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2009-2013: Jesse Metcalfe and Cara Santana begin dating
Peter Larsen/WireImage

After getting together in 2009, Santana and Metcalfe were rarely seen in public together until they began to post about their relationship on Instagram four years later.
02of 17March 9, 2013: Cara Santana spends time with Jesse Metcalfe and his mother in N.Y.C.Jesse Metcalfe/InstagramTheactress and fashion bloggergrew close to theJohn Tucker Must Diestar’s family throughout their 10-plus-year relationship. She’s seen here withMetcalfe and his mom, Nancy,in N.Y.C. in March 2013.In the caption, Metcalfe referred to Santana and his mother as his “2 favorite ladies.”
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March 9, 2013: Cara Santana spends time with Jesse Metcalfe and his mother in N.Y.C.
Jesse Metcalfe/Instagram

Theactress and fashion bloggergrew close to theJohn Tucker Must Diestar’s family throughout their 10-plus-year relationship. She’s seen here withMetcalfe and his mom, Nancy,in N.Y.C. in March 2013.
In the caption, Metcalfe referred to Santana and his mother as his “2 favorite ladies.”
03of 172014: Jesse Metcalfe and Cara Santana adopt a rescue dogJesse Metcalfe/InstagramBy 2014, the couple had welcomed their rescue dog Dexter and posted a sweetfamily phototo share with the world.The following year, Metcalfe and Santana brought Dexter and a new pup, Shepherd, totake a photo with Santa Clausat the Beverly Center in Beverly Hills in November 2015.
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2014: Jesse Metcalfe and Cara Santana adopt a rescue dog

By 2014, the couple had welcomed their rescue dog Dexter and posted a sweetfamily phototo share with the world.
The following year, Metcalfe and Santana brought Dexter and a new pup, Shepherd, totake a photo with Santa Clausat the Beverly Center in Beverly Hills in November 2015.
04of 17April 2014: Jesse Metcalfe and Cara Santana attend a Coachella pool partyJesse Metcalfe/InstagramThe fun-loving pair documented the many trips, activities and vacations they’ve gone on together on Instagram.Metcalfe and Santana lounged in a pool at Coachella in 2014. That year Santana documented her party-hopping Coachella experience forE! Online.
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April 2014: Jesse Metcalfe and Cara Santana attend a Coachella pool party

The fun-loving pair documented the many trips, activities and vacations they’ve gone on together on Instagram.
Metcalfe and Santana lounged in a pool at Coachella in 2014. That year Santana documented her party-hopping Coachella experience forE! Online.
05of 17May 2014: Jesse Metcalfe and Cara Santana give back to UNICEFJesse Metcalfe/InstagramBoth Metcalfe and Satnana have also posted about theircharity work with UNICEF, like when they visited thePandamatenga Village Clinicin Botswana andmet with the children of Mabutsane Villageas part of the organization’s Early Childhood Development Project.The couple shared their experiences inan interview with UNICEF.
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May 2014: Jesse Metcalfe and Cara Santana give back to UNICEF

Both Metcalfe and Satnana have also posted about theircharity work with UNICEF, like when they visited thePandamatenga Village Clinicin Botswana andmet with the children of Mabutsane Villageas part of the organization’s Early Childhood Development Project.
The couple shared their experiences inan interview with UNICEF.
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07of 17July 4, 2016: Jesse Metcalfe and Cara Santana celebrate the holiday together in MalibuJesse Metcalfe/InstagramMetcalfe and Santana have also spent several July 4ths together, including in 2016.“The 4th of is for lovers!!!❤️💙,” Metcalfecaptionedthis romantic shot of the two at Little Dume Beach in Malibu, California.
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July 4, 2016: Jesse Metcalfe and Cara Santana celebrate the holiday together in Malibu

Metcalfe and Santana have also spent several July 4ths together, including in 2016.
“The 4th of is for lovers!!!❤️💙,” Metcalfecaptionedthis romantic shot of the two at Little Dume Beach in Malibu, California.
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August 2016: Jesse Metcalfe and Cara Santana get engaged

