate goodnight texts. I always went to bed high on infatuation — not so much with him as a person, but with the fact that the guy who tried for two years to hook up with me now seemed to be interested in legitimate courtship. Could someone like that really be into me enough to change his noncommittal ways? I’d fall asleep telling myself yes, but would always wake up the next morning dismayed by the inevitable follow-up question: Why me?
Charley and I rarely talked about me on our dates.
Whatever it was that made me feel like Charley was too good for me ran so deep that it soon gave way to a constant state of personal anxiety. For an entire month, I scrutinized his succinct texts and stressed over when he’d ask me out next. I wondered if I should ask him out myself or if doing so would make me look desperate. I wondered if not doing so would make me look timid.
Mostly I just wondered how this man — this man I didn’t even really know, let alone genuinely like — had managed to make me revert into such a silly, pathetic version of myself.
Sometime after our fourth date, Charley didn’t respond to a text of mine for two straight days. I freaked out and mourned his disappearance as a full-on breakup. I spiraled into a self-loathing depression.
But I wasn’t entirely un-self-aware. I knew I was being ridiculous, so I used the heartbreak as an opportunity to finally seek professional help. I e-mailed four therapists, called three, and booked with one, ultimately canceling the appointment when he finally texted me back with Hi.
“There’s too much push and pull with this guy,” a friend of mine told me as Charley continued to withdraw over the next few days. “You really need to date other people, at least to take the edge off.”
So that’s what I was doing one night when I found myself out with a new guy named Graig, and we clicked.
Graig possessed a few of Charley’s qualities—the handsomeness, the confidence, the tortured-man-mystery, even — but with enough openness to allow our physical attraction to give way to a more authentic chemistry beyond it. Throughout our time together, I found myself connecting with him and having actual fun — forgetting about Charley, forgetting about my issues, and finally feeling something with someone that was easy and natural without all the triggering ambiguity.
And then I checked my phone in the bathroom.
Charley: I’m in the city. Charley: Are you out? Charley: I wanna ride home with you.
It was like he knew! I was finally not thinking about him for once. I had given up. I told him not to wait around.
Charley: I’m gonna be out late too. Charley: What train are you taking? Charley: I’m at the station. Hello? Charley: I’ll wait for you.
I was reminded of my childhood dog, a Golden Retriever with a habit of barking at a sliding porch door in my mom’s living room. Once she’d open it for him, he’d merely step outside and look around for about two seconds before turning around and carrying on with his life inside. And then she’d shut the door, and then he’d bark again, and so it would go. I suppose he just liked having options.
I reiterated to Charley that he shouldn’t wait up, but he wasn’t interested in being told no.
“There you are!” he said as I arrived at Grand Central Station over an hour later. “I’m glad I waited.”
He spent the entire ride home groping my leg; I spent it wishing he was Graig. Engaging with Charley so abruptly after having just felt a real connection with someone else illuminated how little he and I actually knew each other. Graig and I had covered more genuine ground in one night than Charley and I had in over two years.
It was with that stark juxtaposition that I finally began to accept the reality of the situation. It was never about Charley; he was merely a challenge, a blank canvas onto which I projected the generic image of the Unattainable Man — someone whose approval I was lazily confusing with my own innate lovability.
Someone whose approval, also, incidentally, didn’t mean shit.
As it all turned out, Graig and I fell in love. I’m sure this would have happened regardless of whether or not I had my train-ride epiphany, but the timing of it all was rather poetic.
To be honest, I’m disappointed, Charley wrote to me after he reached out some time later and I told him I had a boyfriend. I would’ve loved to get to the boyfriend stage with you.
I sighed, thinking about my old dog, and told him the timing must have just been off. I guess so, he replied with a sad face, and then suggested we hang out anyway.
I didn’t bother flirting. I just politely declined.
I still hear from Charley now, every three months or so, when he’ll send me a casual text message asking to meet up, checking to see if I’ve changed my mind about him, about Graig, about opening the porch door. It’s almost enough to make me wonder if I was the unattainable man all along.
*Name has been changed.
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