My Wingman Stole Seven Women

I brought the ceramic mug to my lips and took a slow sip.

The iced coffee slid down my throat, a sharp, freezing contrast to the stifling heat of the afternoon.

Then, the male voice drifting over from the window booth made my blood run cold. It was a voice I knew better than my own.

It was Thomas.

"Babe, when are you finally going to tell him?" he asked, his tone dripping with an easy, confident affection.

The woman sitting across from him let out a soft, dismissive laugh. "Whats the rush? You know how ridiculously picky he is."

"Its been three months," the woman added, her voice taking on a whining edge. "He hasnt sent a single text to even check in."

Three months ago, my aunt had set me up on a blind date.

We met up twice. The chemistry was flat, the conversation forced, and we simply let it fade out without another word.

At the time, Thomas had thrown an arm around my shoulder and said, "Let it go, Dan. I can tell from a mile away shes a flake. Im just looking out for you, man."

My neck stiffened. Slowly, involuntarily, I turned my head toward the window.

There was Thomas. He was leaning in, resting his chin affectionately against the shoulder of the woman who had just spoken. The smile on his face was sugary, intimate, and entirely genuine.

1.

Thomas and I had been friends for ten years.

We shared a cramped dorm room in college, surviving on cheap beer and instant ramen. After graduation, we stayed in the same city. We bought each other absurd birthday gifts, hyped each other up on Instagram, and spent every holiday together when we couldn't make it home. Everyone in our social circle considered us brothers.

I thought so, too.

When I turned twenty-three, my mom started dropping heavy hints about me settling down.

"Look at Thomas," she would say over the phone. "Hes such a good friend, always keeping an eye out for a nice girl for you."

And he was.

Thomas really did keep an eye out for me.

My first setup was at twenty-three. She was the cousin of one of Thomass coworkers, a junior analyst at a corporate bank. We had one date. It was decent. Thomas told me hed ask around about her at the office. Three days later, he shook his head. "Shes toxic, man. My coworker says she has awful anger management issues. Dont even bother."

So, I didn't bother.

The second setup happened when I was twenty-four. A friend of a friend, an architectural designer. We went out twice, and she seemed genuinely interested. Thomas stepped in. "Let me vet her for you." Afterward, he pulled me aside. "Dan, shes way too slick. Shes playing games. Im telling you this because I care about youcut your losses."

I cut my losses.

The third was at twenty-five. A match from Hinge who worked in tech. We texted for a month before finally agreeing to meet. Thomas insisted on coming along to "break the ice." He showed up forty minutes late to the bar. The girl and I had been sitting in agonizing, stilted silence the entire time. She never texted me again. Thomas patted my back. "See? No patience at all. Im doing you a favor, letting you see her true colors early."

I believed him.

The fourth time. The fifth time. The sixth time.

Thomas was there for every single one.

He analyzed them, vetted them, asked the invasive questions I wouldn't"Does she have student debt?" "Is she looking for a meal ticket?"and always delivered the final verdict: Shes not the one.

I was twenty-eight now.

Seven setups. Seven failures.

And every time, Thomas was there to pour me a drink and offer his wisdom. "Dont stress it, man. Its good that you have high standards. Better to be alone than settle for the wrong person."

I would look at him. His eyes were always so unbelievably sincere.

And I would smile back.

"Yeah. No rush."

Back in the coffee shop, I sat in silence until the ice melted and my coffee was watered down to nothing.

From start to finish, Thomas never noticed me.

When he finally left, his fingers were laced tightly with the womans. As they walked past my section of the caf, he didn't even glance in my direction.

I pulled out my phone and scrolled back through my texts from three months ago.

Thomas: Shes a total flake, man. Im just looking out for you.

I stared at that glowing blue bubble for a very long time.

Then, I kept scrolling. Back in time.

The seventh setup. He said: Shes way too plain. You can do so much better.

The sixth setup. He said: Sales reps never have any work-life balance.

The fifth setup. He said: Look at her Instagram. Its all partying and expensive dinners. Shes not looking for anything serious.

Fourth. Third. Second. First.

