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Catriona Gray And Sam Milby's *Low-Key* Relationship Timeline

Catriona Gray and Sam Milby's relationship timeline
PHOTO: instagram/jericksanchez via instagram/samuelmilby

Yes, we're still not over longterm couple Catriona Gray and Sam Milby announcing their engagement mere days after Valentine's Day 2023. The two have kept things pretty low-key on social media ever since they admitted to being in a relationship, which means their rare appearances on each others' feeds are that much more exciting.

Before they officially tie the knot, let's take a look back at how Catriona Gray and Sam Milby's love story began via this relationship timeline:

December 2018: Sam congratulates Catriona on winning Miss Universe 2018

Sam was a fan of Catriona even before they dated, and his congratulatory post was one of many that appeared on social media after the beauty queen secured the crown at the Miss Universe 2018 international competition. The actor shared her winning moment on social media and wrote, "Thank you for raising the flag for all Filipinos @catriona_gray !!! You truly deserve the Congrats!!! #missuniverse2018 #catrionagray."


Although she was with then-boyfriend Clint Bondad at the time, Catriona later on revealed that she and Clint were "having some problems even before the pageant."

February 2019: Catriona confirms her breakup with Clint

During an episode of Tonight with Boy Abunda the beauty queen confirmed that she was newly single after she and her long-term boyfriend of six years called it quits. "It was really hard going through the competition with that happening all at the same time," Catriona opened up.

Catriona felt that she and Clint "outgrew each other" and "just didn’t work out." However, she clarified that she still respects him and is grateful for the time they spent together because they supported each other.

TWBA: Catriona's revelations about her break up with Clint

December 2019: Catriona says she's just friends with Sam

In another Tonight With Boy Abunda interview held after her Miss Universe reign ended, Catriona was asked about her love life; specifically about two men particular, who were both linked to her at the time—Sam and Alden Richards.

"I feel like the fans are like shipping, which I guess is a thing that fans do. I’ve never met Alden before," Catriona clarified. "And then Sam naman, we go to the same church, we are under the same management [Erickson Raymundo of Cornerstone Entertainment], so friend naman siya." (Skip to 36:37 for her full answer!)

Catriona Gray | TWBA Uncut Interview

January 2020: Netizens speculate that Sam is the "mystery guy" at Catriona's birthday party

Catriona's friends and talent agency surprised her with a birthday party celebration, and the beauty queen happily shared several polaroids from the event on her Insta. Eagle-eyed fans spotted a photo of a smiling Catriona sat beside a "mystery guy," who many believed to be Sam.

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May 22, 2020: Sam says Catriona is special to him

During a livestream chat with friend and fellow actor John Prats and comedian Pooh, Sam reacted to several pre-recorded birthday greetings from his friends, but the actor was visibly surprised—and could not stop grinning—at Catriona's message (skip to 0:58). "Hey, Sam. Happy, happy birthday! I hope that you have an amazing year ahead. I wish you more birthdays, more happiness. You are loved by so, so many," she said.

John and Pooh then started teasing Sam after they noticed his "kilig face", especially when it became Sam's turn to send a message to Catriona (skip to 4:13, then 5:43). "Nahiya ako...Basta I’m kilig sa message, super kilig sa message. Hindi ko in-expect talaga na mag-message,” he said. "Thank you. And yes, you are very special. Very special."

Btw, in the same livestream Sam admitted that he can be torpe sometimes—"I am a mahiyain na [tao]."


May 23, 2020: Catriona and Sam become Instagram-official

On his 36th birthday, Sam went public with his and Catriona's relationship. Sharing a special polaroid of the two of them where he's seen kissing Catriona's forehead, Sam said it was "Worth every second of the wait. Most special birthday yet."

A polaroid photo of Sam Milby and Catriona Gray on a road

Several of their showbiz friends and colleagues congratulated the couple via comments on Sam's post, but John Prats took it one step further with his *own* cheeky IG upload! "Sa wakas may photo na hindi ikaw ang third wheel!!! Hahaha! Congratulations @samuelmilby and @catriona_gray mahal na mahal ko kayo!!! May God bless you guys! Cheers!!!"

In the photo, John is seen holding Sam’s left hand while Catriona holds his right. John also tagged the couple in the photo, LOL!

