Serial Dating After a Breakup: Why Attention Isn't the Same as Healing

After a breakup, have you ever found yourself jumping from one guy to the next, never really getting anywhere?

I have.

It’s a pattern I grew comfortable with starting in college. Back in the MiGente days (a social networking site for Latinos/Hispanics, kind of like Black Planet), I soaked up the attention. I met a lot of people, and I got good—really good—at juggling 3 to 5 guys at once.

I never mixed up their names. I always remembered where they were from. It became a game, and I was winning.

Eventually, I fell into my first serious, long-term relationship—and when that ended badly, I didn’t give myself time to mourn. I went right back into dating.

In Spanish, there’s a saying:

“Quitar una clave con la otra.”
(Replace one key with another.)

Basically: Find a rebound and move on.

Why I Did It

I know now that it wasn’t the healthiest way to heal. But at the time? It felt... convenient. I’d chat with someone online for a few weeks, meet once or twice, and move on.

I wasn’t sleeping with them all or falling for them. I just liked the attention. The distraction. The feeling of not being alone.

Among my girlfriends, it became a running joke. The men I dated even had nicknames because they couldn’t keep up with who I was talking to:
Snippy. Chicago. Boston. Masochist.

You get the picture.

The Truth About Serial Dating

It was less about romance and more about control.

If I didn’t get too close, they couldn’t hurt me.
If someone rejected me, I could quickly replace them.
All the perks, none of the risk.

My mom always told me,

“It’s not good to have so many eggs in your basket.”
But I didn’t listen.

Looking back now, I wouldn’t recommend serial dating to anyone who wants commitment. It’s fine when you’re young and figuring yourself out. But if you're genuinely ready to build something real? Serial dating is emotional avoidance wrapped in flirtation.

Yes, it gave me great stories (and blog material). But emotionally? It gave me very little.

Now, I’m Choosing Me

I recently made a promise to myself:

No more dating just to fill the silence.

I want to settle down. And that won’t happen unless I give someone the real opportunity to know me—and open up enough to know them in return.

It took me a long time to truly move on from my last relationship. But I did.

Now?

It’s time for me, myself, and I—the best relationship I’ve ever had.

Ugly Duckling Syndrome: Insecurity That Outlasts the Glow-Up

I’m not sure if this phrase has been officially coined, but a close friend and I use the term “Ugly Duckling Syndrome” to describe people who are attractive, smart, witty—and still suspiciously insecure.

They often grew up shy, awkward, overlooked, or in the shadow of a sibling who got all the praise. And while the glow-up may have come later in life, the emotional scars stuck around.

I didn’t realize how much this applied to me until a friend pointed it out. I tend to be unaware when someone is interested in me, and I often don’t recognize that I might be attractive in certain settings. Thankfully, I have amazing friends who lovingly slap some sense into me when I need it.

Dating With Ugly Duckling Syndrome

As I’ve dated older men, I’ve noticed this is something they pick up on quickly. Maybe it's because I spent years dating mimbos (you know the type—gorgeous, clueless, emotionally unavailable), and never had to face the full reality of being seen.

The thing about dating someone with Ugly Duckling Syndrome?
They’ll often deflect compliments, minimize their achievements, and joke away any attention.

My close friend—who I lovingly call my dating guru—once told me:

“Two Ugly Ducklings should never date. You need someone who sees you—even when you don’t see yourself—and pulls you up, not down.”

That hit me.

I’m confident in my career, my wit, my mind. But when it comes to physical confidence? I can be blind. And I’ve dated others who’ve been the same.

Case in Point:

I once dated a local amateur comedian—funny, charming, kind, and completely oblivious to the fact that women were clearly hitting on him after his sets.

He’d walk off stage, and I’d say, “You realize she was flirting, right?”
And he’d look at me blankly.

Don’t you know the best way into a woman’s heart (and maybe her pants) is to make her laugh?

Still, I loved watching him get attention.
It secretly boosted my ego.

“He’s going home with me,” I’d think, proudly.

But over time, I focused so much on propping him up, I stopped seeing red flags.
I lost myself.
The relationship became emotional—and exhausting.
And that’s another insecurity I’ll unpack in a future post.

It’s Not Just Me

I have a close friend who’s beautiful now—but she used to weigh 230 pounds in high school. She’s near 130 now, stunning, and still worries constantly about her weight.

