For Timothee Chalamet, being introduced to Kylie Jenner's big sisters was always going to be a nerve-wracking moment.
But imagine being flown to a remote castle in the Italian countryside to come face to face with the Kardashians for the first time.
That's exactly what Kylie did when she thought it was time that Timothee got acquainted with her £770 million family - including her tiger mum, the 'momager' Kris Jenner.
MailOnline can reveal that in an attempt to make sure it all went smoothly, Kylie, 27, rented out the entire Reschio Hotel - a converted 10th-century castle with 36 bedrooms nestled in the Italian countryside - and invited the Call Me By Your Name star, 29, as an 'induction' into the family when the pair had been dating for six months.
A well-placed source told MailOnline: 'Kris, Kim, Khloe, Kourtney, Kendall - they'd all met Timothee before but the relationship was very new at that point and they wanted to get to know him properly.
'It wasn't until Timothee went on that holiday with the girls and Kris - and a bunch of Kylie's friends - that he was considered part of the family, it was sort of like an induction holiday.
'And that's really where Kylie and Timothee fell in love, they came back from that holiday a real couple.
'They couldn't keep their hands off each other, kissing by the pool.'
Kylie Jenner pictured enjoying a sunset picnic during her lavish Italian getaway with her family, friends and Timothee
Kylie and Timothee putting on a loved up display at the Golden Globe Awards on Sunday
Timothee pictured on the red carpet at the 82nd Golden Globes on Sunday, January 5
Reschio Hotel is family-run and located on the lush border between Tuscany and Umbria and is built in and around a 10th-century castle with 1,500 hectares of sprawling land studded with paintbrush cypress trees, olive groves and white roads winding down the valley.
After centuries of being passed between Marquisses and noble Italian families, the castle was taken over in 1982 by the Austria-Hungarian family, the Bolzas, who have pledged to restore it to all its former glory after it became abandoned, overgrown and rewilded in the 20th Century.
The 1,000-year-old restored castle welcomed its first guests in Spring 2021, and Ms Jenner rented it out in summer 2023.
With buffet breakfast provided, the rooms are equipped with air conditioning, a free minibar, WiFi and Ortigia bath products.
Each bedroom window looks out over the sprawling estate shrouded by hand-stitched linen curtains and the furniture is made custom made with Italian wood and fabric.
Grand Rooms cost £1,000 a night with stone walls and ancient wooden beams hanging over four poster beds and fresh flowers laid out for guests as they bathe in the exposed bathtubs.
For £1,770 a night, guests can stay in the Grant Suite, a spacious room with lounge area, desk and fireplace stocked with wood and plush velvet armchairs.
Most luxurious of them all, The Tower Suite for £3,298 a night is located in the most ancient part of the castle, built in 900AD, and the two-bedroom suite is spread over five floors and a terrace with panoramic views of the valley and surrounding farm buildings.
During the Italian holiday, Kylie posted a series of glamorous pictures to her Instagram page
Falling in love, the founder of Kylie Cosmetics and Chalamet snuck off for afternoons alone together and enjoyed a picnic of pastries, fruit and Italian wine in a meadow where he bought her a bunch of birthday flowers
Reschio Hotel is family-run and located on the lush border between Tuscany and Umbria and is built in and around a 10th-century castle
The rooftop garden also features an open-air bathtub.
Within the Tower lie the hotel's 'secret spaces' lit by candles and roaring fires which the brochure describes as, 'perfect for an atmospheric dinner for two' or 'post-supper night caps'.
Being the birthday girl, Ms Jenner and her new beau no doubt bagged this area as theirs.
Falling in love, the founder of Kylie Cosmetics and Chalamet snuck off for afternoons alone together and enjoyed a picnic of pastries, fruit and Italian wine in a meadow where he bought her a bunch of birthday flowers.
One of Hollywood's most secret romances, Ms Jenner and Chalamet have kept their now two-year relationship away from the public and the mother-of-two posted pictures of her trip at the time but was careful not to reveal he was with her.
Fans joked that the picturesque Italian holiday meant she was in her 'Timothee Chalamet era', due to his role in the dreamy romance film Call Me By Your Name, but none knew he was, in fact, there.
But the Mail can confirm the Complete Unknown star was present and joining in on all the activities including pasta-making, long sunset drinking sessions by the pool and wild swimming in Lake Trasimeno.
Ms Jenner's older sister, Kendall, 29, a keen equestrian, was no doubt overjoyed by the purebred Spanish stallions waiting in the stables with guests encouraged to explore the grounds on horseback.
Kylie pictured strolling around Italy during the romantic trip wearing jeans a white flowing top
This scenic shot showed the clear blue swimming pool in the backyard of the property that Jenner and Timothee was staying at, with several green tress in the background
Khloe Kardashian also posted snaps from the vacation in which she is seen wearing a navy blue dress and nude flip flops
Also strongly recommended is a pair of binoculars for scanning the vast countryside for wild boars or falcons.
Elsewhere in the hotel is a tennis court and library which is also home to a cat who prowls the bookshelves and is so unique in its home and habits that it's been ruled by authorities as a national treasure.
Hotel staff wait at every corner to cater for the family's 'every whim' with a babysitting service on hand for £20 an hour - Ms Jenner shares six-year-old daughter, Stormi, and two-year-old son, Aire, with her former partner and rapper, Travis Scott.
Settled in a landscape of fragrant gardens and mature cypress trees, the large heated oval pool gives the illusion of wild swimming in the surrounding ancient vineyards but has a pool bar.
The cellars once meant for wine have been converted into a spa entered by ancient stone steps leading into a warren of soothing spaces, including two treatment rooms, a sauna and a hammam. Among the caves is also a plunge pool of almost celestial calm lit, as it is, by beams of light from windows high above.
A cookery school is also located in the hotel for guests to be led on foraging walks in the grounds which guests pick and choose what they want and then make into Italian meals - Ms Jenner enjoyed an afternoon doing so.
Khloe posted a sweet album that showed her and True frolicking through a field of sunflowers
Kylie seen arriving in Perugia with her sister Khloe Kardashian and niece True, six, less than a week after celebrating her 26th birthday
Khloe pictured wearing a crop top and tracksuit bottoms as she arrived in Italy with her daughter True and Kylie
In another post, the mother-of-two donned a pinup-inspired outfit during a nighttime outing in Italy
Kylie flaunted her curves in Italy while wearing a pastel yellow bikini top as well as matching thong bikini bottoms in a snap shared to her Instagram
Kylie Jenner showed off her cooking skills during a pasta making session with Khloe and Kris
The makeup mogul was spotted shaping pasta dough with Kris and Khloe in a large kitchen with a half-full bottle of red wine open
Kim Kardashian showed off her incredible figure as she posed up a storm in skimpy swimwear while enjoying a swim in Italy
Kim was snapped riding a bicycle in her bikini around the pool during the steamy photoshoot
At the end of a long day of partying, long dinners were enjoyed in the umbrella pine-shaded courtyards with local delicacies served such as fresh pasta and wines.
Just a month after their successful holiday in the Italian countryside, the beauty mogul and the Dune star decided to publically confirm their relationship after they were spotted kissing at the US Open in September.
They have since been pictured only a handful of times together with fans bewildered by the relationship between a willowy 'arty' French-American actor and a Los Angeles-based influencer known for her role on the reality show, Keeping Up With the Kardashians.
But the couple once again defied expectations and proved they were more in love than ever when they posed at the Golden Globes together, their lips locked in a kiss.