Hannah Orenstein

My Mom Stalked My Crush On LinkedIn & He Noticed, Which Is Completely Mortifying

There's one cardinal rule when it comes to stalking the people you're dating: don't let them know you're doing it. You know it, I know it, everybody knows it... except for my mom, apparently. Once upon a mortifying time, my mom stalked my crush on LinkedIn, and he found out. Like, immediately.

During November of my freshman year of college, I was just starting to flirt with the idea of online dating. Browsing profiles online from the comfort of my own dorm room seemed way less intimidating than working up the courage to say hi to the hot senior in my humanities class. The first person who asked me out was this guy we'll call Will. Unlike me, Will was a capital-A Adult: he had just graduated from college the previous spring, he had a fancy job at an investment bank, and he lived in an apartment that didn't come with standard-issue twin XL beds. I was like, hi.

Our first date was at my favorite coffee shop on a crisp fall Saturday afternoon. I wore a glittery headband because Gossip Girl was still on TV and I hoped to subtly broadcast that I was a cool, sophisticated New Yorker, and not a transplant who had arrived here two months earlier. I had expected to make awkward chit-chat for 45 minutes over lattes, but we wound up hitting it off for hours. He was smart, thoughtful, and easy to talk to. Instead of a kiss goodbye, he went in for a nervous hug. Soon after, he texted to ask me out again.

We texted all the time — novel-length texts that required scrolling down to finish each one. I was giddy with anticipation. I had never felt so swept up by a guy who seemed to return my interest in him. So, even though we had only been on one date, I called my mom to tell her everything.

"And he does... what... exactly?" she asked.

I explained that it was something complicated (and probably kind of boring, TBH) at a bank.

"Which one?" she pried.

I told her the name.

"That sounds like an awfully big job for a 22-year-old kid. Are you sure he's not making that up?" she asked.

"Mom. He wouldn't lie. Who would do that? I saw him take a call on his BlackBerry. He seems legit."

"And what did you say his last name was?"

I told her. And then I gushed about how smooth and funny and charming he was, and how closely he had listened to me speak, and I forgot about her intense questions. It had been my first real, proper date ever — I didn't count the ones that revolved around making out in suburban minivans or eating dining hall food — and I had loved it.

For our second date, Will had made dinner reservations at an absurdly nice restaurant. I got sticker shock the minute I opened the menu. At first, I thought a $65 appetizer was the scariest thing I could imagine, but then the night took an even more terrifying turn.

"So, uh, I think your mom was stalking me on LinkedIn," he said, grinning.

"Uh. That sounds... possible," I admitted.

"Because you told her all about me?" he asked. "How much does she know?"

This was it. This was the moment I would lose my ability to appear chill and cool and casual in front of this guy that I was starting to really like.

"Well..." I began, nervously fidgeting with my napkin. "I guess I must have told her your name and where you work. And..."

I could barely make eye contact with him. It seemed like a faux pas, somehow, to admit that I liked him enough to tell my mom about him. But when I looked up, his face had gone pale. He was looking past my shoulder in horror.

"What's wrong?" I asked.

Suddenly, he looked embarrassed. "I told my friend I'd be here on a great date tonight," he muttered. "I didn't think she'd actually show up outside the restaurant to stalk us."

I whipped around in my seat and saw a dark-haired woman holding a camera dart past the restaurant's window.

So I wasn't the only overly eager one! I was flattered to hear that he confided in his friends about our date, and that helped me to realize that he probably didn't see my mom's stalking as lame at all — he took it as an encouraging sign that I truly liked him. That night, I learned that vulnerability isn't such a bad thing after all.

Will couldn't have been too weirded out by the incident, because we wound up dating on and off for the next few years. I think he took the whole thing really well because when you find real, sparkling chemistry, people's flaws and quirks fade away. They don't matter as much.

But since then, I've adhered to a strict policy of never telling my mom my dates' full names, workplaces, schools, or hometowns until I felt truly comfortable in the budding relationship — you know, just to stay safe.

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