Inside Kendra Wilkinson And Hank Baskett's Relationship

Kendra Wilkinson and her former husband Hank Baskett had each achieved fame — Wilkinson through her high-profile relationship with Playboy mogul Hugh Hefner and Baskett through the NFL. While in their 20s, they both had wealth, notoriety, and lives most people couldn't help but be jealous of. However, both were missing that special someone to share their busy worlds with. A chance meeting at the notorious Playboy Mansion put the two beautiful celebrities into each other's orbit. From that initial introduction, Wilkinson and Baskett embarked on a whirlwind relationship, followed by a reality television show, more fame, a growing family, and loads of drama that neither could shoulder. The reality television couple tried to make things work despite the many setbacks they faced but, in the end, it was best for all that they parted ways.

From strange beginnings and showcasing their lives in front of cameras to scandals and divorce that played out in front of the public, this pair has had an interesting relationship from start to finish. Their ups, downs, squabbles, and eventual peace isn't how these two planned life unfolding when they said their "I do's," but the universe sometimes has other directions for people — and it doesn't take into account broken hearts and saddened souls. 

Kendra Wilkinson and Hank Baskett's relationship highlights where they have been, what they've learned, who they are, and where they are going.

Kendra Wilkinson walked down the aisle in a place she was all too familiar with — her former home ... the Playboy Mansion. Before Wilkinson became Mrs. Baskett, she was one of Hugh Hefner's many blonde beauties, living under his roof and enjoying his company. While some might find it strange she chose to marry in the home of her former, much older boyfriend, others saw it fitting, as Wilkinson, Hefner, and the other girlfriends at the time, Holly Madison and Bridget Marquardt, were like family for many years. 

Everyone looked comfortable and at ease on Wilkinson and Hanks Baskett's big day, dancing the night away and celebrating the newlyweds. Per People, Madison and Marquardt even served as bridesmaids to Wilkinson. Marquardt revealed to Us Weekly that the civil ceremony was very emotional. She got chills and fought back the tears, and even Wilkinson's former flame's eyes welled up. Madison was also moved by the couple's love and began crying. All were in support of the marriage, with Wilkinson honoring Hefner with the second dance of the evening. They floated around the dance floor to "As Time Goes By," a tune from Hefner's favorite film, "Casablanca" (via Glamour).

There certainly weren't feelings of longing or jealousy on the part of Hefner as he watched his young former girlfriend become someone else's wife. No way. The late mogul told E! News, "I could not be more delighted. This is one of the happiest days in one of the happiest places on earth."

The timeline for Kendra Wilkinson and Hank Baskett's romance was a fast-tracked one, even by celebrity standards. They first met during the annual Playboy golf tournament, where both were looking for a hole-in-one, but neither was exactly searching for love. On the couple's ninth anniversary, Wilkinson celebrated her husband in a now-deleted Instagram post, saying they met on the golf course, and right then, she knew Baskett was meant to be hers (via E! News). It seems it was love at first sight for both parties, and their relationship progressed rapidly from there.

According to InTouch Weekly, the two dated for only six months before announcing their engagement in November 2008. Baskett proposed to Wilkinson atop the Seattle Space Needle in front of both of their families, E! News reported at the time. It wasn't long before Wilkinson and Basket learned they would become not only man and wife but also parents, as Wilkinson was pregnant with the couple's first child.

The ecstatic pair revealed their big news to E! News in June 2009. "Hank and I are thrilled to announce that we are expecting our first child together," Wilkinson said. "We are touched by the outpouring of support by our family, friends, and fans." Two weeks after telling the world they had a bun in the oven, they were wed at Wilkinson's former residence, the Playboy Mansion. 

In the first few years of Kendra Wilkinson and Hank Basket's relationship, tons of change took place — and in a short span of time. As such, the young lovebirds had to adjust to many firsts. Both went from single, successful 20-somethings to spouses and parents seemingly overnight.

Following the birth of the pair's first child, Wilkinson experienced bouts of depression for years, which impacted the couple's relationship. The reality star told InTouch Weekly, "I felt like I was in a black hole. I had so much anger inside. I'd lock myself in my closet to cry and scream." Wilkinson had experienced depression before, as she revealed in her memoir, "Sliding Into Home." This time, however, the stakes were so much higher. Now, she had a child and husband in the picture.

Wilkinson, who candidly discussed this period of time with InTouch, explained that her depression led to constant fighting between her and Baskett. The two started sleeping in separate beds while discussing a possible split. Wilkinson eventually healed, telling Self magazine that postpartum depression is real, scary, and requires professional attention. She offered sage advice on the matter: "You shouldn't vent and open up to your husbands, your boyfriends, your friends, because they're not professionals. They don't know the right thing to say to you, and putting them in that position is tricky."

The tricky part of any long-term relationship is fusing two completely different humans into one similar trajectory. When you are one-half of a couple, you can have your own hopes, dreams, goals, and aspirations, but as part of a unit, your finish line in life has to somewhat jive with that of your partner. Kendra Wilkinson and Hank Baskett might have been too different in their wants and needs to make their marriage work. She had already tasted fame, fortune, and a lavish life thanks to her former role as Hugh Hefner's girlfriend and reality television star status on "The Girls Next Door." Baskett, on the other hand, was a celeb, of course, but playing in the NFL meant his life wasn't on display in the same way as Wilkinson's.

