Rob Kardashian does not have the best romantic track record. Click through the gallery for a timeline of his dating history.
1 of 20

In his early days of reality TV stardom, Rob was dating Cheetah Girl
Adrienne Bailon.
Photo credit: Splash News
2 of 20

But despite claiming to be deeply in love with her Rob allegedly cheated on her!
Photo credit: Splash News
3 of 20

Broken hearted, Adrienne removed the large Kardashian tattoo she had emblazoned on her backside, and went on to trash her former lover in the media, fueling a back and forth
feud with his sisters.
Photo credit: Splash News
4 of 20

Unable to win back the woman he once considered the love of his life, Rob moved on to other ladies, including dancer and model Rosa Acosta.
Photo credit: Splash News
5 of 20

The pair had a fling that eventually led to a pregnancy.
Photo credit: Splash News
6 of 20

While the couple had not planned to start a family, Rosa said that Rob was ready to be a dad.
Photo credit: E!
7 of 20

“I took a few pregnancy tests and they came out positive," she told
Star magazine exclusively in 2011.
Photo credit: E!
8 of 20

rob-kardashian-girlfriends-romance-fails14
Then, the unthinkable happened.
Photo credit: Splash News
9 of 20

"The baby didn’t attach," Rosa revealed. "Essentially, I had a miscarriage.” Afterward, their relationship crumbled.
Photo credit: Splash News
10 of 20

Rob also had a brief fling with
Khloe's best friend
Malika Haqq, but a mutual romance was not in the cards for them.
Photo credit: Splash News
11 of 20

Rob then moved on to
Rita Ora, and even tattooed her likeness on his body.
Photo credit: Splash News
12 of 20

But that relationship also went sour when Rita was unfaithful.
Photo credit: Splash News
13 of 20

“She cheated on me with nearly 20 dudes while we were together," Rob tweeted at the time. "I wonder how many she will sleep with now that we apart?"
Photo credit: Splash News
14 of 20

Following that split, Rob began to isolate himself, piling on the pounds, with his sister
Kim saying that his Rita tattoo had become a cabbage patch doll.
Photo credit: Splash News
15 of 20

Photo credit: Splash News
16 of 20

rob-kardashian-girlfriends-romance-fails12
By May, she announced that she was pregnant with their child.
Baby Dream was born in November.
Photo credit: Splash News
17 of 20

18 of 20
19 of 20

Now, Rob is cozying up to
Love & Hip Hop star
Alexis Skyy. She’s infamously feuding with Blac Chyna, so maybe it’s just a ploy to make his ex jealous.
Photo credit: Getty Images
20 of 20

What do you think of Rob’s harried dating history? Sound off in the comments!
Photo credit: MEGA
In his early days of reality TV stardom, Rob was dating Cheetah Girl
Adrienne Bailon.
Photo credit: Splash News
But despite claiming to be deeply in love with her Rob allegedly cheated on her!
Photo credit: Splash News
Broken hearted, Adrienne removed the large Kardashian tattoo she had emblazoned on her backside, and went on to trash her former lover in the media, fueling a back and forth
feud with his sisters.
Photo credit: Splash News
Unable to win back the woman he once considered the love of his life, Rob moved on to other ladies, including dancer and model Rosa Acosta.
Photo credit: Splash News
The pair had a fling that eventually led to a pregnancy.
Photo credit: Splash News
While the couple had not planned to start a family, Rosa said that Rob was ready to be a dad.
“I took a few pregnancy tests and they came out positive," she told
Star magazine exclusively in 2011.
rob-kardashian-girlfriends-romance-fails14
Then, the unthinkable happened.
Photo credit: Splash News
"The baby didn’t attach," Rosa revealed. "Essentially, I had a miscarriage.” Afterward, their relationship crumbled.
Photo credit: Splash News
Rob also had a brief fling with
Khloe's best friend
Malika Haqq, but a mutual romance was not in the cards for them.
Photo credit: Splash News
Rob then moved on to
Rita Ora, and even tattooed her likeness on his body.
Photo credit: Splash News
But that relationship also went sour when Rita was unfaithful.
Photo credit: Splash News
“She cheated on me with nearly 20 dudes while we were together," Rob tweeted at the time. "I wonder how many she will sleep with now that we apart?"
Photo credit: Splash News
Following that split, Rob began to isolate himself, piling on the pounds, with his sister
Kim saying that his Rita tattoo had become a cabbage patch doll.
Photo credit: Splash News
Photo credit: Splash News
rob-kardashian-girlfriends-romance-fails12
By May, she announced that she was pregnant with their child.
Baby Dream was born in November.
Photo credit: Splash News
Now, Rob is cozying up to
Love & Hip Hop star
Alexis Skyy. She’s infamously feuding with Blac Chyna, so maybe it’s just a ploy to make his ex jealous.
Photo credit: Getty Images
What do you think of Rob’s harried dating history? Sound off in the comments!