What I Learned From Dating 100 People in 30 Days

It started as a joke.

I was sitting with two friends, glass of wine in hand, licking my wounds from yet another failed “situationship.” Somewhere between sarcasm and sadness, I muttered, “Maybe I should just date a hundred people and see what sticks.”

They laughed. I didn’t.

Later that night, I opened a fresh spreadsheet, redownloaded five dating apps, and drafted a plan: 100 first dates in 30 days. That meant at least 3–4 dates per day, no repeats, no flaking, no ghosting. I wasn’t looking for the one. I was looking for… something. Closure? Chaos? Clarity?

I got all three—and more.

Week One: Curiosity, Cocktails, and Crashing Apps

The first week was exhilarating.

Everyone seemed excited by my challenge. Some dates turned into mini-interviews, others into real conversations. One guy brought me a tiny succulent as a gift. Another girl invited me to her improv class that night. I met a med student who talked about brain surgery like it was tying shoelaces. A stand-up comedian made me laugh so hard I nearly spilled my drink.

The variety was intoxicating: poets, programmers, polyamorous vegans, conspiracy theorists, startup founders, quiet introverts, loud extroverts, and one person who refused to give their last name “for legal reasons.”

But by day five, the shine was already starting to fade.

Week Two: Red Flags and Repeat Questions

“How many siblings do you have?”

“What do you do for work?”

“Where are you from originally?”

If I had a dollar for every time I answered those questions, I could’ve paid for therapy. And I needed it.

By week two, the novelty wore off and the emotional fatigue set in. I felt like a badly programmed chatbot—saying the same lines, forcing smiles, scanning for exits.

One man brought his mom. Another asked if I had “childbearing hips.” A woman tried to convince me that birds aren’t real. I met someone who smelled like regret and another who openly admitted to stalking their ex—on the first date.

I realized something: dating is less about finding compatibility and more about filtering chaos. But even in the weirdest moments, there were surprises.

A woman shared a poem she wrote about her sister’s passing. A nonbinary artist showed me their sketchbook full of raw, beautiful pain. A man recited an entire monologue from The Lord of the Rings without breaking eye contact. Somehow, I didn’t hate it.

Week Three: Breakdown, Breakthrough

Around day 20, I had my first breakdown.

I was exhausted—mentally, physically, emotionally. I was overcaffeinated, underslept, and losing myself in the process. My friends joked I had a new identity: “DateBot3000.” I smiled, but I wasn’t okay.

One night, after a particularly awkward dinner with someone who spent 45 minutes talking about cryptocurrency and refused to split the bill, I sat in my car and cried. Not because of the date. Because I realized I was chasing something I couldn’t name—and it was hollowing me out.

So I changed the rules.

I stopped pretending. I ditched small talk. I started asking real questions:

What are you afraid of?

Who broke your heart?

What does love mean to you?

Shockingly, many people responded in kind. A single mom told me about her postpartum depression. A man admitted he’d never been in love. One woman shared how she got sober and rebuilt her life from scratch. Those moments felt more real than anything I’d experienced in my past relationships.

I started feeling human again.

Week Four: The Ones I Remember

Of the 100 people I met, most blur together now. But a few stand out.

The teacher who told me, “Every kid just wants to be seen. Adults too.”

The shy barista who said almost nothing but smiled like he meant it.

The woman with anxiety who trembled the whole time and still showed up.

The guy who told me I reminded him of his late sister—and somehow, it didn’t feel weird, just deeply human.

There was also one person I almost broke the rule for. We clicked instantly. Conversation flowed like water. We laughed until our stomachs hurt. As we walked to our cars, they said, “I wish we had more time.” So did I.

But I stuck to the plan.

What I Learned

Dating 100 people didn’t lead to love. It led to something more valuable: understanding.

I learned that attraction is unpredictable. That kindness is rare, but unforgettable. That most people are lonely, even the ones who pretend not to be. I learned that vulnerability scares people—but also connects them in profound ways.

I discovered I had patterns. I chased emotionally unavailable people because it felt familiar. I dismissed quiet, stable ones because I mistook peace for boredom.

Most of all, I realized how little time we spend really listening—to others, and to ourselves.

Final Thoughts

Would I recommend dating 100 people in 30 days?

No.

Would I do it again?

Absolutely not.

But would I take back the experience?

Not for a second.

Because somewhere between the worst date of my life and the most unexpectedly beautiful five-minute conversation, I found something I didn’t expect to find: myself.