Ignoring messages from the universe, I uploaded a refreshed dating profile and dove into the deep end of online dating—embracing the reality of its inevitable role in the hellacious journey of finding a mate. Even though I’d succumbed to this truth, I was vigilant not to find myself ensnared in its pitfalls. I read profiles, swiped through every last photo, and reviewed the most important questions. The idea was to scaffold a pre-screening process, warding off the crazies who’d saturated my dating life these past few years, in theory, curating a pool of viable candidates that would ultimately lead to a husband. In theory…
It took a minute, but this revised approach started working to my advantage—I was swiping left and right very judiciously, keeping a strict eye on quality over quantity, and ended up making a few connections along the way. There was one in particular that quickly rose to the top of the pack. He was cute, witty, and the answers to his questions seemed to align with what I wanted from life. We started chatting, both of us making a concerted effort to keep things PG, directing the conversation to mundane subjects like aunt Mildred, or our most recent MTA horror story. But as the day progressed, and that midday horniness snuck up on us, we expertly wove sexual innuendo into the mundane—giving new life to a conversation that would soon need life-support for survival. You know, the usual tug and tickle: “That bulge in your pants looks impressive,” or, “that mustache looks super porn-y; I’m into it.” It was fun for a bit, quippy, flirty, but his references were vague, and I couldn’t pinpoint whether or not he was a top or a bottom—information that seemed imperative to obtain while I was blinded by 3pm hormones. Now, I can find myself flexible under the right circumstances, but that completely depends on energy—and there was nothing about his energy that was inspiring me to hoist my knees to my ears. Interested in getting to the point, and not wanting to lead either of us on, I decided to give the conversation the nudge it needed. As I was forming an anecdote about bunk beds, he cut me off at the pass:
“Are you masculine?”
Oh GOODNESS! He’s one of these!
The gay community is so deeply entrenched in their own homophobia, it’s exhausting…
“Welp. I’m wearing a baseball cap, but I 100 have black glitter tennis shoes on, so…”
The text bubble filled with active ‘typing’ dots. It kept popping up and disappearing until I got bored and put the phone down. At this point, there was no way we were going to date—at best I was going to attempt to fuck the internalized self-hatred out of him, but that would be the extent of my investment.
My phone buzzed.
“Well, I bet those shoes would look great pinned over your head while I’m laying into you.”
Yikes.
I stared at those words for a second before opening the app and hunting through his profile—searching for SOMETHING that would inspire me to get on my back for this gentleman. He continued to text as I unearthed his stats…
“I love your shaved head.”
5’4”—NOPE
“Do you wear leather jackets?”
28” waist—NOPE
“Do you have boots?”
Cat owner—NOPE
“I hope you have a hairy ass.”
Top—NOPE
“Wait…I am nine inches taller than you, have a mustache, a shaved head, and you want me on my back in boots and a leather jacket while you shove your dick up my hairy ass?”
“Yes.”
“I am exceptionally open minded when it comes to sex, but…this does not compute for me. I think maybe we’re not a sexual match—at least not on my end.”
He kept texting—actually, he still texts me randomly—but I had moved all the way on after ‘28” waist.’ Good sir, this just…isn’t going to work. And nothing he was going to say would have convinced me. I ignored the sexually oriented questions on the app, thinking I was focusing my attention on the right things—the things that would land me a husband. Clearly, I was mistaken. I knew now I had to pay closer attention.
I opened the app to try again. I swiped left on half a dozen guys until the next hot one popped up. I carefully analyzed his profile. Wants a relationship, might want kids, funny, has a close relationship with his family—he was checking several boxes. After a little more digging, I decided I was happy with most of what I saw, so the next logical step was to test our sexual compatibility. Apparently, we were a 96% match—things were looking up. His answers led me to believe he was a bottom, though he didn’t come out and say it. Considering he was interested in being humiliated during sex—and was willing to fully submit to a sexual partner—I figured it was safe to assume. I held my breath, hopeful the probability was low this one would turn into a smooth-faced twink who was eager to slip it in, and swiped right.