Sometimes I just want to shake her and say:

“Look at what you’ve accomplished. Two kids, a full transformation, and you still look amazing. Be proud. Now get dressed—we’re going out.”

So If You Know Someone With Ugly Duckling Syndrome…

Don’t get frustrated. Just be present.
Sometimes all they need is someone to remind them who they are—until they finally see it for themselves.

Titles: When Labels in Dating Get Complicated

During my long, relaxing three-day weekend, I indulged in one of my favorite rituals—my own little Sex and the City marathon.

As I watched, something stood out: the women on the show would casually refer to men they’d only dated for a short while as their “boyfriend.”

And honestly? That baffled me a little.

I’ve always held titles in high regard. I thought most women did. Maybe it’s just me, but calling someone your boyfriend after a few dates seems... fast.

Then again, maybe it’s the show’s weird sense of time. Sometimes weeks pass between episodes, other times it feels like it’s all happening in a single day. It’s hard to tell what’s real.

So I started thinking about my own relationships—how quickly (or not) I’ve used titles in the past. I’ve seen relationships where two people fall fast and can’t live without each other. And I’ve also seen the opposite: a long courtship filled with uncertainty that never turns into anything more.

I’ve been in both.
And that long, drawn-out almost-relationship?

It ended in heartbreak.

There never seems to be a happy medium. And maybe that’s the point. Every situation, every connection, is different. Each one deserves to be treated as uniquely as the people in it.

After last year’s heartbreak, I’ve become much more cautious. I guard my energy more. I protect my heart.
But sometimes I wonder…

Should I be a little softer?
Should I stop overthinking and just enjoy the moment?
Should I go with the flow?

The truth is—who really knows?

What I do believe is that the best things happen when you least expect them. And yes, deep down, I still hope to be swept off my feet like one of the many romantic fantasies in my head.

Titles might not be so bad.
It’s the “L” word I’m really afraid of... 😅❤️

When Is It Too Soon? The Ongoing Question About Sex and Timing in Dating

I constantly seek advice from my friends—married, dating, or just very wise spectators—on how their relationships unfolded. One question I’ve been circling lately is:

When is it too soon to sleep with someone?

The inspiration? A TV show I love that, while a little dated now, still holds truths about dating that hit close to home.

So, I’ve started polling my friends. And the responses? All over the map.

From the Female Perspective:

For many women, it seems to come down to time.

“How long can you make him wait before he’s earned it?”
The most common answer?
A month.

But even that doesn’t quite make sense to me. What if you see each other 10 times in a week? Does that month still count? Does frequency matter more than the calendar?

Then there’s the question of emotional connection.
What should I expect in the meantime? Is there a checklist I’m supposed to mentally check off?
Honestly, I’m starting to think that many of us just want a measurable timeline—something to tell us we’re doing this “right.”

From the Male Perspective:

One guy told me the answer lies in how a man looks at you.

“When you know, you know—there’s something in the eyes.”

Another gave a more structured answer:

Three dates.
But, in his defense, those dates must be intentional—two people genuinely trying to get to know one another, not just filling time.

So... Is There a Right Answer?

With all this questioning, I’ve still come to no definitive conclusion.

What I do believe is this:
If you sleep with someone on the first date, in most cases, you might as well kiss the thought of a relationship goodbye and say hello to a situationship or a new friend with benefits. (Not always—but often.)

Then again, timing sex is a lot like trying to define love—no one formula fits all.

It’s messy. It’s gray.
And maybe that’s okay.

Lies, Secrets, and the Woman: Observations From the Last Single Friend

In a strange twist of fate, I’ve gone from being “one of the guys” to the only single girl among a circle of girlfriends in relationships. And with that shift came a whole new lens—one that sees the dynamics of love, lies, and lessons unfold in real time.

One of the biggest observations?

The evolution of a man’s behavior when he’s with a woman he loves.

I’ve come to believe that if men intentionally stepped into the “married mindset”—and yes, I’m putting “married” in quotes here—even early in the relationship, they’d be far more successful.

At first, they all swear:

“I’ll never change. I’ll always be me.”

But slowly, under a woman’s influence (read: wisdom and boundaries), they start to learn what not to do—aka, what won’t fly if they want peace at home.

Case in point:

I was recently on a trip where I overheard several guys chatting. The topic?

“What are you actually going to tell your partner about this trip?”

