I went on my first date with my coworker, Mari, and everything was perfect, until the bill came. I checked my pockets and realized my wallet was gone, but Mari stayed totally cool and covered dinner. But the next day, I found out she sent me a Venmo request for exactly $47.83.

Not $48. Not a clean $50. No “don’t worry about it.” Just a blunt, emotionless $47.83 with a pizza emoji and the words “last night.” I stared at the notification for like five minutes straight, unsure whether to be embarrassed, annoyed, or just laugh.

Thing is, Mari and I had been work friends for a few months. We’d grab coffee after meetings, exchange memes, vent about our manager in low whispers in the hallway. She had this dry, slightly chaotic sense of humor that I liked. And I’d had a rough breakup the year before, so I wasn’t exactly jumping into the dating pool again—but Mari made it easy.

So when we finally went out, I thought it was going somewhere.

That night was fun. We shared a large Neapolitan pizza, split a bottle of wine, and even had tiramisu, which she insisted on ordering “because life is short and so am I.” She laughed at my jokes, complimented my playlist on the drive there, and didn’t flinch when I told her about my failed move to Chicago. It felt real. Comfortable.

Which is why the cold little Venmo request hit so weird.

I figured I’d just ask her about it, keep it casual.

At lunch, I nudged her playfully and said, “So… you’re really gonna invoice me for dinner like we’re contractors?”

She didn’t laugh. She just shrugged and said, “Yeah, I don’t do the ‘guy pays for everything’ thing. Fair’s fair.”

I didn’t know what to say to that. I wasn’t expecting her to cover it all—I’d just lost my wallet. But it also wasn’t about the money. It was the tone.

It felt transactional.

Still, I respected it. She was principled. Independent. Maybe that was a good thing.

I paid the $47.83. Added a pizza emoji back. Moved on.

But something shifted after that. I started noticing how… precise Mari was about everything. She’d bring her own mug to work because she didn’t like washing communal ones. She tracked every dollar of our shared Lyft rides to off-site meetings. And one time when we got lunch with our team and the bill got split evenly, she asked the waiter to adjust it because she didn’t get a drink.

And don’t get me wrong—everyone’s got a budget. I totally get that. But Mari made me feel like I was in some kind of financial spreadsheet every time we hung out.

Still, I liked her. And I thought maybe I was just being sensitive.

So we went on a second date.

This time, I triple-checked for my wallet. We went to this little Korean BBQ spot she picked, and I made sure to insist, multiple times, that I was covering it. She let me, with a tight smile.

Back at her place, we watched a documentary, shared a blanket, and it felt easy again. She rested her head on my shoulder and whispered, “You’re not like the other guys here.” I asked her what she meant.

She said, “They all flex. Brag about their cars and crypto wallets. You’re just… normal. It’s nice.”

That stuck with me.

Maybe I’d been too hard on her. Maybe she just had walls. I get that. We all do.

But then came the third date. And that’s when things unraveled fast.

I invited her to my place. Cooked dinner—shrimp linguine, garlic bread, a little salad. She brought over a bottle of red. Everything felt laid-back, warm.

Until she asked to use the bathroom and came out holding a small envelope.

“This yours?” she asked, holding it between two fingers.

I blinked. “Yeah… it’s rent money. I was gonna deposit it tomorrow.”

She smiled, but not in a nice way. “Cash, huh?”

I didn’t like her tone. “Yeah. My landlord’s old school.”

She nodded slowly. Then asked if she could crash at my place the next weekend since her apartment was getting fumigated. I said of course.

But the next morning, the envelope was gone.

At first, I thought maybe I moved it. I looked everywhere—drawer, coat pocket, under the bed. Nothing. My stomach dropped. That was $1,200 in cash.

I texted Mari:
“Hey, super awkward but—did you see an envelope near the TV? My rent money?”

She replied:
“Nope. That sucks. Maybe check the fridge lol.”

Fridge? That felt off. I tore the place apart. No envelope.