One of the couple's most significant hurdles was never being able to level up. A source reportedly close to the former couple claimed to People, "He just ended up being such a dud, and it frustrated her. They never grew to the next level. It was always her driving the career and fame and money. It stopped working around 2014, and they held on, but that's when it went downhill."

Proof of the two wanting different things in life is evident in their post-divorce actions. Baskett has stayed private following his NFL retirement, choosing to live his life off-camera. Meanwhile, Wilkinson has continued to work in reality television, focusing on highlighting her new career in "Kendra Sells Hollywood."

Kendra Wilkinson and Hank Baskett found themselves in the midst of one of the most talked about celebrity cheating scandals of modern times, and while this incident wasn't the only issue in the already fraught relationship, it might have been the nail in the coffin.

In 2014, just about five years into the marriage, Hank Baskett got caught with his ... errr ... hand in the cookie jar. Baskett was accused of having a fling with model Ava Sabrina London. London revealed sordid details of her alleged romp with Baskett to The National Enquirer and underwent a polygraph test to help prove her claims were legit. A possible cheating situation is painful enough, but the fact that Wilkinson was eight months pregnant with the couple's second child at the time the allegations surfaced became salt in the already gaping wound.

Somehow, the scandal didn't immediately break up the pair, and a year after the allegations surfaced, Baskett explained his side of the story to People. His version of events remains drastically different than London's, and both Wilkinson and Baskett deny that any consensual sexual activity ever took place. What Baskett did own up to was creating a painful situation for his loved ones, saying, "I messed up. I put myself in a bad situation. And everything through me brought pain upon this family." Baskett and Wilkinson put a brave face on for several more years, but a full marital recovery wouldn't be in the cards for them.

Over the course of their almost decade-long marriage, Kendra Wilkinson and Hank Baskett sure did give it their all — and no one can say these two didn't try. They managed to weather her postpartum depression, his cheating allegations, and a leaked sex tape from Wilkinson's early days. But, in the end, the two decided to part ways permanently.

Wilkinson filed for divorce in 2018, citing irreconcilable differences, according to TMZ. She then took to Instagram and, in a since-deleted post (via Life & Style), shared her emotions regarding the dissolution of the union. The reality star and mother of two said she wholeheartedly wanted Baskett to find his happiness again and that the world would continue to see both parents out with their children together as a united front, as there were no hard feelings regarding the split, just sadness at the reality of it all. 

In tandem with news of the split, Wilkinson also announced on Twitter: "Today will be the saddest, scariest day of my life. Today I will have to be the strongest I've ever been. Today, my rebirth begins." Months later, she took to Twitter to tell the world the divorce was official. 

Hank Baskett and Kendra Wilkinson might no longer be husband and wife, but they are still family. The two share a son, Hank Baskett IV,  and a daughter, Alijah Mary Baskett. Their son was born in 2009, and his little sister, Alijah, arrived in 2014.

Learning to co-parent with your ex can be tedious, even in the most amicable of splits, but it looks as if Wilkinson and Baskett have figured out the secret to making their family structure work years after their divorce. Three years post-split, Wilkinson told Us Weekly that everything between the former husband and wife was stable. "We are [in a better place]. Time heals all," the reality star explained. 

Wilkinson also spoke about being a single mama and sharing parental duties with her ex in her revealing on-camera interview with Us Weekly in 2021. While she adores her two children, Wilkinson said she is sure that two babies are more than enough for her. She also shared that parts of single motherhood are especially challenging for her, particularly the amount of time she ends up alone and in judgment by the outside world. She revealed that while co-parenting with Baskett is going well, it's still tough, and she misses her children when she doesn't have them under her roof. In true Wilkinson fashion, she paired the sad aspects of sharing custody with a funny anecdote on how some weeks she can't help but look forward to sending the little rascals off to their father. 

Kendra Wilkinson and Hank Baskett once starred on reality television together but have moved on from their former lives as a married couple. In their quest to transform into the newest and best version of themselves, they have both taken on exciting ventures.

Baskett retired from the NFL in 2011, years before he and Wilkinson divorced, but instead of moving in the direction of game analysis, as many former professional athletes choose, Baskett took up with a video game company. As of this writing, he works with HBCustoms. His Instagram page reflects his devotion to the job as it highlights the company in many posts. 

Wilkinson has made a career of reality television and has appeared on several shows since her early 20s. As a single woman looking to capitalize on her talents in hopes of building onto her already substantial wealth, Wilkinson became a licensed real estate agent in 2020 (via People). She has since merged her new career as a real estate agent with reality television in the Discovery+ hit "Kendra Sells Hollywood." Viewers can watch the former Playboy party girl sport suits and sell properties.

Kendra Wilkinson and Hank Baskett loved, lost, and rose from the ashes, moving forward with co-parenting and new careers. All that seems left for these two is finding new and lasting love. With their split now years in the past, you may be wondering when romance will strike for these two.

As for Baskett, he has stayed silent on most fronts regarding his love life. He did, however, send fans into a frenzy with a Twitter exchange, in which he and someone named Ashley Nicole joked about it being a good night for wine or, in Baskett's mind, an entire wine kind of day! The exchange came off as flirty, and many wondered if Baskett was looking to score a touchdown with a new love interest (via InTouch Weekly).

As for Wilkinson, she told People in late 2021 that she is open to new romances. "Until now, I never really felt ready. But now, I want to explore that other side of me, and I hope to find love again. I want to fill my home with someone else's energy. It will be nice to have that again," she admitted. As of this writing, no one has fit Wilkinson's bill, and until that special person comes along, the reality star feels content with the relationship she is building with herself.