Every single time, he had a bulletproof reason.

Every single time, I swallowed it whole.

I set my phone face down on the table and looked out the window.

The sun was beginning to set, casting long, bruised shadows across the pavement.

A memory suddenly surfaced, sharp and uninvited. After every failed date, Thomas would insist on taking me out to dinner. And over burgers or tacos, he would always ask, casually, "So, she never reached out again?"

I would say no.

And he would laugh, a bright, easy sound. "Told you. Completely unreliable."

I had never once questioned it.

But sitting there now, a cold dread pooling in my stomach

Why did he always need to confirm that they hadn't texted me?

I flipped my phone over. I didn't open our text thread. I opened Instagram.

Not my profile. Theirs.

I still followed a few of the women Id gone out with. Some hadn't blocked me or removed me.

Number seventhe one from three months agohad a private profile. Dead end.

Number sixfrom last year. I scrolled back. Two months after our date, she posted a photo at a vineyard. In the corner of the frame, there was the back of a mans shoulders.

He was wearing a distinct, vintage-wash denim shirt.

Thomas owned that exact same shirt.

My thumb hovered over the screen. I kept scrolling.

Number fivefrom two years ago. She had posted a flat-lay photo of two lattes and a slice of cake at a rustic indie caf.

I recognized the caf.

Thomas had dragged me there once. He told me it was his "secret hidden gem."

I put the phone down.

My heart was hammering against my ribs, a frantic, trapped rhythm.

But I didn't move.

Suspicion wasn't enough. I needed proof.

2.

My apartment became a war room.

Seven dates. Seven women.

I booted up my laptop and started building a master timeline. Text logs, social media screenshots, dates, timestamps, and Thomass corresponding alibis.

Date Number One. The banker. March 2019. After one meeting, Thomas labeled her "toxic." I cut contact. Three days later, Thomas posted an Instagram story tagged at a high-end sushi lounge.

I hate sushi.

Thomas had always complained about raw fish, too.

But that specific restaurant? It was the exact place Date Number One had raved about during our dinner. She said their salmon sashimi was to die for. I had even sent Thomas a screenshot of her recommendation at the time.

Date Number Two. The architect. May 2020. Thomas called her "slick." I stopped texting her. The very next week, Thomas bailed on our weekend plans, claiming he was buried in paperwork. Yet, that weekend, he posted three separate timesfrom a trendy mall, a boutique movie theater, and a Michelin-starred bistro.

Did he go to a romantic bistro by himself?

Date Number Three. Tech industry. August 2021. The day Thomas came as my wingman and showed up forty minutes late. The girl ghosted me. I had spent two years believing I was just that uninteresting.

But thinking back on it now... the day he showed up late? He was wearing a brand-new jacket.

His hair was freshly styled.

He smelled like expensive cologne.

Who gets dressed to the nines just to play wingman for their buddy?

I dragged the data points across the screen, lining them up.

Out of the seven women, I could definitively place Thomas in the immediate orbit of four of them.

Always right after I walked away.

Always right after he promised he was just looking out for me.

I sat back in my desk chair, staring at the glowing mosaic of screenshots.

Outside, the city had gone completely dark.

I hadn't bothered to turn on the lights in my apartment.

A quiet, devastating thought bloomed in the back of my mind.

In ten years of friendship, Thomas had never posted a single photo of me on his social media.

Ten years. We were supposedly closer than brothers.

Not one photo.

I had scrolled through his entire grid. There were group shots with his coworkers, throwbacks with other college buddies, endless photos of his wife.

But no Daniel.

He had an excuse for it once. "Dan, you hate having your picture taken. Im just respecting your boundaries."

It was true. I wasn't big on photos.

But in a decade? Not even a candid?

I closed my laptop.

The apartment was suffocatingly quiet.

I could hear the slow, rhythmic thud of my own pulse.

Thump. Thump. Thump.

It was remarkably steady.

I wasn't consumed by fiery, blinding rage.

I just felt impossibly, hollowly cold.

3.

The next morning, I made a move.

