Sam Milby says he knew that Catriona Gray is “The One” for him because they’re not just lovers, but also best friends.
This was how he described his relationship with Catriona weeks before he announced that they are getting married.
Sam and Catriona made their engagement known on February 16, 2023.
Their post on Instagram showing the official photos from their engagement shoot was one of the rare occasions where they gave a glimpse of how they are as a couple.
But it appears that there’s trouble in paradise.
A year after the engagement, speculation is rife that Sam and Catriona have called it quits.
In this timeline, PEP.ph (Philippine Entertainment Portal) traces how their relationship began, the engagement, and what’s happening now that their road to forever seems to be on pause.
SAM MILBY AND CATRIONA GRAY: THE FIRST SIGHTING
It was in December 2018 when Sam and Catriona were spotted together at a farm in Tanay, Rizal.
The photos that circulated online showed that the two were accompanied by Catriona’s father Ian Gray.
At the time, Catriona was newly crowned as Miss Universe 2018 and was in Manila for a quick Christmas break before she returned to her Miss Universe duties.
That she was seen spending time with Sam made people wonder if they are an item.
While he was not yet handling her showbiz career at the time, Erickson already took on the role as her business manager.
Erickson explained that he owns the farm and it was he who invited Sam and Catriona to come visit his place.
It was also Erickson who told PEP.ph that the two personalities belong to the same church and Bible study group.
It was not yet known at that time that Catriona had broken up with her long-time boyfriend Clint Bondad.
The following month, on February 22, 2019, Catriona revealed in a TV interview that she and Clint are over, but that she intends to remain single during her Miss Universe reign.
WHAT CATRIONA INITIALLY SAID ABOUT SAM
The very first time Catriona was asked if Sam is courting her was when she did a TV interview in December 2019.
All she said was that they go to the same church and that they are “under the same management” which is why they know each other.
Then that was it.
For the whole year of 2019, and even the first few months of 2020, there was no news about her going back to the dating scene.
There were talks that she and Sam had been spotted together sometime in mid-2020, but no photos of them together came out in public.
Then on Sam’s 36th birthday on May 23, 2020, he went public about his relationship with Catriona.
Their status became “Instagram official” when he posted a picture of him and Catriona on his Instagram feed.
The photo showed him giving Catriona a kiss on the forehead.
His sweet caption read: “Worth every second of the wait. Most special birthday yet.”
A day before that, he did a Facebook Live interview where he got a surprise video greeting from Catriona.
When his celebrity friends teased him about it, Sam admitted that he feels “kilig” over Catriona’s unexpected message for him.
Then he admitted that he has “very special feelings” for Catriona.
Sam and Catriona kept a tight lid on their relationship.
But in the few occasions that the press would get to talk to Sam, he would say that he sees Catriona as wife material.
On August 7, 2020, he told entertainment reporters, “I do believe she’s the one, yes.”
Then he also pointed out that because of their nine-year age gap, he wouldn’t rush Catriona into getting married since she’s still establishing her career in showbiz.
The following year, in January 2021, Sam and Catriona reportedly visited his parents in Ohio.
The couple was very low-key about it as they did not post any photos of them together.
But eagle-eyed netizens were able to recognize Sam’s childhood home based on the view of a pond seen in the photos that Catriona posted on her Instagram.
CATRIONA BECOMES MORE OPEN ABOUT RELATIONSHIP WITH SAM
In the following months, Sam and Catriona began to show more glimpses of how they are as a couple.
They spent Valentine’s Day together at a pool resort in Batangas, based on Catriona’s Instagram video.
But instead of posting moments where they’re both in the same frame, she just showed Sam playing around with her pet dog Theo by the poolside.
It was on Sam’s 37th birthday on March 23, 2021 when Catriona finally posted a couple photo on her Instagram feed.
Her sweet caption read: “So sad I can’t be with you today to celebrate (even though you hate birthdays) but I’m so thankful I get to do life with you.”
SAM AND CATRIONA’S DYNAMICS
As their relationship progressed, Sam became more vocal about how well he and Catriona complement each other.
“We just get along,” he told a select group of reporters, including PEP.ph, in an interview dated February 7, 2023.
“Honestly, wala kaming malalaking away. We’re just able to be understanding of each other.”
In a June 2022 interview with PEP.ph, Sam said Catriona never got jealous of any of his leading ladies.
“Just having that understanding na trabaho ko ito, and that the trust is there. I’m thankful that I have someone like that.”
Both of them also said in previous interviews that they have the same love language, which is acts of service to each other.
Then in December 2022, it was Catriona’s turn to bring Sam to her parents’ home in Australia.
They went on picnics by the beach and enjoyed a lot of food trips together.
This was also around the time when rumor came out that Sam and Catriona secretly got married after she was seen wearing a gold ring on her right finger.
On February 7, 2023, Sam clarified that he and Catriona are not yet married.
When pressed about them getting engaged, he evaded the question by saying it wouldn’t be a surprise to Catriona if he announce it first to the media people.
But he did say that he’s set on marrying Catriona whom he considers his “best friend.”
SAM AND CATRIONA’S ENGAGEMENT
It was on February 16, 2023 when Sam finally revealed that he’s engaged to Catriona.
He announced it via Instagram where he posted a picture of him and Catriona holding cups of coffee that bearing the names “Mr. Milby” and “Future Mrs. Milby.”
The shot also highlighted the engagement ring that Sam gave to Catriona.
Sam’s caption read: “I (FINALLY) put a ring on it! [smiley] I love you my forever koala… now my fiancé [heart emoji].”
Catriona’s short but sweet reply: “I love you.”
Sam also posted more photos from their engagement shoot where they posed with his motorbike by the beach.
A motorbike enthusiast, Sam described Catriona as “My ride or die.”
He also noted, “Of all the roads life took me down, I’m grateful that they led me to you.”
Catriona, for her part, also posted photos of their engagement shoot on her Instagram.
She wrote in the caption: “Living in an answered prayer with my best friend. I love you, fiancè (eeeeee).”
That they are taking the next step to their journey to forever is “the best chapter yet” for Catriona.
JUNE-JANUARY 2023
In the succeeding months after their engagement, Sam and Catriona have worked together for a series of concerts with their talent management, Cornerstone Entertainment.
They did a concert with their co-artists, and then they had a separate series of shows for just the two of them.
In November, Catriona even showed her support to Sam during the launch of the Netflix series Replacing Chef Chico, which he co-starred with Alessandra de Rossi and Piolo Pascual.
Sam even threw a surprise birthday party for Catriona, who turned 30 on January 6, 2024.
FEBRUARY 2024
During the first week of February 2024, there was talk in social media that Catriona and Sam have broken up.
Netizens noticed that there were instances when Catriona hasn’t been wearing her engagement ring.
The rumor was later quashed when Sam’s close friend John Prats posted a group photo with his wife together with Sam and Catriona.
But the speculation was fueled again when Ogie Diaz reported about it on February 24.
This Wednesday afternoon, February 28, Sam and Catriona’s talent management Cornerstone Entertainment released an official statement about the issue.
The statement read in part: “While it is true that Sam and Catriona are currently facing some challenges in their relationship, they are actively working on resolving these issues together.”
Will the couple be able to iron things out? Or will their six-year relationship come to an end?
Editor’s Note: This article was first published on February 25, 2023. It was updated on February 28 to include latest information regarding Sam and Catriona’s relationship problem.
