Entertainment

Jon Gosselin & Girlfriend Colleen Conrad: A Timeline of Their Love Story

EntertainmentPublished Aug 1, 2019
By Nicole Pomarico
Jon Gosselin and Colleen Conradjongosselin1/Instagram

It's been well over 10 years since we first met Kate Gosselin, Jon Gosselin, and their brood on Jon & Kate Plus 8 on TLC, and so much has changed since then. This former reality star couple has since divorced, resulting in a few serious custody battles that have gotten ugly. But in the end, Jon and Kate were better off without each other. Jon has officially moved on with someone new: His girlfriend, Colleen Conrad, who he's been showing off on Instagram over the past couple of years.

So far, they seem really happy together, and it's been great to see.

Since they first got together sometime in 2014, Jon and Colleen have been hitting all the milestones. Not only have they met each other's kids -- and seem like one big happy family when they're all together --  but they've traveled together, attended events together, and now, even live together.

(This is for real, y'all.)

Of course, there are still plenty of blanks to fill in. Aside from the rare interview here and there and the snippets of their life together that Jon shares on Instagram, he's been pretty private about the lady in his life. But based on what we do know, we can piece together their love story bit by bit. Not only have these two known each other for a long time, but it truly does seem as if this couple isn't going anywhere anytime soon.

Read on for a history of Jon and Colleen's relationship. They've been together for a long time now, and it seems like things are getting serious.

Will we see them walk down the aisle soon? Only time will tell, and for now, it seems they couldn't be happier.

1/20

1980s: Jon Gosselin & Colleen Conrad Meet

During a WeTV panel about love and relationships on reality TV, Jon Gosselin revealed that he and Colleen go way back -- like childhood.

"I've known Colleen my whole life," he said at the time, according to OK! Magazine. "We grew up three blocks from each other. Her sister used to babysit me."

2/20
November 2009: The Last Episode of Jon & Kate Plus 8 Airs-placeholder
November 2009: The Last Episode of Jon & Kate Plus 8 Airs
Amy Sussman/WireImage for Discovery Communications

November 2009: The Last Episode of Jon & Kate Plus 8 Airs

After word got out that Jon and Kate were going their separate ways, the reality show that made them famous came to an end. After that, it became Kate Plus 8, focusing on Kate Gosselin's life as a single mother to eight children and the challenges that came with it. It was a serious bummer for fans, but it was clear that they no longer belonged together.

3/20
December 2009: Jon & Kate's Divorce Is Final-placeholder
December 2009: Jon & Kate's Divorce Is Final
Splash News

December 2009: Jon & Kate's Divorce Is Final

On December 18, 2009, following rumors that Jon had been cheating on Kate with multiple women, their divorce was final. At the time, Kate was awarded full custody of their children. After 10 years of marriage, they were both single again.

4/20

Late 2014: Jon & Colleen Start Dating

Although the official beginning of Jon and Colleen's relationship isn't clear, it seems that they started dating some time at the end of 2014. According to what sources told Entertainment Tonight in July 2015, they'd been together for nine months when they were first spotted out and about. Doing the math, that puts their anniversary sometime in December 2014 -- as long as that source's info is correct.

5/20

April 2015: Their Relationship Becomes Instagram Official

Colleen showed up on Jon's Instagram for the first time in April 2015. Though Jon shared a photo of the two of them together on the beach without much of an explanation, it became clear that this must be the new lady in his life.

6/20

July 2015: Spotted Together for the First Time

That summer, Jon and Colleen were spotted out and about together for the first time, seemingly confirming that this mystery woman from his Instagram is, in fact, his new girlfriend. According to ET's reports at the time, they'd already been dating for months, and Colleen had met Jon's kids. Colleen, a nurse, has two teen children of her own.

7/20

2015: Jon & Colleen Move In Together

The same ET report claims that Jon and Colleen had moved in together shortly after they started dating. The new couple didn't confirm or deny these reports, but it seems safe to assume that things were going pretty well. And since they'd known each other for so long, it's no surprise that they moved quickly in their relationship.

8/20

June 2017: Jon Celebrates Colleen's Graduation

After more than two years together, Jon and Colleen came together to celebrate a major milestone. In June 2017, Jon shared a photo of himself with Colleen on her graduation day. According to his caption, Colleen had graduated from Drexel University with a master's degree in nursing and was officially a nurse practitioner.

