‘Please, for heaven’s sake, not a pear-shaped diamond with a gold band’: Proposal etiquette for the modern man

The best thing about a proposal, I am led to believe, is not the moment itself, but the days that follow when the new reality begins to sink in. ‘It’s bliss,’ says Sasha Reviakin, a social entrepreneur and policy researcher who became affianced to Lady Henrietta Stanley last June, after proposing in the botanical gardens of Cordobà. (The two had been dating for a year.) ‘We told everyone we knew we had to tell — family and closest friends — on the day it happened, blitzing through calls and Facetimes before switching off our phones and disappearing for two days.’ Sasha had booked himself and Hetty into a suite at Finca La Donaira, an edenic retreat up in the hills surrounding Montecorto in Andalusia. ‘That was the best bit, I think,’ he tells me over the phone. ‘That liminal space after the proposal, but before returning to London where we could relish being engaged à deux without the fanfare that we knew would greet us back home.’

Sasha is among several friends who have proposed to their partners in the past year. They are modern, plucky and enterprising young men who have taken the plunge at a tender(ish) age. Oscar Lewisohn, the youngest, is 26; Sasha, the oldest, is 29. All five are wildly different. Oscar is a music producer and more likely to bet on dogs than on horses. My friend George Chichester, by contrast, has only ever worn a T-shirt on occasions where he has been gifted one.

This has, naturally, led to them elaborating quite different proposals for their sweethearts. Yet within these differences have emerged some commonalities, namely around choice of location, a sense of ceremony and the odd element of surprise. (Getting down on one knee, according to each man, remains important.) Although a greater range of relationship-types has emerged since our parents took the plunge — civil partnerships, gay marriage, polyamory — it seems as though proposal etiquette has not evolved nearly as fast. Which is, in itself, revealing.

My friends’ engagements have come at an interesting time: Britain is currently experiencing a marriage and relationship crisis, with more people single, unmarried or living alone now than at any other moment in the country’s history. Yet they are also an indication that the tide may be turning (Gen Z couples, I wrote last July, are more likely to get married younger than their Millennial counterparts). If a possible reason for this phenomenon is a desire among the youth for more order and heritage, it seems as though contemporary engagement etiquette is also a sucker for tradition.

It is in such a spirit that our current white knights — George, Sasha, Oscar and more besides — have shared their wisdom with me, so that I may pass this onto you in my newfound role as proposal etiquette medium/expert. With the following bylaws, you’d be hard-pressed to find anyone who wouldn’t say yes.

Location, location, location

Some love nothing more than the idea of a domestic proposal: at home, on the sofa, reading the papers or going about the day. My peers and their partners took a broadly different view. Since a proposal is not something you do every day, they thought, it really ought to take place somewhere special. This doesn’t have to be extravagant: Oscar proposed to his girlfriend in Central Park while on holiday in New York, and George proposed to his girlfriend on a Sunday afternoon on Hampstead Heath. Both endeavoured to find a quiet spot with not many people around — which we’ll come to, shortly.

Some will, of course, push the boat out to mark the occasion. Gaspard de Vulpian, our knight in shining armour on the other side of The Channel, proposed to his girlfriend — the chef Sveva Guedroitz — in the middle of the Kenyan savannah, in May 2025. A few months later, Ed McGovern proposed to his girlfriend on the terrace of their villa at the One&Only in Greece. ‘As a theatre producer,’ says Ed, ‘I had planned every umpteenth detail of the evening and liaised with the hotel manager for two months before we flew out, to make sure all the timings would be perfect.’

Many will romanticise the idea of a proposal in the exact spot where they and their partner first met. This can be limiting, however, since couples often end up meeting at a dinner party, in a bar or, increasingly, online. Crucially, you want to avoid any location where it’s easy to be disturbed or distracted. The biggest faux-pas when it comes to proposing, said all the boys I spoke to, is to do so somewhere public. A proposal is an inherently private ritual (Sasha, George and Oscar all managed to find quiet areas in the public parks where each of them knelt), and an agreement reached between two hearts and minds, away from prying eyes or the expectations of others. That includes hidden photographers, whether or not the practice has been endorsed by Taylor Swift.

A mutual agreement

Hollywood has long taught us that a proposal should sweep a woman off her feet. This is nonsense. A proposal should be the confirmation of a decision you have already taken jointly to spend the rest of your lives together. ‘Marriage,’ says Gaspard, ‘has to be something you discuss together for quite some time before you actually get down on one knee and say the four magic words.’

This doesn’t mean the proposal cannot have an element of surprise. Ed says he’d actively tried to lay his girlfriend off the scent, while Oscar flew both his and his new fiancée’s families to New York so they could wait at the hotel for a surprise right after the engagement. (A tough call to make if you’re not certain of being told ‘yes’.) Yet the emphasis here should be on the word ‘element’.

It’s also fun to keep yourself guessing: does your future bride, or groom, know whether or not you’re about to propose? Oscar reckons his fiancée had no idea; to her, their stroll was literally just another walk in the park. George is more sceptical. ‘I think Hannah sussed it out,’ he tells me. ‘We both had incredibly busy summers with work and I remember insisting that she keep that particular Sunday free… She must have known I had something special planned.’ ‘Don’t ever assume the bride doesn’t know what you’re doing, or where your head is at,’ adds Sasha. ‘After I proposed to Hetty, she revealed that she’d already asked her family to put Knowsley Hall [their family seat] on hold for a date in July, because she suspected I might ask for her hand and she wanted to lock down the best weekend for the festivities.’

