What I Learned From Dating in My 20s
Dating in your twenties is like going to a buffet blindfolded—you’re hungry, hopeful, and occasionally end up eating something that makes you question your entire existence. I walked into that decade wide-eyed, full-hearted, and absolutely clueless. I thought love meant sacrifice. I thought red flags were cute little quirks. I thought calling off a wedding three weeks before the big day would ruin me.
Spoiler alert: it didn’t. It saved me.
Here’s a not-so-glamorous list of what I learned through trial, error, and one too many emotionally unavailable men.
1. Calling Off a Wedding Isn’t Failure—It’s Freedom
Three weeks before I was supposed to say “I do,” I said “I can’t.” And that was the most honest thing I’d done in years. I had confused love with loyalty. I thought staying was noble. But deep down, I knew I wasn’t marrying a life partner—I was marrying someone who made me feel small, anxious, and exhausted. Calling it off didn’t make me broken. It made me brave.
2. Short-Term Flings Can Be Sweet... Until They’re Not
Sometimes it’s magical for a month. The thrill, the touch, the passion. But when the dust settles, you realize you barely know the person—or worse, that you do know them, and wish you didn’t. Short-term flings taught me to stop romanticizing people just because they made me laugh or looked hot in a leather jacket.
3. Long-Term Doesn’t Always Mean Long-Term Growth
I’ve been in relationships that lasted years and went nowhere. Staying with someone out of comfort or shared history is like wearing a pair of shoes two sizes too small—you’ll get used to the pain, but eventually, you’ll start limping through life. Long-term doesn’t mean they’re your person. It just means you stayed.
4. Dating a Mama’s Boy Requires a Third Chair at the Table
I dated someone who consulted his mom on everything—from what shirt to wear to what career to take. It was less of a relationship and more of a three-person group chat I never asked to be part of. Respecting your mom is beautiful. Being emotionally enmeshed with her is... not.
5. Some People Hide Who They Are Online—$10,000 Deep
Yes, I dated someone who secretly spent over $10,000 on cam sites. With men. And women. And a lot of shame. What I learned? Secrets always find the light. And no amount of love can rescue someone from their own self-deception if they’re not ready to face it.
6. I Hate Kissing a Man After He Eats Spaghetti
I don’t care how good your bolognese is. That acidic, tomato-basil residue lingering in your mouth is an instant no. Some things you don’t know about yourself until you’re grossed out mid-kiss. This was one of them.
7. Some Men Just Want Sex
Not connection. Not depth. Not conversation. Just access to your body. And they’ll charm their way through it—until you notice their words are empty and their attention span ends at the edge of your bed. That’s not intimacy. That’s consumption.
8. Others Want Emotional Connection... But Can’t Hold It
Some men crave deep connection but collapse under the weight of vulnerability. They’ll ask you how you’re feeling but flinch when you cry. They’ll want you to understand them but never truly open up. These relationships left me lonelier than being alone.
9. Misogyny is Alive and Wearing Cologne
I’ve dated men who believed a woman’s place was in the kitchen. Who made jokes at my expense. Who thought “emotional” was an insult. Who called themselves “protective” but acted controlling. These men didn’t need girlfriends—they needed therapy and a reality check.
10. Some Men Want to Impregnate You After One Date
I wish this was a metaphor. It’s not. There are men out there who will talk about baby names before they even know your middle name. Beware. It’s not romance—it’s often control, insecurity, or worse, an attempt to tether you to them permanently.
11. Mental Health Scares the Wrong People Away
I live with mental health struggles. I’m open about them now, but back then, I tried to hide them. I learned that most men weren’t running from me—they were running from the responsibility of empathy. If someone can’t handle your darkness, they don’t deserve your light.
12. Not All Men Pass the Penny Test (Yes, My Dog)
If you want to know who someone really is, watch how they treat your dog. My dog, Penny, has a sixth sense for red flags. If she growled, backed away, or didn’t want to cuddle up, I should’ve listened. The men who loved her—and let her be the weird, wiggly, attention-demanding queen she is—were few and far between. But they taught me more about character than a hundred dinner dates ever could.
In the End…
My twenties weren’t a string of failed relationships—they were a crash course in boundaries, self-worth, red flag detection, and emotional intelligence. I learned that love doesn’t mean fixing someone. That chemistry isn’t compatibility. That my gut is smarter than my heart sometimes.
And maybe most importantly: I learned that I'd rather call off a wedding than live a life that isn’t mine.
Here’s to the next decade—wiser, wilder, and way more selective.
If you’ve been there—dating disasters, red flags, or called off your own almost-ever-after—drop a comment or message me. I’m building a community where we can laugh, cry, and heal through our love stories. The messy ones included.
- Devon (& Penny)
