Wednesday, January 28, 2026

Sex and the Suburbs – Holly reckons men should pay, women, too

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Join Holly as she searches east Auckland for love and connection.

In which Holly reckons men should pay… and women, too.

Who should pay on a date, the man or the woman? This was the question recently posed to me, Reader, by a newly single friend.

Let’s start with first dates. Usually, these won’t be a fancy dinner – just coffee or a casual drink.

For those, I think it’s important that each party covers their own.

If you’re having a fabulous time, you can always offer to grab the next round.

Pay-as-you-go leaves space for that possibility, but it also allows both parties the opportunity for a hassle-free exit if the vibe isn’t right.

On subsequent dates (if you’re open to building a future with someone) other considerations come into play.

During those first rosy months of courtship, a potential partner will be actively trying to demonstrate they can show up well for you.

If they’re underinvested now, you might naturally wonder about how things would be in a year… or 10.

In my opinion, this question isn’t actually about money or gender.

It’s about communication. Can you both communicate calmly about what works for you, and what’s fair?

In the longer term, finances are a major stressor in many relationships. Are you capable of getting on the same page?

While the conversation might be awkward, it could be a good early litmus test for how you both set boundaries or compromise.

As someone who’s hyper-independent, I generally prefer to pay my own way.

I stubbornly insisted that my deep-pocketed ex should never buy me anything.

He argued that he enjoyed treating me to fine things… he’d worked hard for his fortune and should be able to spend it how he wanted.

During those first rosy months of courtship, a potential partner will be actively trying to demonstrate they can show up well for you. Photo supplied Unsplash.com Priscilla Du Preez

For a while, neither of us understood why the other seemed so intent on making things difficult.

In the end, we both learned something about acceptance.

Instead of me focusing on independence, and him focusing on generosity, we both agreed to give a little, and simply focus on enjoying our time together.

That’s the thing about compromise – sometimes, you just have to let someone love you in ways you don’t fully understand.

Then, there was the guy who waved me off as I tried to pay my share of our third date.

His voice dripped with disdain as he informed me that, as a gentleman, payment was his domain. There was to be no conversation.

He acknowledged that women often invest more time, money and energy before the date even starts, just to look “presentable” and keep ourselves safe getting there and back.

I appreciated his understanding this, and his paying for dinner, but I didn’t appreciate the disdain – nor the ungentlemanly assumption, later on, that I’d go to bed with him.

When I refused, he accused me of just being there for the free dinner.

Occasionally, Reader, chivalry is just chauvinism dressed up as kindness.

This is where tradition does a number on us all. For generations, fairytales taught women that all they needed to do was be pretty and wait for their prince to come.

At the same time, patriarchal ideals clamped the lid of the ‘Man Box’ down tight, teaching men that one of the only ways for them to show up in a relationship was as the provider.

For some, those generational teachings might take time to dismantle.

In the meantime, the accepted etiquette seems to be that the person who suggests the date should pay for it, but the other party should offer to chip in.

Share your thoughts! Email holly@times.co.nz

Yours in love,

Holly

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