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I Tried Sliding In My Crush’s DMs. And I’ll Never Initiate A Romantic Connection Again.
Love & Relationships

I Tried Sliding In My Crush’s DMs. And I’ll Never Initiate A Romantic Connection Again.

I tried sliding into my crush’s DMs like Vanessa Hudgens successfully did to her soon-to-be husband, Cole Tucker, after she met him during a Zoom meditation group call. For me, it was akin to a backfired romance in a Mara Brock Akil comedy series.


At the wiser age of 30, I stopped side-eyeing online dating and acquiesced to the possibility of finding love in the digital realm. My one rule: He has to take the lead. I wouldn’t strike up a single conversation once the confetti cues burst that we’re a match. That rule trotted out the door once I swiped on a presumably tall, brawn, and accomplished venture capitalist sporting a million-dollar smile.

The clock was ticking; our match would expire in mere hours if one of us didn’t take the gambit. Screw it. I made the first intro, and the suave VC responded. Turned out we had a close mutual friend, too.

He had an upcoming business trip but said he’d reach out once he returned. I never heard from the VC guy until one year later when I mistakenly ambled into what felt like a zombie ambush at an intimate Thanksgiving gathering our mutual friend held. Then and there, I vowed never again to take the lead at the precipice of dating!

At 36, however, I surreptitiously stumbled across a mutual acquaintance who left me breathless at one of my girlfriend’s husband’s 40th surprise birthday celebration.

Mobilized by swoon-worthy anecdotes from countless women who successfully found love because they weren’t too shy to slide into their dream man’s DMs, I heeded the enticing call to a fortuitous meme: “Ladies, this is your sign to shoot your shot.”

He strolled into the decorated backyard, late, while the rest of us were enthralled by illusory magic tricks performed by a bookish magician; the real enigma was, who is this man who’s left me utterly captivated?

I tried to excavate more intel from my girlfriend, but she was incredibly tipsy from one too many of her husband’s themed cocktails to divulge. From the time I sashayed to the bar to standing across the extended dinner table for 30 – where we locked eyes and grinned at one another – until the end of the night, where I lolled in line for photo booth fun, I noticed Mystery Crush staring back at me.

“You have tree shrub on your butt,” a handsome guy with a stocky athletic build, who’d later introduce himself as B. warned me with a heavy southern drawl, as he and Mystery Crush chuckled. I blushed in embarrassment and swept the debris off my derriere.

Bright, professional lights flashed. I shook off the flub and angled every curve on my body, accentuated by my slinky black, backless dress.

“Let’s take a pic together,” B. smiled. I peered over my shoulder, watching Mystery Crush gazing back. Why couldn’t he be as vocal and proactive as B.? I agonized.

Later, as celebratory glasses clinked, B. boldly asked for my number, in hopes of snagging a copy of our photo and getting to know each other over lunch.

“I haven’t dated anyone in almost two-and-a-half years,” I hesitated, conjuring up any truthful excuse after B. casually revealed he was close friends with Mystery Crush.

Still, my racing heart couldn’t leave the party without officially meeting Mystery Crush. I had to know if his voice, intellect, and character matched his sultry vibe.

Channeling my inner badass Beyoncé, I meandered to him and introduced myself as I firmly shook his smooth cocoa hand. Aside from us exchanging names, no in-depth camaraderie followed.

That should’ve been a clue to relinquish any lingering feelings, but as a single woman who often comes across a smattering of gentlemen who rarely generate a mutual, palpable connection–coupled with a recent missed romantic opportunity in Mexico, I felt compelled to take the leap.

Hey. It was really great meeting you. You seemed afraid to talk to me, but I was really wishing you weren’t…

I hadn’t expected him to respond, however, within a couple of days, he DM’d me with his number. I replied with mine, squealing in excitement. Maybe taking the initiative favorably worked after all?

“Don’t call him. Wait for him to call you.” My sage hair stylist instructed me as she ran her fingers through my curly coils. “Of course not. I believe in attracting, not chasing.” I grinned.

Seven days passed since I first slid into Mystery Crush’s DMs. My optimism waned as calls from family, friends, and aggressively pesky scammers filled my phone log, but none from him, leaving me temporarily deflated. I resurfaced feeling empowered for confidently seeking after what I wanted–not from a place of desperation, but from a well of self-certainty and wholeness.

I’m a type A, go-getter accustomed to proactively risking it all for the unknown and receiving unrequited outcomes. It works wonders for my career; my love life… not so much.

A month prior, I’d just returned from an invigorating solo trip to Cabo, where I met two, late-30-something eligible men while I was enjoying an al fresco brunch buffet, overlooking the Sea of Cortez. One included a charming Black resident doctor who lived near me in LA. He struck up an amusing yet fruitless conversation while we picked over steamy mini waffles and dispensed fresh pressed juice. His geeky friend, however, mustered the courage to ask for my number.

As I was boarding my flight home later that day, a white middle-aged couple, who recognized me and my flowy white linen maxi dress from brunch, probed if the cute doctor connected with me after he expressed he was smitten.

“I told him he should’ve asked you, but he said he didn’t think you were interested,” the wife lamented. “That’s too bad, because I was waiting for him to ask me.”

The doctor’s misinterpretation of my interest and lack of initiation fueled my otherwise reserved proclivity to slide into Mystery Crush’s DMs.

While I wholly believe in progressive modern-day dating and applaud women such as Vanessa Hudgens, who have the gusto to make the first move, it’s never worked in my favor.

I’m still a traditional millennial woman who appreciates the chivalrous elements of courting, and I’m perfectly content in waiting for my future love to spark the dating communication.

That’s how I’ll know he’s divinely meant for me.

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Featured image by Delmaine Donson/Getty Images

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