9/20
September 2017: Colleen Starts a GoFundMe account for Jon's Custody Battle-placeholder
September 2017: Colleen Starts a GoFundMe account for Jon's Custody Battle
Colleen Conrad/GoFundMe

September 2017: Colleen Starts a GoFundMe account for Jon's Custody Battle

As Jon was embroiled in his custody battle with Kate, Colleen stepped up. She organized a GoFundMe account to help raise money for Jon's legal fees so that he'd be able to fight for his kids. In the end, she raised over $3,000.

"Many people have asked Jon how they could help with his legal fight to win the same rights as other parents: time with his children," Colleen wrote at the time. "This is how. Money raised in this campaign will go to the legal battle ahead as Jon secures his rightful place in the lives of his family."

10/20

October 2018: Jon Shares a New Photo With Colleen

Well into the fall, things seemed to be going well for these two. Jon shared a new photo of Colleen on Instagram as they watched an Eagles game together. Fans who commented on the pic couldn't help but mention how happy they both looked.

11/20

November 2018: Enjoying the Holiday as a Blended Family

In late November 2018, Jon shared a photo of him with his kids, Collin and Hannah, shopping for a Christmas tree with Colleen's kids. Days prior to the snap, Jon filed for custody of Collin, who was still living in the treatment center Kate put him in years prior.

It looked as if they were all getting along pretty well -- especially if they were celebrating the holidays together as a blended family. They all seem super happy!

12/20

December 2018: Jon Wins Custody of Collin

After duking it out with Kate in court, Jon was awarded full custody of Collin, his 14-year-old son, who Kate had placed in a facility because of special needs Jon disputed back in 2016. The win came less than a year after Jon had won custody of Hannah. Looks like that GoFundMe account was put to good use as Collin would seemingly join Jon and Colleen at home.

13/20

Jon Says He Could Propose to Colleen

During the same WEtv panel already mentioned, Jon revealed that marrying Colleen has definitely been something he's thought about. "I've thought about it, yeah -- talked about it," he said at the time.

But when it'll happen?

He stayed quiet on the details.

14/20

Jon & Colleen Take a Trip to California

Just as the holiday season kicked in, Jon and Colleen headed to Los Angeles for a little business and a little pleasure. Relaxing by the pool, sightseeing with friends -- it seemed the couple had a great time. And after more than four years together, it's good to see an updated photo of them, especially because they still looked so happy together.

15/20

January 2019: Ringing in the New Year Together

Jon, Colleen, Hannah, and Collin all spent New Year's Eve together, ringing in 2019 as a family. They all looked like they had a great time, and it was so good to see the kids so happy after the drama they'd been through, especially when it came to their custody case.

Could 2019 be the year Colleen and Jon tie the knot?

16/20

April 2019: Catching a Game Together

Jon and Colleen posted photos from the Phillies game they went to together, and it seemed to be another happy time for the couple. They also went to a sorority mixer for Colleen's daughter, Jordan. With all the family stuff they've been doing together, it seems these two are banking on being together for a long time.

17/20

May 2019: Another Trip to California

In the spring, Jon and Colleen headed out to Santa Monica for a trip. While there, they relaxed together and attended a wedding where Jon was the DJ. They clean up pretty nicely, as we can see in this photo.

18/20

June 2019: Jon Posts a Sweet Message Honoring Colleen

In honor of Colleen's birthday, Jon shared this sweet tribute to his girlfriend in June. Not only was this a gorgeous photo of them both, but his words were so sweet. It seems Jon really appreciates Colleen -- and with a birthday message like this, it makes sense why that they've been together for almost five years.

19/20

July 2019: Jon & Colleen Hit NYC

Yet another trip for this happy couple!

This time, Jon and Colleen went to New York to help her son, Jesse, move. Jon shared this selfie of him and his girlfriend at the Brooklyn Bridge to commemorate their time there.

20/20

Happily Ever After

At the end of July, Jon shared this sweet photo of their names carved into a table inside a heart. Hopefully, this kind of behavior is sanctioned by the restaurant they were at, but it's pretty adorable nonetheless.

We can't wait to see what the future holds for them!

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