Most of them admitted they’d leave out a few details.
Except one.
One man said he planned to tell his wife everything—because in past relationships, he’d learned the hard way:

Secrets don’t stay secret.
She’ll find out.

And he’s not wrong.

The longer you’re with someone—especially as a man—the more your partner learns your tells. The shifts in your voice, the twitch in your face, the weird pause in your sentence.

Men are not subtle.
They aren’t built to hide emotions well.
They wear them on their sleeves—and honestly, they’re terrible liars.

I say this lovingly. I still have great friendships with these guys. But from where I’m sitting—on the sidelines of their relationship dynamics—it’s all just... comical.

Why do they think their secrets won’t come out?
And let’s be honest—men gossip more than women, but that’s a topic for another blog.

If (or when) their significant others find out what really happened?
Let’s just say... it’s going to be couch city, population: them.

The Mimbo: When the Chemistry’s There but the Depth Isn’t

Over the years, I’ve met plenty of men who carry the charming qualities of what some might call a “bimbo”—except in this case, the male version. Let’s call him what he is: a mimbo.

I recently encountered yet another one. Gorgeous smile, sculpted physique, and enough confidence to make anyone swoon. The attraction? Undeniable.

But then we had our first sober, non-belligerent conversation... and it hit me.

This man was not the brightest crayon in the box.

I tend to be sarcastic and quick-witted. It’s part of my personality—and frankly, part of my charm. So I find it oddly entertaining when a guy tries to keep up, misses the point, and still attempts to one-up me with lines that don’t land.

The moment I knew we were on different levels—intellectually and emotionally—was either:

1. When I told him we weren’t aligned, and he asked me to explain what “procrastination” meant.

2. Or... when he tried to introduce me to his parents in the first week of meeting.

Now don’t get me wrong—it’s refreshing to meet a man who’s emotionally open. But when it comes with zero self-awareness or discernment? Yikes.

And it made me wonder:

Is it that hard to put superficiality aside and find someone who actually gets you? Someone who fits your personality, not just your eye?

But then again... I’m fresh out of a tough breakup. And when you’re rebounding, maybe it’s okay if your rebound is ridiculously good-looking.

Just, you know—ask him not to talk too much.

Lessons Learned in Love: How Heartbreak Taught Me My Worth

Over the last year, life has taken me on an emotional rollercoaster—one that forced me to reassess what I truly want out of life and love.

There were moments where I felt completely lost, even though I was once so sure of the future I envisioned. I was living in limbo—reacting to life instead of creating it. The fog is just now beginning to lift.

My last relationship—if you can even call it that—was short-lived, but intense enough to leave a lasting impact. I’ve replayed every moment, every conversation, every red flag. And the conclusion I’ve come to is this:
I should’ve walked away the first time I felt doubt, instead of waiting for all hope to disappear.

Instead, I stayed. I overcompensated. I kept trying to prove my worth to someone who was too afraid to receive it. He was still wounded from a previous relationship. And in trying to avoid his pain, he created new wounds for me.

It was another tough lesson in the idea that rebound relationships rarely work.

And while I had never laughed so much or felt so connected to someone at first, I had to ask myself—was the emotional toll worth it?

A friend of mine once said,

“As a Gemini, you tend to dive in headfirst. You want to see the good in people. You give your heart before checking if it’s safe.”

And she’s right.

But the last two experiences taught me to pause. To breathe. To see the bigger picture, not just the hopeful potential. Most importantly, they taught me this:

Knowing your self-worth is everything.

When you know your value, you stop chasing people who can’t see it. You stop trying to prove yourself to someone who should’ve known your worth from the start.

Yes, the pain will fade. But the memory of it will linger—just long enough to protect me from repeating the same mistake.

Unfortunately, heartbreak often builds walls. The next person will likely face those walls. But maybe that’s not a bad thing. Because the right person won’t run from them.

They’ll see the walls... and think you’re worth climbing over them.

Unnecessary Advice: When a Friend Crosses the Line

Last night, I went out with a couple of friends—one of whom I’ve known for quite a while. During our conversation, my current engagement came up. This friend, like my fiancé, holds more conservative views about friendships and boundaries.

The tension began when I referenced his past behavior—specifically, a few moments when he was belligerent. He didn’t appreciate that I shared those examples in front of others. As a schoolteacher, he felt those stories reflected poorly on him. He asked me to be more discreet around people he didn’t know well. I understood, apologized, and took his request seriously.