I tracked down the phone number for Date Number Three. The tech girl. The one where Thomas was forty minutes late.

I sent her a text: Hey. I know its been years, but do you have ten minutes for coffee? I have a question about the day we met.

She replied almost instantly with a question mark.

Then she dropped a pin for a Starbucks near her office building.

When I walked in, she looked a little differenther hair was shorter, she looked a bit more tiredbut she carried herself well.

"What did you want to ask?" she said, taking a sip of her iced Americano.

"After that day at the bar... why did you completely ice me out?"

She blinked, genuinely taken aback.

"You really don't know?"

"Know what?"

"Your buddy," she said, setting her cup down on the wooden table. "The guy who showed up late. He added me on Snapchat before he left."

I stayed completely silent.

"He told me you had a severe history of mental illness. He told me to run while I could."

A laugh, sharp and jagged, scraped its way out of my throat.

"Mental illness."

"Yeah." She looked at me, her expression a mix of pity and lingering unease. "He said you were clinically unstable. That you had an ex-girlfriend, and when she broke up with you, you tried to slit your wrists. He told me he was doing me a favor, warning me. Said he was worried youd snap, so I shouldn't tell you we spoke."

I nodded slowly, letting the sheer magnitude of the lie wash over me.

"And then?"

"And then?" She offered a brittle smile. "Then I blocked your number. Whos going to take that kind of risk?"

I leaned forward. "Did he ever ask you out after that?"

She hesitated, her eyes dropping to the table.

"...Yes."

"How many times?"

"Three or four." She sighed. "Eventually, it gave me the creeps. He was way too aggressive about it. He didn't act like a guy who was just worried about his mentally ill friend."

I stood up, pushing my chair back.

"Thank you."

As I turned to leave, she called out, her voice tight. "Hey. Were you ever actually... sick?"

I looked back over my shoulder.

"What do you think?"

I walked out of the coffee shop and stepped onto the glaring, sunbaked sidewalk.

The heat was oppressive, but I suddenly felt the urge to throw my head back and laugh.

A history of mental illness.

Slit wrists.

The absolute audacity. The sociopathic ease of it all.

I pulled out my phone and started typing out messages to the others.

Number Four. Number Five. Number Six.

Not all of them replied.

But the two who did gave me the exact same missing puzzle piece.

Your buddy warned me.

The only thing that changed was the flavor of the poison.

For Number Four, the lie was that I was drowning in gambling debt and looking for a rich wife to bail me out.

For Number Five, the lie was that I had a deranged stalker ex-girlfriend who made my life a living hell.

I screenshotted every confession.

One image. Two images. Three.

The chain of evidence was growing heavy in my hands.

I leaned against a streetlight, staring at my phone screen.

Thomass WhatsApp profile picture was a minimalist illustration of a white lotus. Clean. Peaceful.

His bio read: Kindness is a choice.

I stared at those words until the letters blurred together.

Then I pocketed my phone and started walking home.

That was enough for today.

Tomorrow, I would dig up the rest.

4.

On the seventh day, I found the final piece of the puzzle.

It wasn't one of the ghosts from my dating history.

It was Thomass wife.

Megan.

I knew Megan. Sort of.

I had gone to their wedding. I slipped a generous check into a card for them. But I wasn't one of Thomass groomsmen. He had told me, looking deeply apologetic, that his younger cousin had begged for the spot and he couldn't say no.

I had clapped him on the shoulder. "Dont sweat it, man. Ill be in the front row getting all the embarrassing photos of you."

But I never sent him a single photo.

Because when I reviewed my camera roll the next morning, I realized every single picture of the altar was severely blown out and blurry.

Thomass cousin had teased me at the reception. "Damn, Dan, you're terrible with a camera."

I had just laughed it off.

Thinking about it now... the seat Thomas had explicitly reserved for me was directly in the glare of the stained-glass windows. Of course the photos were blown out. I was shooting blind into the sun.

Megan had met Thomas in 2019.

March 2019.

The date was burned into my brain, because that was the exact month of my very first setup.

The bank analyst.

I pulled up Megans Facebook page.