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When Adrienne Bailon was just sixteen years old back in 1999, she was performing with a church choir in Madison Square Garden, when pop superstar Ricky Martin showed up and asked for the four best singers in the group. As it turned out, Bailon was one of the four elected, and she ended up singing backup later that night for Martin in his show that was part of his Livin’ La Vida Loca tour.

This performance was the first step towards an unexpected career in music – something that she had always dreamed about, but never thought to be realistic – and it resulted in Bailon putting her plans of becoming an obstetrician on hold.

She went on to become a founding member of 3LW and The Cheetah Girls, had an acting career in TV and movies, starred in her own reality series, and now co-hosts a syndicated talk show.

Bailon’s personal life has also made headlines, especially when she started dating Rob Kardashian back in 2007 and appeared as his girlfriend in eight episodes of Keeping Up With the Kardashians. The two dated for two years but broke up in 2009 when Kardashian admitted to cheating on her.

The Manhattan native eventually moved on and started dating gospel musician Israel Houghton in February 2016, and just six months later the couple was engaged to be married. They eventually tied the knot in November of that year.

From being part of a girl group to a talk show co-host and step-mom, the past two decades have seen Bailon go through a lot of changes, and the camera has been following her every step of the way.

20. More Of The Real

Bailon was all smiles when she found out that her talk show The Real was coming back for two more seasons. The show – which Bailon hosts with Loni Love, Jeannie Mai, and Tamera Mowry-Housley – is a daily hour-long girls gabfest about topics ranging from the ladies’ personal lives to current news, fashion, beauty, and relationships.

The Emmy-nominated show is currently in its fourth season and claims to bring a fresh point of view and youthful energy to the traditional daytime talk show format.

Bailon thanked fans for the show’s two-season renewal and wrote on her Instagram that she was screaming at the top of her lungs and saying God is real. She also was grateful that fans didn’t just hear her and her co-hosts’ words, but also truly heard their hearts.

19. Bailon's Big Break

She may have already been part of the girl group 3LW, but it was when Bailon became part of The Cheetah Girls in 2003 that things really took off for the young singer/songwriter. Both Bailon and her 3LW group mate Kiely Williams signed on to be a part of the Disney Channel film about a four-member female singing group.

The movie was a ratings success, and the soundtrack debuted at number 33 on the Billboard charts and became certified two-time platinum – meaning it sold over two million copies.

According to OK! Magazine, the group didn’t just focus on music but also had a line of clothing, perfume, a video game, and their own line of dolls.

The group disbanded in 2012, and they currently have no plans for any kind of reboot, because, as Bailon shared, she doesn’t want to do anything that “would make it whack.”

18. Sunday Brunch

When Bailon married Houghton – a man 13 years her senior – she became stepmom to his three children, Lillie, Sonny, and Mariah. Houghton was married for over twenty years to his first wife, Meleasa. There was a bit of controversy when Bailon and Houghton began dating because he had announced his separation from Meleasa just one month earlier.

However, Houghton claimed their marriage had been over for a long time before they announced their separation, and Bailon had nothing to do with the end of his marriage.

The Grammy-winner did admit to having an affair while he was married, and that did contribute to the crumbling of the relationship. It was a shock to his Christian fans because the gospel artist strayed from a marriage that lasted more than two decades.

17. Keeping Up With Bailon

The two-year relationship between Bailon and Rob Kardashian was a popular one during the early years of Keeping Up With the Kardashians, but it ended because he cheated, a fact that he admitted on the show.

According to Life & Style, Bailon says that she was always faithful to Kardashian after he claimed that he had an ex-girlfriend who cheated on him. Bailon says that Kardashian was not referring to her, but she couldn’t speak for anyone else.

Bailon got into a Twitter war back in 2014 with Kardashian’s sisters, and in an interview, she said that it was hurtful to her career to be stuck with the Kardashian label, but she realized it was too late.

16. Girl Power

Bailon seems to be embracing life as a wife and stepmom of two girls and a boy, and the holidays appear to be one of her favorite times of the year. She and her stepdaughters enjoyed their reindeer onesies just four days before Christmas at their home in Bel Air.

While Bailon started dating Houghton, his oldest daughter Mariah announced her engagement to Byron Rideau. 22-year-old Mariah met her husband at church, and the two were friends for years before they began dating. She wanted to date for one year before they got married, and that’s exactly what they did.

Milan, or Lillie, is the younger daughter who has become popular on Instagram posting photos of friends and family. The 14-year-old already has over 10,000 followers.

15. Disney Star

With their first movie being such a success, The Cheetah Girls decided to film a sequel, and The Cheetah Girls 2 ended up being the highest-rated original movie ever on The Disney Channel. It even beat out the premieres of the High School Musical movies.

