My date from HELL

This happened when I was 26!

I went on one date with a 36-year-old, and that’s when I learned to date guys within three years of my age. I didn’t know much about him until we met, and I was still pretty naive about the online dating world.

For context: at the time, I had a master’s degree, a car, and a job.

As for him: by 36, he was divorced, had no post-secondary education, and technically couldn’t work—but he was a part-time real estate agent. He had been hit by a car at 32 and was living off a settlement. He told me that by 40, he’d be getting his pension early.

If that wasn’t already a red flag 🚩, here’s what he did during the date that absolutely pissed me off:

1️⃣ He was on his phone and shushed me before I could even introduce myself. I sat there for 5 minutes waiting for him to finish whatever he was doing—apparently a “flex” about his career.

2️⃣ He never picked up on how uncomfortable I was. He dominated the conversation, talking endlessly while I just sat and listened.

3️⃣ He bragged about not needing to work because he was “set for life” after his accident. Then he shared that his mom worries about gold diggers, and casually implied I was one because he bought me a $7 coffee.

4️⃣ He flexed about owning five properties and asked if I wanted to tag along while he collected rent from tenants… during the date.

5️⃣ He mentioned he only sells about three houses a year but “technically doesn’t need to work.” (I don’t even know if that’s good or bad.)

6️⃣ When I asked about his education—because his profile claimed he was a real estate lawyer—he completely lied about his degree and gave a BS answer.

7️⃣ When he told me he was divorced, he said the nastiest things about his ex-wife and overshared about their sex life… to a complete stranger (me).

8️⃣ He asked me to pull out my phone so he could look through it (!!), probably to check if I was talking to other guys. I didn’t show him, obviously.

9️⃣ Because I was younger, he dismissed everything I said as childish and gave unsolicited “life advice” about my personal affairs.

The date ended when one of his tenants called him to collect rent urgently. He said he didn’t want to leave me, but I quickly said, “Oh yeah, you should go!” As soon as I got out of the cafe, I was jumping for joy.

Did I block him after the date? No (ugh, rookie mistake). He texted me asking for a second date, and when I politely declined, he sent a follow-up message pretending to “want to learn” why I didn’t want to see him again.

Here’s what I learned from that guy:

• He’s messy.

• He’s the worst.

• That follow-up message wasn’t about learning—it was about getting a second chance, defending himself, or snapping at me.

• Guys like this will never learn.

• He’s probably going to die early from stress and bitterness.

• RUN 🏃‍♀️

• Always block guys like this after the first date.

• Never reply or say anything that might instigate problems.

• He is unhinged.