The Hills: New Beginnings star, 36, miscarried for the second time eight weeks into her most recent pregnancy.
Whitney Port
Whitney Port
| Credit: Frazer Harrison/BFC/Getty Images

The last two years have been quite the roller coaster for Whitney Port, and the ride is not over just yet.

The Hills: New Beginnings star, 36, visited Chicago this week to assist her sister, Jade, as she gave birth to her baby boy, Tate. Coincidentally, it is the same week Port was expected to give birth to her second child.

Unfortunately, Port miscarried after eight weeks of pregnancy. It was her second miscarriage in the last two years.

Port reflected on the unfortunate situation on Instagram following her nephew's birth.

"Crazy to think I would have had a newborn within this week too," she wrote atop a photo of her cradling her sister's newborn. "... Sad to really think about it, but I just wanted to say it just to get it out of my head and send everyone who is dealing with some kind of fertility issue a virtual hug."

Whitney Port

In July 2019, Port miscarried for the first time. She and her husband, Tim Rosenman, were looking forward to expanding their family of three and bringing a sibling into the world for their son, Sonny Sanford, who turns 4 next month.

Port has long used her platform to encourage others to have "difficult conversations" about their personal experiences with miscarriage. "I welcome anyone to share their stories or feelings," she said two years ago on her With Whit podcast.

The reality television star has not shied away from discussing her own experiences either.

At the time, Port said the experience led to "guilt" after her shock and sadness eventually morphed into relief. She later compared the emotional impact of the miscarriage to the loss of her father seven years prior.

"My identity has been shaken in regards to who as I am as a mom and human being," Port said in July 2019. "I'm currently in the process of learning to accept that my feelings are valid no matter what they are. Whether or not people feel the same way as me or not. They are my personal emotions that are the result from my own journey."

In February, Port confirmed she and Rosenman "will try again" in the future.

"Last time, I don't think I was ready to have another child, and I had different feelings about the miscarriage," she said on the Being Bümo podcast. "This time, I really connected. I was actually excited and enjoying the pregnancy."

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