Put a ring on it

Choosing a ring is often the most nerve-wracking part of a proposal. (‘There is no shame in asking their best female friend for assistance,’ says a source who wishes to remain anonymous.) Given the price of gold has shot back up after a brief respite two weeks ago, silver is proving a popular alternative — although today, the most typical scenario is to use a family heirloom. If said heirloom is a ring, it can either serve as the definitive, forever ring, or used as a temporary placeholder while the future bride searches for a more bespoke — and permanent — model. Yet it doesn’t have to be a ring: it can also be a brooch, which the right jeweller can nimbly pick apart and reassemble as an anneau. Eleanor Stephenson, who became engaged to William Graham-Campbell last September, recommends Eliza Walter, founder of Lylie Jewellery, and says she and William will keep his grandmother’s ring as a placeholder for when their own children, and later grandchildren, take the plunge.

Sasha very nearly proposed ‘in the car park at the airport in Spain’, because ‘I was so stressed about travelling with the ring,’ he says — with good reason. My friend Hughie Shepherd-Cross proposed to his fiancée, Olivia, on holiday in Italy last September, although his plan was temporarily thwarted when British Airways left his luggage on the ground at Gatwick. (He had, naively, put the ringbox in a cabin bag on the basis that Olivia would never find it there.) His panic upon finding out about the hiccup from airport staff almost gave the game away (‘Hughie doesn’t really stress,’ Olivia laughs), although fortunately, the luggage was repatriated to its rightful owner and the couple were engaged — ring and all — by the time they boarded the flight home.

Whatever ring you choose, just keep it close to your heart (read: in the inner pocket of your jacket), and be careful when taking said jacket off or putting it on. And please, for heaven’s sake, not a pear-shaped diamond with a gold band.

A proposal is not a spectacle, but there is an element of ceremony

‘Getting down on one knee is important, I think,’ says Ed, recounting his own proposal for me step-by-step (or, indeed, limb-by-limb). Although one should obviously avoid making their proposal a spectacle, that doesn’t mean we should ignore the element of ceremony inherent in asking for one’s hand. In other words, getting down on one knee is the done thing for a reason — which you might want to bear in mind before you sit down on a bench and decide to kneel from there. It sounds impractical, and it is. ‘I sort of forgot that I was 6ft 7,’ says George, who duly ‘slumped’ from the bench on Hampstead Heath where he’d found himself wanting to propose, onto the ground in a manner reminiscent of Flat Stanley on acid. ‘That bit was complicated.’

One usually (advisably) prefaces the big question with a preamble (‘I’ve been thinking about this for some time’, ‘I love you and I want to spend the rest of my life with you’, etc.). It’s easy for this to feel soppy or dramatic — and good, therefore, to inject a little fun into it. Gaspard, who’d created an elaborate proposal while he and Sveva were camping in the bush (‘the nearest rangers were several miles away: we had only Nature as our witness’), did this beautifully. ‘I knew we were both going to get very emotional,’ he says, ‘and I didn’t want those emotions to cloud what I was going to say… I’d written a little speech which I’d rehearsed at length — it’s worth doing if you don’t want to risk feeling overwhelmed and blurting out something trite.’

He weaved in some levity. ‘I’d built my speech on the idea of a life together: those moments that you look back on later in life, from important events like your wedding to stuff that’s completely innocuous, like when your kid brings home a bad grade in maths… You never know what’s going to mark you, right? Anyway, I’d prepared a slideshow of pages to accompany my proposal and got an AI server to mock up what we might look like as grandparents based on a photo of us now, which brought some much-needed relief at that point in the proposal.’

Careful when asking for a blessing

Also part of the preamble, for some, is asking the future in-laws for a blessing. In yet further evidence that tradition is back in style, nearly all the men interviewed for this feature let the bride’s parents know that they were going to pop the question. (‘Took you long enough,’ George’s future father-in-law told him.) It’s important, however, to do this without ambiguity. ‘I thought I’d done it perfectly,’ says Sasha. ‘I’d taken Hetty’s father out for a beautiful lunch and a bottle of wine, and got quite emotional when I explained that I planned to live the rest of my life with her. I thought I’d been very clear — until his thank-you letter, where he said he considered himself “on notice for a formal question,” which meant I had to ask again over the phone, more explicitly, a second time. Clearly, my sentimental Russian side won out.’

Enjoy the limbo

So, what happens now? After you propose, Gaspard advises, ‘it doesn’t feel so much as if a weight has been lifted off your shoulders and more like one kind of adrenaline is being replaced with another. A bit like when you’re a kid and you get a new toy for Christmas, and you spend the next week or two playing with it relentlessly.’ It joins what Sasha was saying at the start: that blissful, first honeymoon period after the proposal where it feels as though you’re floating on a cloud. You’ll want to extend that for as long as you possibly can (for these, really, are the moments you’ll remember the proposal by). ‘It’s the best thing about it all,’ says Ed, ‘telling random strangers around you on holiday that you’ve just gotten engaged: the waiter, the guy selling olives on the market stall in the local town… It’s great to keep away from the world for a little while and stave off your return to real life.’