Why Should Men Always Pay For Women

Why Should Men Always Pay for Women?

I used to be that guy who always insisted on paying. Always. It was part of my identity, woven into my understanding of what it meant to be a “gentleman.”

But an experience last month completely shifted my perspective on this age-old dating custom.

The Night That Changed Everything

It was a regular Friday night at an upscale restaurant. I was on a third date with Sarah, a successful software engineer. When the check arrived, I did my usual reach for the wallet, but what happened next sparked a conversation that made me question everything I thought I knew about dating dynamics.

Like many men, I was raised with certain beliefs:

Men should always pay

It’s a sign of chivalry and respect

It shows you can provide

It’s what a “real man” does

I never questioned these assumptions. They were as natural as holding the door open or pulling out a chair.

Sarah put her card down firmly and said something I’ll never forget: “I respect you, and I want you to respect me as an equal. Letting you pay for everything doesn’t feel right to me.”

This wasn’t about money. She continued, “When one person always pays, it creates an unspoken power dynamic. Is that really what we want in modern relationships?”

The Uncomfortable Truth

As we discussed it further, I realized several things:

1. Always paying can create unhealthy expectations
2. It can make both parties uncomfortable
3. It doesn’t reflect the reality of modern relationships
4. It can prevent genuine connections based on equality

In 2024, when women are CEOs, doctors, and leaders in every field, why do we cling to a custom from when women couldn’t even have bank accounts? Some of my dates earned more than I did. The assumption that men should always pay suddenly seemed not just outdated, but potentially offensive.

A Better Approach

What I’ve learned is that it’s not about who pays — it’s about mutual respect and open communication. Here’s what works better:

• Discuss expectations openly
• Take turns paying
• Split bills when it feels right
• Focus on creating experiences together rather than transactions
• Let the relationship dynamic evolve naturally

The Modern Reality

The truth is, healthy relationships are partnerships. They’re built on:

• Mutual respect
• Shared responsibilities
• Open communication
• Equal contribution (in various ways)
• Trust and understanding

Now, when I go on dates, I have a different approach. Instead of automatically reaching for the bill, I’m open to conversation about it. Sometimes I pay, sometimes she pays, sometimes we split it. And you know what? It feels more genuine this way.

The question shouldn’t be “Why should men always pay for women?” but rather “How can we build genuine connections based on equality and mutual respect?” The answer might be different for each couple, and that’s okay.

What Really Matters

At the end of the day, what makes a relationship special isn’t who pays the bill — it’s the connection between two people who respect each other as equals.