I didn’t want to believe it. I couldn’t believe it. But that was the only time anyone else had been in my apartment.

And there was no sign of forced entry.

Still, accusing someone of stealing is huge. I didn’t say anything more. Just borrowed from my savings and paid the landlord. Told myself I was being paranoid.

But two weeks later, something happened at work.

Our office had a small wellness fund. $200 a month to each employee for gym memberships, yoga classes, therapy—whatever. You had to submit receipts through an online portal. One afternoon, I got a call from HR saying my submission for “Mindful Balance Yoga” had already been reimbursed.

I hadn’t submitted anything yet.

When I checked the system, someone had uploaded a receipt in my name. Same yoga place Mari went to. Same date she was off work.

It wasn’t my handwriting. But it was my name, my employee ID.

That’s when I realized I’d left my laptop open around her. She knew my password—I’d told her once when she helped me upload a work file.

I went cold.

I didn’t want to believe it. Not Mari. But there were too many coincidences stacking up. Too many moments that now looked completely different in hindsight.

I didn’t go to her directly.

Instead, I walked into HR the next morning, explained what I’d found, and asked them to investigate quietly.

They said they’d look into it.

Three days passed. Then Mari didn’t show up for work. Not a text, not a call. Just… gone.

The following Monday, our manager called an all-staff meeting and said Mari had “resigned for personal reasons.” No one asked questions. But I saw two of the HR reps exchanging looks across the room.

Later that day, I got an email confirming I’d been reissued my wellness funds. The duplicate claim had been flagged and removed.

They didn’t say who submitted it.

But I knew.

I thought that was the end of it. I figured Mari had cut ties and moved on.

Until about a month later, I got a friend request on a new Instagram account. No profile pic. No posts. But the name was a jumble of letters that looked… vaguely familiar.

The first message said:
“You didn’t have to snitch.”

Then, a few minutes later:
“I only took what was fair.”

I blocked the account immediately. My hands were shaking.

I didn’t tell anyone. Not right away. I just kept my head down, worked, and tried to forget.

But a weird thing happened over the next few weeks.

I started hearing little stories around the office. About how Mari had borrowed money from a few coworkers “just till Friday.” How she used the same bottle of kombucha to fake three different wellness claims. How she once got caught copying code from someone else’s laptop and tried to blame the intern.

I hadn’t been the only one.

One day, months later, I ran into Saida—one of our coworkers—in the break room. She looked at me and said, “You were the first one she actually got close to. Sucks that it ended like that.”

I nodded. “Yeah.”

Then she said something that stuck with me: “Some people treat kindness like a weakness. But it’s not. It’s a mirror.”

At first, I didn’t get it. But I thought about it a lot.

Mari saw people who helped her and thought: Suckers. She saw trust and saw opportunity. But in the end, all it did was leave her alone. She burned bridges so fast, there was no one left on the other side.

It took me a while to stop feeling stupid. To stop replaying that night with the missing envelope. To stop wondering if I could’ve handled it better.

But eventually, I realized something.

I hadn’t been dumb. I’d been open.

And yeah, it came back to bite me—but I’d rather be someone who gives people a chance than someone who plays life like a game of chess, always waiting to take.

Funny thing is, a few months after all this, I met someone new. Her name’s Noor. She works in community development. Kind, hilarious, asks real questions and actually listens.

On our first date, she offered to split the bill. I said, “Nah, I got it.” She smiled and said, “Cool. I’ll get dessert.”

We’ve been doing that ever since.

One person covers, the other brings balance. No spreadsheets. No invoices. Just… give and take.

Exactly how it should be.

Sometimes the best lesson comes wrapped in the worst experience. What Mari did wasn’t okay—but it reminded me to trust my instincts, to pay attention to patterns, and to never let one broken person harden my heart.

If you’ve ever had someone betray your trust, you’re not alone. Just don’t let it change your kindness—only your boundaries.

If this hit home, like and share. Someone out there might need to hear it today.