Who pays on a date in 2025?

Confession time: dating over 60 is a bit like going back to high school, only your knees hurt and you actually like brussels sprouts now. But some questions, it seems, never go out of style – like the eternal conundrum: who’s meant to pick up the tab?

Just ask Trevor. Yes, Trevor, 69, freshly widowed and daring enough to update his profile photo for the first time since the invention of the digital camera. He met Jenny at a wine bar in the city, well-reviewed on Google and mercifully not too loud.

They laughed, they talked about European bus tours and their shared horror of reality TV. Trevor, ever the gentleman, ordered two glasses of pinot noir. “I paid for them both,” he reports, with the faintest trace of wounded pride. “And after two hours of sparkling conversation – I didn’t even get a kiss on the cheek!”

So, who should pay on a date these days?

Is it always up to the gentleman, as some old school etiquette used to say? Or, in this modern age – when Jenny might have a bigger super balance than Trevor, or more property or shares – should women reach for their purses, too? Surely we’ve moved past the days of gendered wallet-opening? Or… have we?

Times have changed, my friends, but awkwardness persists. In our twenties, splitting the bill or “going Dutch” was often the go-to, especially as everyone was broke and buying fancy coffee was an indulgence. Fast-forward to your sixties: the hair may be greyer but the stakes are surprisingly similar – because, let’s face it, no one wants to look stingy, and no one wants to feel sold.

Here’s the rub: by the time you’re 60, both parties might be very comfortably off. Maybe you both have well-fed offset accounts. Maybe, for the first time in your adult lives, you’re not waiting for payday to buy a new shirt. Does that mean the old rules are silly? Or is there a chivalrous pleasure in a man buying the drinks, or a woman insisting, “Next round’s on me”?

Trevor’s friends (a lively bunch at bowls on Tuesday morning) are split. Half say, “Of course you pay, mate, that’s how we were raised!” The other half, including Glenys who spent 35 years running her own business, says, “Why should the bloke always pay? I’ve got plenty myself, thanks very much.”

Jenny, for the record, called Trevor a “lovely man” but told her girlfriend she didn’t like the pressure of a ‘return on investment’ – at least, not after two pinots and a first meeting. “I’d have felt better if he at least let me shout a second round. It’s just drinks, not a down payment on a relationship.”

So here’s my advice, dear daters:

• Don’t expect anything for a glass of wine. It’s an ice-breaker, not a contract.
• Talk about money, even in small ways. “Shall we split this, or would you like to swap next time?” is honest and surprisingly charming.
• Notice if someone genuinely wants to pay. Sometimes, paying is about generosity and joy, not power or expectation.
• Don’t keep score – romance is not a ledger. But also, don’t be afraid to reach for your purse or wallet, even if you’re used to other people paying.

Dating after 60 is many things – hilarious, hopeful, occasionally heartbreaking. But it’s also a chance to set your own rules, to bring confidence and good humour to the awkward question of “who pays?”

As for Trevor? He reckons next time he’ll order just one glass. “And if she offers to go halves, I’ll say yes – and maybe we’ll both stay for a second round.”

So who should pay? You tell me. Maybe, in 2025, the answer is whoever wants to nurture the conversation… and is happy to still be in the ring, pinot or no kiss.