After many years of dating,Santana and Metcalfe got engagedin August 2016. The news came shortly after the fashion blogger celebrated her 32nd birthday on Aug. 15.
“Missing This View And Last Weekend Already // But So Excited For The Future Year,” shewroteon Instagram the day after her birthday.
09of 17September 22, 2016: Cara Santana discusses her wedding plans with Jesse MetcalfeDonato Sardella/GettyA month after their engagement news, Santana told PEOPLE that although they were in no rush to start planning, the two would begetting married in September 2018.“I"m going to start planning this time next year,” she said in September 2016 at the WEI Beauty Detoxifying Skincare Line luncheon in Hollywood.“Small, intimate, 80 people, Martha’s Vineyard - call it a day,” Santana continued.She also admitted that the two factors she would be “very particular” about would be food and accommodations.“I want to make sure my guests enjoy,” she added, “But anything else I’m like whatever.“However, Santana wasn’t going to be the only one in charge of her big day. She told PEOPLE that her then-groom-to-be would beinvolved with the planning.“Every guy is like, ‘No, No,’ but Jesse has more opinions than whatever has the most opinions, so he’ll definitely be inputting,” said Santana, adding Metcalfe “has great taste, so I’m happy.“And if Metcalfe’s ring choice was any indication, his wedding choices likely didn’t disappoint.“He did a beautiful job,” Santana said of her stunning engagement ring.After being asked if anything had changed since Metcalfe put a ring on it, the actress said, “I think there’s a sense of calm. There’s a sense of unspoken security that when you’re not engaged maybe there’s like an underlying uncertainty.“She continued: “Now that we’re engaged I feel this total sense of calmness. Like we’ll get to the wedding. We’ve got the rest of our lives.”
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September 22, 2016: Cara Santana discusses her wedding plans with Jesse Metcalfe
Donato Sardella/Getty

A month after their engagement news, Santana told PEOPLE that although they were in no rush to start planning, the two would begetting married in September 2018.
“I"m going to start planning this time next year,” she said in September 2016 at the WEI Beauty Detoxifying Skincare Line luncheon in Hollywood.
“Small, intimate, 80 people, Martha’s Vineyard - call it a day,” Santana continued.
She also admitted that the two factors she would be “very particular” about would be food and accommodations.
“I want to make sure my guests enjoy,” she added, “But anything else I’m like whatever.”
However, Santana wasn’t going to be the only one in charge of her big day. She told PEOPLE that her then-groom-to-be would beinvolved with the planning.
“Every guy is like, ‘No, No,’ but Jesse has more opinions than whatever has the most opinions, so he’ll definitely be inputting,” said Santana, adding Metcalfe “has great taste, so I’m happy.”
And if Metcalfe’s ring choice was any indication, his wedding choices likely didn’t disappoint.
“He did a beautiful job,” Santana said of her stunning engagement ring.
After being asked if anything had changed since Metcalfe put a ring on it, the actress said, “I think there’s a sense of calm. There’s a sense of unspoken security that when you’re not engaged maybe there’s like an underlying uncertainty.”
She continued: “Now that we’re engaged I feel this total sense of calmness. Like we’ll get to the wedding. We’ve got the rest of our lives.”
10of 17February 2017: Jesse Metcalfe and Cara Santana show off their homeThings seemed to have been going smoothly as Metcalfe and Santana were featured inArchitectural Digestin February 2017, showing off their gorgeous West Hollywood home.“She really shines in the pillow department!” Metcalfe told the outlet. Their living room arrangement was featured in the spread, showing several neutral-tone pillows laying on top of a large comfy couch.“It gets amazing light and has great flow,” Metcalfe continued. “It’s also where I play the majority of my music,” he added, referencing their grand piano - which can be seen next to their floor-to-ceiling living room windows.
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February 2017: Jesse Metcalfe and Cara Santana show off their home
Things seemed to have been going smoothly as Metcalfe and Santana were featured inArchitectural Digestin February 2017, showing off their gorgeous West Hollywood home.
“She really shines in the pillow department!” Metcalfe told the outlet. Their living room arrangement was featured in the spread, showing several neutral-tone pillows laying on top of a large comfy couch.
“It gets amazing light and has great flow,” Metcalfe continued. “It’s also where I play the majority of my music,” he added, referencing their grand piano - which can be seen next to their floor-to-ceiling living room windows.
11of 17December 9, 2018: Jesse Metcalfe celebrates his 40th birthday with Cara SantanaJesse Metcalfe/InstagramThe couple’s said wedding date of September 2018 came and went, but things seemed to remain okay between the two. Metcalfe posted a photo with Santana holding giant balloons, while celebrating the actor’s 40th birthday.“Can you believe this sh*t?! 40! Time flies when you’re havin' fun,” hewrote. “Thank you so much, babe, for making the big 4 0 a whole lot less painful. You sure know how to make a guy feel special. Love you!”
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December 9, 2018: Jesse Metcalfe celebrates his 40th birthday with Cara Santana