But then the conversation took a turn.

He began offering me relationship advice—advice I hadn’t asked for. He told me I shouldn’t be so open with my fiancé about my “questionable past,” referencing things I’ve written about in my blogs. He said, “What he doesn’t know won’t hurt him.”

I disagreed. Strongly.

To me, honesty builds trust. I’d rather be sincere and open now than have my partner find out something later and feel betrayed. That kind of dishonesty can wreck a relationship far more than the truth ever could.

We went back and forth for two hours.

He insisted I wasn’t listening. But I was—I just didn’t agree. I’m more liberal in my communication style. My relationship has weathered both lows and highs. We’ve grown because of our openness. So when he generalized all relationships as being “the same,” I pushed back again.

Not all relationships are the same.

Yes, we all have goals, and yes, we might face similar situations. But how we navigate them? That’s unique. Sometimes past conversations surface through direct questions. Other times, they come up organically. Maybe he read something I wrote. Maybe I asked. Maybe he did.

The point is: I didn’t ask to dissect my relationship. I didn’t ask for advice. And honestly, his feedback felt more like a lecture than a conversation.

I finally told him that certain things within my relationship are private. He doesn’t know the full picture. He has no right to advise me on something he doesn’t understand—especially when, by his own admission, he struggles to maintain relationships himself.

Yes, I can be stubborn—but I also listen. I’m not above asking questions or seeking guidance when needed. But don’t force your opinion on me and expect me to parrot it back like a student. Don’t change your stance mid-point just to win a debate.

I get it.
I just don’t agree.

If I ever need advice, I’ll ask. But I won’t ask a professional swimmer how to play football.

Have you ever received unwanted relationship advice from a friend? How did you handle it? Share your thoughts in the comments.

The Younger Man: Why I Trust My Experience Over Empty Promises

When I meet someone new, I try to give them the benefit of the doubt. After all, I don’t know their habits, their story, or what they've been through. But that doesn’t mean I let all my walls down. I keep my guard up and only reveal just enough of myself—especially when it comes to younger men.

They always say the same thing:

“You’re different.”

And every time, I choose to give them a fair shot. I allow them the space to pursue me—to show me they’re serious. But the truth is, I’ve never been proven wrong from my original theory:

A younger man will always be a younger man.

Now, don’t get me wrong—I’m not saying this from a place of ego or superiority. But I’ve lived through some hard things. Life has matured me in a way that most 24-year-olds haven’t had to experience yet.

I observe my surroundings carefully. I practice patience. And one of the things I can’t stand is when someone denies what I clearly see. Younger men often feel that admitting the truth is giving up power, when in reality, acknowledging the truth now prevents problems later.

And so, until someone proves me wrong, I’ll keep living by this belief.
Because patterns don’t lie.
And neither does intuition.

Have you dated someone younger than you? Did they prove your assumptions right—or surprise you? Let’s talk about it in the comments.

My Worth

In a brief conversation, a man asked a woman he was pursuing the question "What kind of man are you looking for?" She sat quietly for a moment before looking him in the eye and asking "Do you really want to know?" Reluctantly, he said, "Yes." She began to expound... As a woman in this day and age, I am in a position to ask a man what he can do for me that I can't do for myself. I pay my own bills. I take care of my household without the help of any man...or woman for that matter. I am in the position to ask, "What can you bring to the table?" The man looked at her. Clearly he thought that she was referring to money. She quickly corrected his thought and stated, "I am not referring to money. I need something more." I need a man who is striving for perfection in every aspect of life." He sat back in his chair, folded his arms, and asked her to explain. She said, "I am looking for someone who is striving for perfection mentally because I need conversation and mental stimulation. I don't need a simple-minded man." I am looking for someone who is striving for perfection spiritually because I don't need to be unequally yoked... believers mixed with unbelievers is a recipe for disaster. I need a man who is striving for perfection financially because I don't need a financial burden. I am looking for someone who is sensitive enough to understand what I go through as a woman, but strong enough to keep me grounded. I am looking for someone who I can respect.In order to be submissive, I must respect him. I cannot be submissive to a man who isn't taking care of his business. I have no problem being submissive...he just has to be worthy. God made woman to be a helpmate for man. I can't help a man if he can't help himself. When she finished her spill, she looked at him. He sat there with a puzzled look on his face. He said, "You're asking a lot." She replied,"I'm worth a lot."..> Thank you Helena!