There was a flurry of commotion—we’d matched.
I took a moment to craft an opener that would, hopefully, incorporate the perfect blend of sexuality, wit, and carefree ease—the same qualities I was looking to attract in a mate. I finally landed on something I thought captured the tone I was looking for. But after confidently hitting send, I reread my message and immediately regretted my choices. Basking in the harsh reality of a message delivered, I began to bathe in the error of my ways. My winky face was woefully misplaced, there was a spelling error…the reference to his bulbous ass wasn’t funny or sexy…in fact, it might be construed a little rapey? It was an experiment gone awry. #fail
I took a moment to beat myself up, then brushed off my message kerfuffle as another drop in the ocean of missed connections and lost men. He wasn’t the first and I’m sure he wouldn’t be the last. I was preparing my solemn return to swiping my husband into my life when the universe delivered salve for my wounds—he messaged back. Hark, a lover of gloriously awkward men! I dove into that DM so fast I gave myself carpal tunnel. I was quick to assess what level of damage control was necessary—I needed to stem the bleeding.
He seemed taken with my compliment and made no indication that what I’d sent was in any way fumbly, or off-putting…interesting. In fact, my poorly constructed message seemed to open him up. I didn’t push my luck and decided to take his acceptance at face value. We started chatting about life—he was a baker from Brooklyn who liked long walks along the East River—and, eventually, we hit a stride. We decided to exchange numbers. I was cautious given my last interaction but figured the medium of text was the next logical step if I was at all interested in seeing where this could go.
He texted first—it was a selfie from the kitchen at his bakery. He looked hot. Really hot. I immediately zoomed the photo to take him all in. His gorgeous eyes, his pecs, those sexy basketball shorts…and then my eyes stopped. There was something in his shorts that didn’t belong. Directly underneath the waistband was a lumpy mass. It was not junk-shaped…there were hard edges—and, additionally, there was something odd about the way the fabric lay over his penis. I tried to let it go, but was fascinated—drawn to this phenomenon. Regardless of how much I stared at it, I couldn’t place what was happening below his belt. I tried to let it go, but it kept gnawing at me. What the hell was it? An insulin pump? A cock ring? Was he post-op? Pre-op?
I forcibly wrestled the thoughts into submission and pushed them out of my mind. It was one of the hardest things I’ve done—harder than the edges of whatever the fuck was awkwardly tenting his shorts. I busied our conversation with unrelated topics, but occasionally the thoughts would creep from the dark corner where they’d been placed—and my subconscious mind would sneakily integrate the subject into conversation. Each time he refused to take the bait. Eventually, I eased up and focused both my conscious and subconscious mind on the original goal—the reason I’d downloaded the app—to find a mate. I had to let it go, officially. We talked about family, goals, his favorite pastry…and then I couldn’t take it anymore. I was wrong—it was impossible to let it go. I had to see it in person. I asked to meet. I figured, if I could plan drinks early enough after a shift at the bakery, he might show up in his work shorts—which would give me an opportunity to see the conundrum in person.
“Sure, tomorrow works. I could get to Chelsea by 5:30—right after my shift.”
Perfect!
Scheduling the date so soon after this initial discovery was essential for my curiosity. If I had to wait any longer, I know I’d have brought it up over text—and I felt like this was better to tackle face to face. His shift ending immediately before was a convenient stroke of luck—increasing the likeliness he would show up in his work clothes, giving me an opportunity to assess the situation in-person. A situation which would only be mildly obstructed by a thin layer of fabric. That’s assuming it would still be there. Was it removable? What if he showed up and everything presented predictably? This was quickly shifting from a date to a Jessica Fletcher case begging to be solved. Our meeting couldn’t come soon enough.
I woke up the morning of our date miserably distracted—and any hope for productivity was futile. I skated through the rest of the day, eager for my mission to commence, and at precisely 5pm—I bolted out of the office and arrived earlier than I should have. I wanted to find a place at the bar, hoping the exposure of the stools would offer me a prime vantage point. Unfortunately the weather was perfect, and the city had clocked its inhabitants out early—everyone was there. I found a high-top in the middle of the restaurant. It wasn’t going to offer me the view I craved, but I was hopeful I’d get an eye-full as he walked in.
