I Dated Four Girls at the Same Time — Here’s What I Learned

Let me start with a disclaimer: This is not a brag. This is not a guide. This is not a celebration of playboy culture. This is a story of emotional chaos, moral conflict, and a few hard-earned lessons about love, honesty, and the limits of modern dating.

The Beginning: Curiosity or Cowardice?

It started as an experiment—though calling it that feels disingenuous in retrospect. I was single, recently out of a long-term relationship, and deeply unsure about what I wanted. Dating apps gave me access to hundreds of profiles, and I found myself talking to multiple women at once. At first, it was innocent: casual chats, late-night banter, a few dates. But soon, it spiraled into something deeper, more complicated.

Before I knew it, I was dating four women simultaneously. And by “dating,” I mean regular meetups, shared emotional space, and in some cases, physical intimacy. None of them were told about the others—not because I was proud of keeping secrets, but because I didn’t know how to explain something I barely understood myself.

The Emotional Tangle

Each of these women brought something unique into my life. One was deeply intellectual—we could talk for hours about books and politics. Another was wildly creative, pulling me into a world of spontaneous adventure. The third had a grounded, nurturing energy that felt like peace in human form. And the fourth? She was fierce, ambitious, and reminded me of the parts of myself I was too afraid to embrace.

And yet, despite all this connection, I couldn’t give any of them the full version of me—because parts of me were constantly compartmentalized. I began lying. White lies at first: where I was, who I was with, why I couldn’t meet. But lies have a habit of multiplying. And with each lie, a part of me shrunk.

The Guilt That Follows You Around

Dating four women at once is not exciting—it’s exhausting. It’s waking up in the middle of the night with anxiety because you forgot which person you told what. It’s feeling a pang of guilt when someone says, “I’m really falling for you,” and you know you can’t say it back with the same weight. It’s having your phone on silent all the time not out of secrecy, but because the sound of a message bubble brings more panic than joy.

Over time, I started feeling less like a man with options and more like a fraud. I didn’t feel powerful—I felt hollow.

What I Learned About Myself

1. Validation is a Dangerous Drug:

I realized I wasn’t dating multiple women because I was searching for love—I was searching for validation. Each woman liked a different version of me, and I was intoxicated by that approval. I didn’t want to disappoint anyone, but in doing so, I disappointed everyone—especially myself.

2. Emotional Connection Isn’t Just Physical Proximity:

You can go on dates, hold hands, even sleep in the same bed—but if your heart isn’t truly present, it’s not a real connection. I was “there” with them, but not really with them.

3. Truth Is Harder, But Kinder:

The longer I delayed the truth, the more painful it became. Eventually, one of them found out, and the fallout was worse than I imagined. Not just because of the betrayal, but because they had genuinely cared. Being honest from the start—no matter how uncomfortable—would have saved a lot of pain.

4. We Often Confuse Options With Abundance:

Dating multiple people gave me options, but it didn’t make me feel full. If anything, it made me feel lonelier. Real abundance comes from being deeply seen and accepted—not from attention spread thin across different people.

The Fallout

When things collapsed—and they did, inevitably—it was brutal. There were tears, anger, confrontations, and silence. I lost the trust of people who had once looked at me with warmth. I also lost a bit of trust in myself.

But strangely, I also found something.

I found the courage to look at myself honestly. To admit that I had been scared of being alone. That I had confused attention for affection. That I had been selfish—not out of malice, but out of immaturity.

The Way Forward

Since then, I’ve changed the way I approach relationships. I don’t juggle people anymore. I’m clear about what I want, and if I’m unsure, I say that too. I learned to embrace the discomfort of honesty, because it builds something stronger than the illusion of charm—it builds trust.

I also learned that loving one person fully is far more fulfilling than charming four people halfway.

This isn’t a confession for sympathy, nor a cautionary tale soaked in regret. It’s simply a reflection. In a world where dating is often gamified—where “matches,” “likes,” and “situationships” blur the lines—it’s easy to lose sight of emotional integrity.

Dating four women at the same time taught me that it’s not just about who you date, but how you date. With intention. With honesty. And most importantly, with empathy—not just for others, but for yourself.

Because at the end of the day, love isn’t a game. And even if it were, the real win is finding peace within, not juggling players on the board.