The movie’s soundtrack debuted on number five on the charts and went on to sell more than one million copies. The single Strut – in which Bailon sang lead vocals – ended up being their most successful song and peaked at #53 on the charts.

The group, minus Raven-Symone, also recorded a non-soundtrack studio album called TCG, and it featured the single Fuego, which had a video that The Disney Channel played in heavy rotation.

14. Keeping The Faith

Bailon’s faith has always been a big part of her life, and she started her career by singing and acting in church. She ended up marrying a big star in the Christian music world, with Houghton’s group Israel & New Breed winning six Grammys over the years.

In 2007, he won Best Traditional Gospel Album for Alive in South Africa, and in 2015 he won Best Gospel Album for Covered: Alive in Asia.

He is also a worship leader at Joel Osteen’s Lakewood Church in Houston but did take an indefinite leave of absence to tour and travel with Bailon.

There were rumors that Houghton lost his job at the church amid the rumors of his cheating, but Lakewood denied those reports and said he still works for them.

13. Get Over It

When Bailon and Kardashian broke-up, she found an unlikely source of support and comfort: his sister Kourtney Kardashian. Around the same time, Kourtney had briefly broken up Scott Disick, and the two were dealing with heartbreak at the exact same time.

But, according to Us Weekly, Bailon once revealed during an episode of The Real that she and Kourt had different coping mechanisms.

“She was so much fun,” Bailon recalled. “I was definitely more the sad one crying at home and she was like, ‘No girl, we are going to go out. We’re going to hit the clubs in Hollywood. We’re going to have so much fun!’”

When her co-host, Loni Love, pointed out that Rob cheated on her during the relationship, Bailon called it “old news.”

12. I'm In Love With A Church Girl

In 2013, Bailon starred in the highest-grossing independent film of the year, I’m In Love With A Church Girl. The Christian drama is the story of drug dealer Miles Montego (Ja Rule) who meets Christian girl Vanessa (Bailon) at a mutual friend’s house and they start a relationship.

When Miles tells Vanessa he wants to change his life, she accepts it and believes that he will begin to have faith in God. However, the couple faces obstacles including a DEA investigation, a parent’s death, a car accident, and a coma.

The Christian community received the film relatively well, with one reviewer saying that the film delivered the Christian message with authenticity and respect. The movie also performed higher than expected, earning a per screen average of over $2,000. The box office estimates were at $1,000 per screen.

11. Godparents

Even though Bailon and Kardashian broke up almost a decade ago, the two are still connected in a special way. When they were dating, they shared the responsibility of being Godparents to one of her family members.

According to BET, Bailon shared on The Real that she and Kardashian were Godparents to one of her cousins but once they broke up they never thought about it again.

She added that her family didn’t seek him out because people move on and things change. Plus, it would be weird since the two are no longer together.

The former couple traveled to North Carolina for the baby’s christening, and Bailon says it was a great moment that they once shared, but she doesn’t regret the way things ultimately went.

10. Fresh. Organic. Local.

Bailon loves her farm-to-table food, and she shared with her Instagram followers an outing with Lillie to Malibu Farm. The location features two restaurants with a casual service counter at the end of Malibu Pier and a full-service restaurant and bar at the beginning.

The locally-owned small business sources all of their ingredients from local farmers, with local breads coming from nearby bakeries.

Bailon and her husband’s youngest daughter seem to have bonded quickly, and the two often share pics on social media of themselves enjoying a day out or just relaxing together at home. It’s pretty cool that the two of them get along so well since 14-year-old girls can be a challenge for a step-parent. But, these two seem to have a special relationship.

9. That's So Raven

Nine years after Bailon portrayed Chanel “Chuchie” Simmons and Raven-Symone played Galleria “Bubbles” Garibaldi in Cheetah Girls 2, the two reunited on an episode of The Real, and the duo took a trip down memory lane and shared some old dance moves from their Cheetah Girls days.

They also talked about some of their more questionable fashion choices and how Bailon used to apply mascara.

Symone was part of the first two Cheetah Girls movies but didn’t participate in the third due to a scheduling conflict with the film College Road Trip and the recording of her fourth studio album. The That’s So Raven star also was not part of the real-life Cheetah Girls group that toured the country and recorded their own albums, opting instead to focus on her solo career.

8. C'est La Vie

After breaking up with Kardashian, and before she started co-hosting The Real and married Houghton, Bailon and her bestie Julissa Bermudez starred in Empire Girls: Julissa and Adrienne, a reality show that premiered on the Style Network in 2012.

The two friends met on the set of the 2006 movie All You’ve Got, and the show followed them as they tried to get big breaks in the entertainment industry. Even though Bailon had a successful career with The Cheetah Girls, her goal was to become a successful solo artist, while Bermudez pursued a career as a talk show host.

