Catriona Gray and Sam Milby’s relationship: A complete timeline
Sam Milby and Catriona Gray. Image: Instagram/@catriona_gray
Wedding bells will soon be ringing for Catriona Gray and Sam Milby as the celebrity couple have announced that they are finally engaged after years of dating.
The couple, who have always been low-key about their relationship, made their engagement public over a month after speculations that Milby had already popped the question made rounds on social media. For their fans, there may have been no better way of marking the month of love other than with a celebration for the couple’s milestone.
To join in the celebration, let’s look back at Gray and Milby’s romance—from the beginning to the moments leading to their engagement announcement.
December 2018: Milby congratulates Gray for winning Miss Universe 2018 pageant
The actor-singer was one of the celebrities who expressed pride after Gray won the Miss Universe 2018 title. He posted a photo of Gray from the pageant, thanking her for “raising the flag for all the Filipinos.”
Meanwhile, Gray was still with her longtime boyfriend Clint Bondad at the time, but the beauty queen later revealed that she and Bondad already had problems even before the pageant, and that they were not “on speaking terms so much.”
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January 2019: Gray and Milby were first spotted in Rizal together
Gray and Milby first sparked dating rumors after photos of them along with the beauty queen’s father went viral on social media. Cornerstone Entertainment manager Erickson Raymundo, who handles the artists, then clarified at the time that he had invited Gray and Milby to visit his farm in Rizal, and that the pair’s meeting was “coincidental.”
Raymundo added that Gray and Milby were attending the same church and Bible study group, and that the public should not speculate romantic connections between the two.
February 2019: Gray confirms breakup with longtime boyfriend Clint Bondad
Gray confirmed her split with Bondad, saying they “outgrew” each other during their six years as a couple. Gray also stated that having been in a relationship since she was 18, she never had the chance to “establish [her] own identity as [her] own person.”
December 2019: Gray says she’s friends with Milby
Gray was asked about her relationship with the two men being linked to her at the time: Alden Richards and Milby. Gray clarified that she had yet to meet Richards at the time, and that fans were just “shipping” them. Meanwhile, she called Milby her “friend” and reiterated that they were under the same management and attending the same church.
January 2020: Milby speculated to be the ‘mystery guy’ at Gray’s birthday party
The beauty queen was treated to a birthday surprise by her talent agency and she posted Polaroids from the event on her Instagram page. Eagle-eyed fans then noticed a photo where Gray was all smiles while beside a “mystery guy” who was speculated by netizens to be Milby.
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May 2020: Milby confirms relationship with Gray on his 36th birthday
The actor-singer marked his 36th birthday by making public his relationship with the beauty queen. Milby showed a photo of them where he was kissing Gray’s forehead, captioning his post with “Worth every second of the wait. Most special birthday yet.”
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July 2020: Milby vows to protect Gray amid ‘false accusations, baseless claims’
Milby came to Gray’s defense after her ex-boyfriend Bondad posted a series of cryptic tweets including a “Dating App≠Church” post, which netizens had connected to Gray’s January 2020 statement that she and Milby were just good friends who went to the same church.
Milby stressed that Gray was “one of the kindest souls” he had ever known, and that their decision to keep their relationship private “does not mean that there is truth to any of [the] false stories and fake news that people are creating to fill in the bills.”
At the time, malicious stories against the beauty queen also circulated online, prompting Gray to file a complaint before the National Bureau of Investigation (NBI) against the person who allegedly leaked a “digitally altered” photo of her.
August 2020: Milby declares Gray is ‘the one’
Milby revealed that although he and Gray were taking things slow given their 10-year age gap, the actor-singer already saw Gray as “the one” for him. He added that Gray was just starting her career and that they had yet to touch on the topic of settling down.
May 2022: Gray and Milby share stage for the first time
Gray and Milby went on a Canada tour which marked the first time they performed on a stage together. The couple sent their fans gushing with their rendition of Bradley Cooper and Lady Gaga’s “Shallow” and The Temptations’ “My Girl.”
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November 2022: Milby admits excitement over settling down with Gray
Milby was asked about his plans of settling down and confessed that he was “excited” to settle down and have children. He then admitted that he and Gray had been having talks about settling down, but he noted that he did not want to speak for Gray.
Milby said he had been looking forward to getting engaged to Gray, and that the public would just be surprised when they announced it.
December 2022: Gray and Milby spark engagement speculations
Gray showed herself on a picnic with the actor-singer in Australia with the caption “Today made me the happiest.” This led fans to speculate that Milby might have proposed to the beauty queen during their cozy moment.
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The couple laughed off and denied the said rumors as well as the apparent marriage speculations. However, the pair had noticeably been hinting about the next phase of their relationship, saying they “have been together long enough” and that they had been talking about their wedding.
February 2023: Gray and Milby are set to tie the knot
Gray and Milby announced their engagement by showing a photo of them close to each other while holding cups with the words “Future Mrs. Milby” and “Mr. Milby.” Gray’s diamond ring was also shown in the photo.
The couple declared their love to each other, with the beauty queen saying she is now “living in an answered prayer with [her] best friend.” /ra
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