If You Date a Player, Should You Get Sympathy When They Cheat?

The Question That Won’t Sit Still

A friend of mine just left his partner for a younger woman—go figure. He’s a textbook narcissist and, truthfully, not a real friend so much as someone you tolerate because history made it awkward not to. And yet here I am, stuck in a moral grey zone: do I feel sorry for his wife?

I feel sorry that she’s hurting. I feel sorry that her life has been split in two by betrayal. But I’m conflicted because she pursued a player—the kind who goes to a club single and comes home with a plus-one, the kind who will flirt with your friend’s girlfriend if given half a chance, the kind everyone quietly warns you about. At his wedding, even the celebrant joked about it: how she was warned not to date him, how he was known for chasing, dating, ditching. They bonded over stories of the women he pursued. Red flags—served with champagne.

So now that he’s gone, wrapped up in a new romance, leaving devastation behind, the question lingers: if you knowingly date a player, should you get full sympathy when they cheat?

This isn’t a comfortable question. But it’s an honest one.

What Do We Really Mean by “A Player”?

A player isn’t just someone attractive or popular. A player has patterns. Patterns are repeated behaviours that continue regardless of who they’re with.

Common traits include:

• Serial short-term relationships

• A need for constant validation

• Boundary-blurring with others

• Charm without accountability

• A history that never quite changes

Patterns matter more than promises. When someone shows you who they are repeatedly, believing otherwise becomes a choice—often driven by hope rather than evidence.

Why People Still Fall for Players (Even When Warned)

From the outside, it’s easy to judge. From the inside, it’s rarely that simple.

The “I’ll Be the Exception” Trap

Psychology calls this optimism bias. We believe bad outcomes apply to others, not us. He cheated on everyone else, but he won’t cheat on me.

Validation Feels Like Value

When a player chooses you, it feels like winning a competition you didn’t know you entered. Being chosen feels like proof of worth.

Chemistry Is Loud, Compatibility Is Quiet

Players are intense. Intensity feels like connection. Stability can feel boring when you’re used to chaos.

When Red Flags Are Publicly Normalised

What struck me most about the wedding wasn’t the cheating—it was the laughter. The fact his behaviour was joked about, publicly acknowledged, and minimised.

When red flags are normalised, they lose urgency. When warning signs are laughed off, people stop trusting their intuition.

That doesn’t make future betrayal acceptable—but it explains how it becomes possible.

Cheating Is Still a Choice

Let’s be clear: cheating is not an accident.

• It’s not caused by temptation

• It’s not caused by dissatisfaction

• It’s not caused by the person who trusted you

Cheating is a decision rooted in entitlement. Players cheat because they believe they deserve more—more attention, more novelty, more admiration.

Nothing about being pursued excuses betrayal.

Why Sympathy Feels Complicated

This is where discomfort lives.

We instinctively want to comfort the betrayed. But when the betrayal feels predictable, sympathy becomes conditional.

People think:

• She knew what he was like.

• What did she expect?

• The signs were there.

But grief doesn’t operate on logic. Trauma doesn’t pause to check whether warnings were ignored.

The Difference Between Accountability and Blame

Holding someone accountable for ignoring red flags is not the same as blaming them for being hurt.

Accountability asks:

• What can be learned?

• What boundaries were missing?

• What patterns should not be repeated?

Blame says:

• You deserved this.

Only one of those is useful.

Society Is Harsher on Women Who Love Boldly

Women are often punished socially for choosing emotionally risky partners.

• Choose safe and you’re “settling”

• Choose exciting and you’re “naive”

Men who cheat are often expected. Women who are cheated on are analysed.

That imbalance matters.

Narcissism and the Illusion of Change

Narcissists are excellent at convincing others—and themselves—that they’ve evolved.

Marriage, babies, mortgages: these aren’t proof of growth. They’re milestones narcissists often use to stabilise admiration.

Change requires accountability, not applause.

Do You Get Sympathy?

Yes—for the pain

• Betrayal is traumatic

• Loss is loss, regardless of cause

• No one deserves deception

Less—for the shock

• Patterns repeat

• History matters

• Awareness changes expectations

Sympathy doesn’t have to be absolute to be real.

If You’ve Dated a Player and Been Burned

This isn’t about shame.

It’s about reflection.

Ask yourself:

• What did I ignore?

• What did I romanticise?

• What do I need to feel safe next time?

Growth isn’t pretending it didn’t happen. Growth is refusing to repeat it.

If You’re Watching This Happen to Someone Else

You can:

• Offer compassion without rewriting history

• Support without validating denial

• Be kind without being dishonest

Sometimes the most loving thing is saying, I’m sorry you’re hurting—and I hope you choose differently next time.

The Hardest Truth

Dating a player doesn’t mean you deserve betrayal.

But it does mean the ending wasn’t unforeseeable.

Both truths can exist without cruelty.

Where Sympathy Actually Belongs

Sympathy shouldn’t be rationed based on how perfectly someone loved. Pain doesn’t ask permission, and heartbreak doesn’t check your decision-making history.

But neither should we pretend that ignoring patterns comes without consequence.

The real lesson isn’t about who deserves sympathy. It’s about learning to stop romanticising people who show us—clearly—who they are. Love bravely, yes. But love wisely. And when someone’s behaviour is already written into their reputation, believe it.

Love Rubie xoxo