The couple’s said wedding date of September 2018 came and went, but things seemed to remain okay between the two. Metcalfe posted a photo with Santana holding giant balloons, while celebrating the actor’s 40th birthday.
“Can you believe this sh*t?! 40! Time flies when you’re havin' fun,” hewrote. “Thank you so much, babe, for making the big 4 0 a whole lot less painful. You sure know how to make a guy feel special. Love you!”
12of 17December 25, 2019: Jesse Metcalfe and Cara Santana spend Christmas in BelgiumOver the holidays, the couple traveled to Europe, including London and Belgium, where they celebrated Christmas together. In an Instagram post shared Dec. 26, 2019, Santana explained that she and her fiancé decided to “give each other an experience” instead of exchanging tangible presents for Christmas.She explained that “the idea was tocreate memories, see a new culture and focus on the most important but often most intangible gift that life has to offer: time well spent.““He picked the place, I handled the travel and we invited my family. And man, were we NOT disappointed!” said Santana. “We couldn’t have thought of a better way to spend the winter holiday ❄️ together in #Brugge. ⭐️.”
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December 25, 2019: Jesse Metcalfe and Cara Santana spend Christmas in Belgium
Over the holidays, the couple traveled to Europe, including London and Belgium, where they celebrated Christmas together. In an Instagram post shared Dec. 26, 2019, Santana explained that she and her fiancé decided to “give each other an experience” instead of exchanging tangible presents for Christmas.
She explained that “the idea was tocreate memories, see a new culture and focus on the most important but often most intangible gift that life has to offer: time well spent.”
“He picked the place, I handled the travel and we invited my family. And man, were we NOT disappointed!” said Santana. “We couldn’t have thought of a better way to spend the winter holiday ❄️ together in #Brugge. ⭐️.”
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January 22, 2020: Jesse Metcalfe and Cara Santana split up

Two years later,the two splitafter Metcalfe was seen getting cozy with a woman at a bar in Sherman Oaks, California.
A source told PEOPLE that the actor and the actress-fashion blogger went their separate ways three weeks earlier. However, another source close to Santana told PEOPLE that the pair didn’t break up until Jan. 22, 2020, after Santana saw the photos.
“She was wearing her ring yesterday,” the source close to Santana said. “She had no idea things weren’t fine until she saw the photos online today. I promise they never broke up until today.”
A rep for Santana told PEOPLE, “Cara is not going to comment and asks that everyone please respect her privacy at this time.”
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January 22, 2020: Cara Santana “had no idea things weren’t fine” with Jesse Metcalfe
Fernanda Calfat/Getty

The sad news came just one week after Metcalfe spoke to the Hallmark Channel’sBubbly Seshpodcastabout his fiancée.
“Probably when I proposed was my most romantic moment,” he said, explaining that while wedding planning was at a bit of a standstill, he and Santana were enjoying their time as an engaged couple.
“We really kind of have it on hold right now,” Metcalfe said when asked about wedding plans. “We were doing it not long after we got engaged, and then it kind of like just lost momentum. But I’m sure it will pick up momentum again. We’ve both just been very busy with work.”
15of 17January 22, 2020: Cara Santana’s friend Olivia Culpo defends her after split from Jesse MetcalfeAri Perilstein/Getty ImagesLongtime friend Olivia Culpo came to Santana’s defense after the split. Sheshared two postson herInstagram Storiesthat seemingly accused Metcalfe of cheating.“Don’t cheat… Nobody likes a cheater,” one post read, along with a photo ofRachel McAdamsas Regina George inMean Girls.The second post featured a still of Macaulay Culkin holding a BB gun as Kevin McCallister inHome Alone. “When somebody upsets my best friend,” Culpo wrote, tagging Santana.
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January 22, 2020: Cara Santana’s friend Olivia Culpo defends her after split from Jesse Metcalfe
Ari Perilstein/Getty Images

Longtime friend Olivia Culpo came to Santana’s defense after the split. Sheshared two postson herInstagram Storiesthat seemingly accused Metcalfe of cheating.
“Don’t cheat… Nobody likes a cheater,” one post read, along with a photo ofRachel McAdamsas Regina George inMean Girls.
The second post featured a still of Macaulay Culkin holding a BB gun as Kevin McCallister inHome Alone. “When somebody upsets my best friend,” Culpo wrote, tagging Santana.
16of 17April 2020: Jesse Metcalfe and Cara Santana spotted together after breakupThree months after breaking up, Metcalfe and Santana werespotted running errands togetherin L.A. over the weekend of April 18-19, 2020.The couple were alsophotographed together at a gas stationearlier that month.
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April 2020: Jesse Metcalfe and Cara Santana spotted together after breakup
Three months after breaking up, Metcalfe and Santana werespotted running errands togetherin L.A. over the weekend of April 18-19, 2020.
The couple were alsophotographed together at a gas stationearlier that month.
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April 22, 2020: Jesse Metcalfe and Cara Santana are not back together
The source added that Metcalfe and Santana were on civil terms and living on same property because of the COVID-19 pandemic.
source: people.com