For many Sydney hospitality workers, Valentine’s Day – which falls this Friday – is the most punishing and challenging shift of the year. The job can include conjuring extra tables for two from thin air, dealing with razor-high diner expectations, and stepping in as a counsellor following rejected marriage proposals.

How do you respond if ex-lovers turn up to their favourite restaurant with new dates and are seated next to each other? What would the health inspector say about a diamond ring in a dumpling? Is there a statute on compensation when a waiter congratulates a couple before the surprise marriage proposal?

“Brutal, logistically,” is how Justin Newton describes Valentine’s Day service. On Friday, the House Made Hospitality director will oversee a posse of romantic restaurant destinations, including Lana and Tilda restaurants in Sydney’s CBD and Promenade Bondi Beach. “It’s partly because you have so many tables of two, there so many dockets,” Newton says. Then throw in the extra requests of special cakes and hidden rings, which can put a strain on the kitchen and floor staff.

There’s also “the vibe of the room”, which Newton describes as unlike a typical service. The Valentine’s Day crowd – often a mix of established couples and a smattering of first dates – can react differently when a fellow diner goes down on bended knee.

At many restaurants, the set menu is an easy option for a kitchen stretched by Valentine’s requests, or to help claw back the opportunity cost of a table for four occupied by only two guests. But Sam Christie, co-owner of the Apollo and Cho Cho San restaurants in Potts Point, likes to offer diners the choice of a curated Valentine’s Day menu or the authentic a la carte menu.

“The first man got down on one knee, and the whole room erupted in cheers.”

Restaurateur Chris Lucas

Christie says customers’ expectations are “a little bit higher on Valentine’s Day”. “Seating at the bar is good for two, but you can have people asking why they aren’t at a table, and others at a table who want to sit at the bar.”

Newton and Christie remain positive about the spirit of Valentine’s Day dining, and as operators, there is of course the welcome spike in business.

Valentine’s Day service can sometimes morph into dinner and a show, with chefs generally cautious about their role in proceedings when asked to insert engagement rings in food or drinks. Not just because a diamond is the only thing on a pizza more controversial than pineapple – there’s also the apocryphal story of a diner swallowing a ring in a champagne flute.

Restaurant proposals can be particularly fraught. Chef James Kidman, who was executive chef at both Cafe Sydney and QT Sydney, recalls a Valentine’s date running late when he worked at Otto in the noughties.

“He was in contact with her, but she kept stalling him. He finally got a phone call from her saying that she was with another [man] who had just proposed and she had said yes,” Kidman remembers.

“Unbeknownst to her, he [the diner] was also wanting to propose – he had the ring ready to go. The restaurant manager at the time spent half her night consoling him.”

Industry veteran Craig Hemmings has been to a few romantic rodeos. The director of White Horse in Surry Hills explains that it’s the unexpected that can throw a spanner in the Thermomix on Valentine’s Day.

He recalls a woman who once booked a table for two at Opera House fine diner Bennelong – with a stuffed toy penguin as her date. As the restaurant’s general manager at the time, he was used to high-profile guests and unusual requests. But the Valentine and her furry date quickly changed the mood in the restaurant.

“She ordered three courses. For both of them. It certainly added another layer to the atmosphere in the room,” he says.

“Every other table was asking about the woman and her penguin. How does this work? And it just went on. She ate her entree. The penguin did not. She was quite composed.”

Hemmings’ son Max was working as a waiter at Bennelong that night. “I’ll never forget, Max calmly cleared her plate of eaten food, then picked up the uneaten penguin’s dish and asked her politely, ‘Did your friend enjoy his meal?’”

One Valentine’s Day at a Byron Bay restaurant stands out for restaurateur James Lancaster. “A man was having dinner with a woman when his wife turned up at the restaurant,” he recalls. “After a heated exchange, all three left.”

Lancaster, who opened Hazel Kitchen and Bar, in the Sydney suburb of Gymea in November, remembers the reaction in the room. “Customers were turning to each other, saying ‘You wouldn’t do that to me would you?’”

Chin Chin Sydney owner Chris Lucas has a cautionary tale from his Melbourne restaurant Society, where four couples were seated in the same section.

“The first man got down on one knee, and the whole room erupted in cheers. Just as the excitement settled, a second man stood up and said, ‘Well, you’re not going to believe this’, and proposed on the spot,” Lucas recounts.

“A little later, a third gentleman quietly popped the question, keeping things low-key. By the time staff noticed a fourth man nervously fiddling with his pocket, we could hardly believe it. He took his time, but eventually, he dropped to one knee.”

The moral of the story, according to Lucas: if you’re planning something special this Valentine’s Day, let the restaurant staff know.