From my chosen vantage point, I was able to spot him the minute he walked through the door, immediately clocking his work sweatpants. Athleisure-adjacent—not completely inappropriate for a date, but because of the information they’d provide, I didn’t care.
I made eye contact—I’m not a complete animal—then waved him over. As he navigated the crowded bar, he was forced to look down to keep his footing. I was thankful for the crowd as it presented an essential moment for shameless crotch-gawking. He bobbed and weaved his way through the masses while I attempted to sneak a peek. It wasn’t until he arrived at the table that I was able to get the full frontal I was yearning for. And I was not disappointed. The hard, lumpy edges were there, staring at me—flirting with my curious mind.
I looked up to say hello and was greeted with a wink. Had he seen me? Had he caught me staring at his go-go-gadget cock and instead of looking put-off or upset, winked in response?
Huh… I don’t, ummmm…
“Hi, I’m The Baker.”
His response threw me.
So, he very clearly knew he had something out of the ordinary happening down there, but not something he seemed in any way ashamed of. In fact, he almost seemed to embrace—nay, revel—in the sensuality of his secret. What WAS it!?
I played it cool as he sat down and we began our date—or, as I had begun referring to it, The Case of the Chunky Monkey.
“How was work? What all did you bake today?”
He said something, but, honestly, I wasn’t listening.
“I’m sorry—I hate to interrupt you, but…what’s happening south of your belly button? I noticed it in the picture you sent and now it looks even more pronounced. I just...I hope I’m not overstepping my bounds, but I can’t seem to concentrate on anything else.”
“What do you mean?” he asked mischievously—yet simultaneously doused in innocence.
Fuck. Had I said something I shouldn’t have? I mean—there was definitely something happening down there that was not biologically consistent with what was happening with me. It was impossible not to know what I was talking about, wasn’t it?
“Well…it looks like there’s…ummm…what are those hard edges at the top of your penis?”
“Oh, that,” he winked.
And then everything started moving in slow motion.
He stood.
What’s happening?
He braced himself on the table as he shimmied out from between the heavy stool and awkwardly high table.
Why is he getting out of his seat?
My mind was going a mile a minute. What could this man be doing? I’d unknowingly opened a portal of mystery more frenzied than I first thought.
He rounded the table and again I was accosted by his weird crotch edges.
He came in close to me.
He whispered something I couldn’t quite make out, then stepped back slightly, creating strategic space and angling his body away from prying eyes.
I held my breath.
The Baker drug his thumbs along his pelvis, hooking them beneath the waistband of his pants.
What. Is. Happening?!
Everything began moving in slow motion as this grown man slid his pants down. My eyes wanted to dart around the room to ensure we weren’t being watched—but his pubes began to emerge and I couldn’t look away. I was mesmerized. He was actually pulling his sweats down in the middle of this restaurant…
Everything came whirling into focus as his pants continued their descent and his bush asserted its bloom. And then, from under a bristly tumbleweed of manhood appeared the harsh edges that had been occupying my brain. A hard, sharp piece of hot pink plastic came into view.
This man was wearing a cock-cage.
And he was showing it to me in the middle of a restaurant.
Sir…you just came from making pastries, you really needed to lock your shit up for that? I didn’t know what to do. In fact, I don’t even remember what happened on the rest of the date—I must have blacked out. I mean, this man pulled his locked up dick out in the middle of a restaurant! He’d unsheathed it like a child fascinated by the initial discovery of his genitals. Sweet Christ…
To add insult to injury? He ghosted me after that. HE ghosted ME. #blessed
To be honest, I’m not sure why I wasn’t the one to ghost him, but I think, even with this level of tomfoolery, the idea of yet another failed date was too heavy a burden to bear. For the record, I now also respond to moniker Desperate Debbie.
I thought I was ready to jump back into this whole dating thing, but I guess I was wrong. I think I need to wait a while longer before I’m released from my cage…