In addition to going after their career goals, they both were also looking for love while putting their relationships with high-profile exes behind them. The show lasted one season.

7. Ruining Her Fierce Image

Bailon won’t let her husband watch any of The Cheetah Girls movies because she is afraid if he does, he will no longer find her attractive. According to E! News, the 34-year-old told her co-hosts on The Real that she never thought the first movie would be a hit.

She explained she was an 18-year-old playing 16, and Disney wanted her to look young and fun at a time that she was starting to grow into herself and date more. Bailon said once she finished the movie, she never wanted any guy to see it.

Even though it was “fun” and “amazing” to make the movies, she still refuses to let Houghton watch any of them because she was really young.

6. Christmas At The Apollo

Bailon appeared on the Showtime at the Apollo Christmas Special last year along with Snoop Dogg, DMX, Boyz II Men, and Fifth Harmony, and each of the artists performed some of their favorite holiday songs. Bailon performed the solo This Christmas, but before she made it to The Apollo, she visited the special’s host Steve Harvey on his daytime talk show.

The singer shared a pic on her Instagram of her visit and said she had a great time and was so excited about her appearance on the special. She also took the opportunity to promote her new Christmas album New Tradiciones that featured the song Christmas Worship Medley that she sang with her husband. Other songs included were O Holy Night and Have Yourself A Merry Little Christmas.

5. BFFs

Just because Bailon and Rob parted ways in 2009, it doesn’t mean that she can’t still hang out with his sisters. In 2016, she caught up with Kourtney Kardashian and Kendall Jenner, and she told Us Weekly that is always great to see them because they are amazing girls.

Kourtney shared a pic of the three of them on Instagram while they attended the Ciroc Vodka, Variety & WWD’s Women of Empowerment Brunch at the Four Seasons Beverly Hills and she captioned the pic, “Reunited best friends.”

Jenner posted a pic, too, with the caption, “Cause we are sistersss.”

Bailon says that she thinks they will always be a part of her life. As for Rob, she no longer talks to him, but she did admit that she loved him at one point in her life and she wishes him the best.

4. Becoming Mrs. Houghton

Bailon married Houghton in Paris back in November 2016 – just nine months after they started dating – and in addition to wearing her huge engagement ring, she also rocked a fabulous wedding dress.

The stunning strapless gown featured a plunging neckline and a long lace train that went on for days. She added a long veil to the mermaid-style gown, and she and her new husband posed for wedding pics in front of the Eiffel Tower.

The couple first met on the set of I’m In Love With A Church Girl, where he was a producer, and when she got engaged to former fiancé Lenny Santiago, he sent her a note of congratulations on social media. But, Bailon’s relationship with Santiago didn’t last, and that is when her friendship with Houghton blossomed into a romance.

3. Parting Ways With Kim K.

Even though she remains friends with Kourtney and Kendall, it doesn’t appear that Bailon has the best relationship with Kim Kardashian-West.

Kim didn’t take kindly to the interview where Bailon admitted that being on KUWTK was hurtful to her career, and tweeted, “Funny how she says being with a Kardashian hurt her career yet the only reason she has this article is because she is talking about a Kardashian.”

Bailon said that if she had realized that appearing on the reality show would stick her with the Kardashian label, she would have made a different decision.

But, even though she regrets being on the show, she is happy about all of the good friends she made while dating Rob. During her time on KUWTK, episodes featured her and Rob getting tattoos and his heartbreak when she left to shoot the third Cheetah Girls movie in India.

2. Hollywood Diva

After the breakup of The Cheetah Girls, Bailon signed on with Island Def Jam records to record her debut solo album, and the Confessions of a Shopaholic soundtrack featured her songs Big Spender and Uncontrollable.

But, her solo album never happened, and in 2015, Bailon admitted she never released it because she was scared to fail, and she didn’t like the sound of her own voice.

When she got her solo album deal, things didn’t go as expected. Bailon is a Christian, and when asked about getting involved in the craziness of Hollywood, she said that not everyone is without sin, and her faith in God helped her avoid getting caught up in those things. She was never interested in the party life, but everyone sins in their own way.

1. Failed Set Up

After meeting on a movie set and staying friends for years, Bailon set Houghton up with one of her girlfriends after his marriage ended. After her friend had a date with Houghton, she asked her how things went. Her friend responded that he wasn’t her type.

Bailon was offended by the response, and couldn’t believe her friend didn’t love his dimples, smile, musical talent, and glowing skin – because it doesn’t get any better than that.

Her friend then said, “Why don’t you date him?”

Bailon and Houghton seem to be crazy about each other, and when he asked her to marry him, Houghton posted a pic of the engagement ring on Instagram and wrote that he took a giant leap of faith by asking her to be his wife and to give him a shot at getting it right this time, and she thankfully granted his request.