August 2020: Sam calls Catriona 'The One'

In a virtual press conference for his ABS-CBN teleserye, Ang Sa Iyo Ay Akin, Sam was asked about the possibility of marriage in the future (around the 1:05:08 mark). Despite their 10-year age difference, the actor explained that he believes Catriona is The One for him. "Siyempre, may difference sa edad naminAko, I'm 36. She's 26, and kaka-start pa lang ng career niya. It’s early, but I do believe she is The One."


Ang Sa Iyo Ay Akin Virtual Media Conference | August 7, 2020

May 23, 2021: Catriona shares her first-ever Instagram post of Sam on his birthday

Since Catriona was in Australia at the time to visit her family, she mentioned in her post that she was "sad" not to be with him on his birthday. "Happy Birthday my love @samuelmilby! 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. ILYSM"

Catriona Gray wants to keep relationship with Sam Milby private.
Catriona's first post of Sam on her Instagram account was for his 37th birthday! Instagram/catriona_gray

The couple are suuuper low-key online and rarely post about each other even on Insta Stories—in fact, Sam's only pic of them together on his IG feed [at this point in time] was when he hard-launched their relationship the year before!

July 2021: Catriona and Sam share the newest addition to their family

On their respective Instagram pages, the couple announced that they adopted a new pupper: A sweet Cavalier King Charles Spaniel named Bailey! "Welcome to the family little boop Bailey Bear!" Catriona said, while Sam kept it simple: "Meet the newest member of the family - Bailey"

Catriona already owns a dog of the same breed, her adorable Theo, who she welcomed on Valentine's Day in 2020. She posted this sweet message on V-Day 2021: "One year of cuddles, kisses, and kulit. one year anniversary with my chookychook Theo, my forever Valentine"


April 2022: Catriona opens up about keeping their relationship private

In a chat with Cosmopolitan Philippines, Catriona discussed why we only see snippets of her relationship with Sam: "I think it’s definitely a conscious decision, an intentional decision to keep our relationship private. Because we don’t want it to be a public consumable."

Part of the couple's motivation for keeping their love life private is to allow them "to have the kind of relationship [they] have now...I don’t think we’re gonna change it going forward," she notes.

May 2022: The couple share the stage together for the first time

Catriona and Sam went on a One Magical Night tour in Canada and made stops at Vancouver, Calgary, and Edmonton, to the delight of Canadian fans. The crowds went crazy over their versions of Bradley Cooper and Lady Gaga's "Shallow" and The Temptations' "My Girl." Catriona had nothing but love for their fans after the successful road show: "As an artist, the joy of performing for a live audience hits different!...Canada, I can't wait to be back!!" 

The couple also made it a point to enjoy the sights despite their busy schedules, and happily played tourist. In one photo, Catriona sweetly shares, "Every view is better with you". She then jokingly apologizes to fans in her next post: "Sorry brb, getting lost in the mountains." Cute!



December 2022: Catriona says she's 'thankful'

Sharing a carousel of photos, Catriona says that *thankful* is "the word of 2022." She also uploaded more photos on January 8, 2023: "A mini photodump from my bday trip in aussie Wine country." Her birthday is on January 6th, FYI.

February 14, 2023: Catriona and Sam spend Valentine's Day together

The couple spent the holiday indoors by themselves, enjoying a peaceful day at home with their dogs: "a quiet little Valentines lunch at home with my favorite person @samuelmilby and the boops". Don't Theo and Bailey look adorable sleeping beside each other?


We love the gorgeous bouquet of red and white roses, and the delicious spread!

February 16, 2023: Catriona and Sam announce their engagement

The Miss Universe 2018 titleholder shared the good news of their engagement on Insta via an adorable couple photo of the two toasting twinning cups of coffee. "Living in an answered prayer with my best friend," Catriona said.

Sam posted the same photo on his profile, captioning his post, "I (FINALLY) put a ring on it! I love you my forever koala... now my fiance."

They also uploaded a few of their engagement photos by photographer Jerick Sanchez. Catriona captioned her post"Our best chapter yet." Meanwhile, Sam called Catriona "My ride or die. ???? Of all the roads life took me down, I'm grateful that they led me to you."


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