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To All The Women Malcolm Winters Has Loved Before on The Young and the Restless

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That smile. Those abs. It's really a wonder Malcolm Winters (Shemar Moore) didn’t have more lovers during his time in Genoa City. Here’s a look back at the many times Malcolm tried and failed at that thing called love on The Young and The Restless.

Vivica A Fox

Stephanie Simmons

Played by the timeless Vivica A. Fox, Stephanie Simmons was a colleague of Drucilla’s (Victoria Rowell) at Genoa City Memorial. Dru set Malcolm up with Stephanie, but they didn’t last long.

Her tough schedule as a nurse was the cause of their split. Stephanie soon left town, and Malcolm had an eye for another woman.


Drucilla Barber Winters

We always want what we can’t have. This was the case for Malcolm when it came to Drucilla. She was his brother Neil’s (Kristoff St. John) woman, but he always yearned for her.

One night, Dru took too much cold medicine and Malcolm visited her. Unable to tell Malcolm was not her husband, Dru slept with him! After the deed was over, Malcolm felt terrible. He ran to Dru’s sister Olivia (Tonya Williams), and told her everything that happened.

Dru swore Malcolm to secrecy regarding their roll in the hay, and he agreed. However, in true soap opera fashion, Drucilla soon discovered she was pregnant. She wasn’t sure if Malcolm or Neil was the father. Fortunately, Malcolm agreed to let Neil believe he was the child’s father no matter what.

Years later, Malcolm and the rest of Genoa City found out he was actually Lily’s (Christel Khalil) father, but Neil had raised the child. The status quo didn’t change, even though the truth was out. You can’t win them all Malcolm.

Keesha Monroe

Keesha Monroe

Malcolm, a successful photographer for Jabot Cosmetics, was promoted to the top spot after Blade (Michael Tylo) died. During a break from taking pictures, Malcolm visited Gina’s place and saw Keesha Monroe (Jennifer Gatti). She was a very beautiful woman, and the two hit it off. They dated for a few months, and then the grits hit the fan.

It turned out, Keesha had an affair with Olivia’s husband Nate (Adam Lazarre-White). To top it all off, Keesha was a HIV positive, and the disease had developed into AIDS.

Instead of being irate, Malcolm made Keesha comfortable as she slipped away. He even fulfilled her dying wish and gave her a beautiful wedding. After the couple exchanged their vows, Keesha passed away. I get teary-eyed just thinking about it.


Olivia Barber

As Malcolm grieved for Keesha, he found his way into the arms of Dr. Olivia Barber Hastings. Olivia’s husband, Nathan Sr., had just died in a car accident. Malcolm’s  warm feelings for Liv soon turned to love.

At first, she was hesitant to move on with him. Olivia was in love with Malcolm’s brother Neil, husband of her sister Drucilla.

Dru called Olivia out on wanting Neil all to herself. Olivia shut down her sister’s suspicions by marrying Malcolm.

Malcolm, Olivia and little Nate were a strong family unit for about two years, until singer Callie Rogers blew into town. She caused a hurricane of hurt for Malcolm and Olivia in more ways than one.

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Callie Rogers

Callie Rogers (Siena Goines) was a former flame of Malcolm’s, who couldn’t forget the past. Malcolm was married to Olivia when Callie first arrived in town, but things changed quickly.

Callie and Malcolm kept ending up in compromising positions, leaving Liv to lose trust in Malcolm. The lack of trust in the marriage caused the couple divorce.

Malcolm and Callie soon rekindled their old flame, and Malcolm moved in with her. However, things took a downturn when Malcolm discovered Callie was secretly married to her manager Trey Stark (Rodney Van Johnson). Trey refused to let Callie go, even after Malcolm asked Callie to marry him.

Malcolm soon washed his hands with Callie and had a fling with Dru. Of course, it didn’t last long.


Alex Perez

Always the ladies man, Malcolm set his sights on high-powered attorney Alex Perez (Alexia Robinson). She came with commitment issues, but Malcolm broke through all of her barriers.

The two eventually moved in together and talked about marriage. However, a familiar face became a huge problem for the couple: Neil.

Alex and Neil began working together and slowly fell in love. The day Neil wanted to confess his feelings, Malcolm asked Alex to marry him. She agreed, but delayed the marriage for months, due to her feelings for Neil.

Around this time, Neil’s best friend Ryan McNeil (Scott Reeves) was murdered in cold blood by his ex-wife Tricia Dennison (Sabryn Genet). The tragedy caused Neil to hit the bottle. He even drunkenly admitted his feelings for Alex to Malcolm.

Malcolm quickly confronted Alex to find out if she shared Neil’s sentiments. Alex swore Neil was alone in his feelings. She informed Malcolm she wanted to get married right away.

Before they could marry, the couple and Neil had to do a business photo shoot in Kenya. Malcolm accidentally overheard Neil and Alex discussing their feelings for one another. A distraught Malcolm left before Alex told Neil she was in it to win it with Malcolm.

Malcolm later returned and confronted Neil. Malcolm punched Neil for stealing his woman, and stormed off to get ready for the photo shoot.

On the way to the location, Malcolm was involved in a terrible car accident. The car fell off a collapsing bridge into the water. Malcolm managed to get out of the car and rescue someone else. However, the rest of bridge fell onto to Malcolm, and he was declared missing…for three years.


Sofia Dupre

Malcolm (Darius McCrary) returned to Genoa City in 2009 as a whole new person (cue the drum and symbol). He immediately visited Lily, who was battling cancer. While at the hospital, Malcolm and Neil decided to end their feud for Lily’s sake. Malcolm felt it would be best to stay in town for a while and look after Lily.

While catching up with his family, Malcolm kept talking about having a fiancée. No one knew who the mystery woman was.

Malcolm had a deal with underhanded businessman Tucker McCall (Stephen Nichols) to spy on dealings at Restless Style and Newman Enterprises for him. Malcolm wanted out, but Tucker threatened to out his involvement if he did.

After their confrontation, Sofia Dupre (Julia Pace Mitchell), Tucker’s right hand woman and Malcolm’s mystery fiancée, showed up in town.

Neil initially didn’t like Sofia. The keyword in that sentence is initially. As Sofia got to know the family, Neil began to lighten up.

However, Sofia’s business dealings with Tucker caused a rift in her relationship with Malcolm. She lied about knowing Cane (Daniel Goddard) was embezzling money from Tucker, which inadvertently led to Cane’s “death”. Tucker fired Sofia, and Malcolm felt he made the right decision.

Sofia was crushed, and found solace with Neil. More specifically, she felt better after screwing Neil on the couch at his apartment! Malcolm showed up wanting to make up with Sofia.

Sofia reconciled with Malcolm and the two were married. On their honeymoon, Sofia discovered she was pregnant. She wasn’t sure if the child was Malcolm's or Neil’s.

Sofia plotted with Olivia to tell Malcolm an early due date. However, a potential medical crisis forced her to tell Malcolm the truth.

Malcolm separated himself from Sofia until the baby was born. A DNA test concluded Neil was the father. Malcolm soon divorced Sofia and skipped town.

Which one of Malcolm’s loves were your favorites? Sound off in the comments!