How Many Times Has Kimberly Stewart Been Engaged?

One of the more popular children of rock legend Rod Stewart is her daughter with model Alana Hamilton, Kimberly Stewart. Per Hollywood Life, Kimberly is a socialite and model who has dipped her toes into the acting world by appearing in the 1998 series "Pacific Blue." She was then cast in the sitcom "Undeclared" in 2001 and was later featured in the films "Homecoming" and "Lost Lake" (per IMDb). In 2015, Kimberly joined her Hollywood royalty family in the reality docu-series "Stewards and Hamiltons." The show aired for eight episodes on E! channel before it was ultimately canceled by the network, according to The Hollywood Reporter.

Since then, Kimberly has mostly spent her life far away from the spotlight. She founded her own luxury lifestyle company called The Realm and focused on raising her daughter Delilah with actor Benicio del Toro. "I just wanted to be with her all the time. I've been a stay-at-home mother since she was born, and I've loved every second," she told Hello! Magazine in 2015. Even so, Kimberly has been the subject of many headlines in recent years all because of her tumultuous dating history. Since she split with Benicio in 2011, the blonde American beauty has been involved in a string of high-profile relationships, three of which almost led to marriage. But what happened? Why was she never married? And more importantly, who are these men who almost married Kimberly Stewart? 

Kimberly Stewart was engaged three times

Kimberly Stewart was first engaged to musician Cisco Adler. Per The Sun, the couple dated for three years before getting engaged and eventually calling it quits in 2005. She then briefly dated actor Scott Canaan before moving on with "Laguna Beach" alum Talan Torriero. The couple was barely together for two months when they announced their engagement to the public, surprising many fans and even Stewart's mother Alana. "It definitely took me by surprise," she told People (via Reality TV World). "She's an impulsive girl. What can I say?" However, they also ended up calling off wedding plans after realizing that "it was just too soon to enter into a lifelong commitment." A representative for the two said in a joint statement, "It is better to have a brief engagement than a short marriage. The couple continues to share their time together and remain open to whatever the future may hold."

Stewart's most recent engagement came just this February, to film producer Jesse Shapira whom she has been dating since March 2019, per The Daily Mail. After three years together, Stewart announced that they were engaged via a social media post that showed off her huge diamond engagement ring. "Forever," she simply captioned the photo, followed by a heart emoji, per People. However, it didn't take long before she removed the post from her Instagram feed, indicating that she and Shapira have also called off their engagement and are no longer together.

Who is Kimberly Stewart dating now?

Following her split from Jesse Shapira, rumors swirled that Kimberly Stewart was dating "Keeping Up With the Kardashians" star and Talentless founder Scott Disick. The two, who were first linked back in 2015, ignited speculation of a romance after they were spotted out together last May. They continued to be seen together on multiple occasions until a source confirmed to Us Weekly this month that the two were indeed an item. 

Though still pretty casual, Stewart and Disick have reportedly been "dating for months" and are "really into each other", according to the insider. After several years of just being friends and hanging out in the same circle, the pair decided to finally give love a shot, and have now been "getting to know each other" outside of their years-long friendship. Meanwhile, another source who spoke to The Hollywood Life claimed that Disick's ex-wife Kourtney Kardashian totally approves of Stewart as Disick's new girlfriend. "Kourtney has known Kimberly for many years and she actually thinks this is a good match for Scott," the insider told the outlet. "She knows that Kimberly is a good person and an excellent mother." Aside from this, Kardashian also thinks that the two make a "really cute couple", according to the same source. "She totally supports this. They have her blessing," they added.