10 Times Neil Winters Was Oh-So-Unlucky In Love on The Young and the Restless

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The Young and the Restless' Neil Winters (Kristoff St. John) can always get a woman, but can never seem to keep them! Here’s a look back at the many times Neil has tried and failed miserably at this thing called love.

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No.10 Neil Loses Olivia But Gains Drucilla

In 1991, Stanford Business School graduate Neil Winters joined the staff at Jabot as executive trainee. Before long, he found himself wrapped up in a war between two sisters.

Drucilla (Victoria Rowell) and Olivia Barber (Tonya Williams) were always trying to one-up each other. Olivia was a doctor, while Dru was a runaway-turned-Jabot-mailroom-attendant with a very sordid past. Olivia found love with “reformed” criminal Nathan Hastings (Nathan Purdee), which left her struggling sister Drucilla seething.

Dru wanted Nathan for herself, and needed to come up with a way to win him. She told Olivia she had a boyfriend. One small problem, she wasn't seeing anyone! Dru needed someone to play the part — enter Neil Winters.

Dru and Neil did everything they could think of to win their respective loves, to no avail. When Olivia finally learned what they were up to, she quickly wed Nathan.

Dru and Neil were heartbroken, but soon realized they were a much better fit as lovers! Neil supported Dru as she became a supreme ballerina. In turn, she begin having his back as he climbed the ladder at "the Tower of Newman". The rest, as they say, is soap opera history.

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No.9 Malcolm Sleeps With Drucilla

Dru and Neil were happily married when Neil’s half-brother Malcolm Winters (Shemar Moore) showed up in town. Neil and Malcolm always had a strained relationship. Baby bro's obvious crush on Dru only made things worse.

Neil wanted nothing to do with Malcolm, but Dru took a liking to him. She pulled some strings and got him a job as Blade’s (Michael Tylo) assistant at the photography studio.

One night, Malcolm stopped by The Winters’ apartment to find Dru in a cold medicine-induced stupor. Dru, unable to tell Malcolm was not her husband, slept with the chiseled stud ! The duo awoke the next morning and vowed to never tell Neil.

In true soap opera fashion, Dru ended up pregnant. She was unsure which brother was her baby’s father.

Dru thought about having an abortion, but the gynecologist informed her she might never be able to conceive another child, due to a pre-existing condition. Dru ultimately decided to keep the baby and never tell Neil about her infidelity with Malcolm.

Malcolm agreed with Dru’s decision, as did Olivia. Dru and Neil soon welcomed Lily into the world. Poor Neil was left in the dark about his daughter's true parentage until she was practically an adult.

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No. 8 Neil, Malcolm and Alex Perez

Neil and Dru eventually divorced, and Neil excelled at his career at Newman Enterprises. He worked on an important case with Newman attorney Alex Perez (Alexia Robinson), and fell in love with her. The only problem was, Alex was already in a relationship with Malcolm! Alex had deep feelings for Neil as well, but did her best to hide them from Malcolm.

When blonde nut job Tricia Dennison (Sabryn Genet) murdered his best friend, Ryan McNeil (Scott Reeves), Neil began drinking uncontrollably. Malcolm and Alex attempted to help, but Neil refused it.

During one drunken outburst, Neil confessed his feelings for Alex. Malcolm confronted Alex about Neil’s affections, but she swore she didn’t return his feelings.

Flash forward to a healthier Neil, Alex and Malcolm all being sent to complete the late Ryan’s work in Kenya. Alex and Neil got into big argument. She admitted her feelings for Neil, while Malcolm listened outside the room.

Malcolm stormed off before he could hear Alex tell Neil she wanted to be with Malcolm. An enraged Malcolm later knocked Neil’s lights out, and went on to do the photo shoot. Neil's kid brother was involved in an accident on the way to the shoot and presumed dead.

Alex and Neil were too grief stricken and guilty to move on with a relationship. Alex returned home to Minneapolis, and Neil hit the bottle hard this time.

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No. 7 Neil Learns Lily’s True Paternity

It turns out, Malcolm didn’t actually die in Africa. A family found him after the accident and nursed him back to health.

The foxy photographer returned to Genoa City almost three years after his "death", and wanted to reunite with his family. More importantly, Malcolm wanted to know Lily’s (Christel Khalil) true paternity.

He convinced Dru to get another DNA test. Malcolm turned out to be the dad! Dru and Malcolm decided to hide the truth from Neil.

By this time, Lily was a teenager, full of attitude and disdain for her parents. One day she found out the truth about her paternity by eavesdropping on a conversation between Dru and her rival Phyllis Summers (Michelle Stafford).

A distressed Lily attempted to email her boyfriend, Phyllis’s son Daniel (Michael Graziadei), about what she overheard. Unfortunately, she accidentally sent the email to her dad.

Lily tried to get rid of the email before Neil saw it, but was unsuccessful. Lily ended up telling Neil she was not his daughter.

Neil ripped Dru for lying to him since Lily’s birth. Neil and Dru broke up again. This time he found another way to ease his pain besides alcohol — Carmen Mesta (Marisa Ramirez).

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No. 6 Carmen Mesta's Murder

During his separation from Dru, Neil began dating Newman's freelance public relations consultant Carmen Mesta (Marisa Ramirez). Neil’s relationship with Carmen didn't sit well with Mrs. Winters.

Neil's estranged wife followed the new couple on several occasions. She even broke into Carmen's room to play Edward Scissorhands with Ms. Mesta’s wardrobe!

Neil and Dru’s adopted son, Devon Hamilton (Bryton James), contracting meningitis and going deaf put a damper on Neil's fling with Carmen. The Winters decided to get back together for the sake of their family.

Neil eventually opened a jazz club, Indigo. On the club’s opening night, Carmen Mesta was found dead in the alley out back. The Winters were the prime suspects in the case.

Devon was even arrested for the murder, but it was revealed Kevin’s girlfriend, Jana Hawkes (Emily O’Brien), committed the crime. Dru and Devon were absolved of all charges. What a mess Neil created by rebounding Ms. Mesta!

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No. 5 Love Overboard

Dru and Neil’s relationship was stronger than ever in 2007. However, tragic fate—in the form of a three-way fight on a cliff over a phone—stepped in and stole Dru from Neil.

The Winters were overseeing an NVP photo shoot. Dru's best friend Sharon (Sharon Case) and their mutual nemesis, Phyllis, got into a scuffle near the edge of a cliff. Dru stepped in to break them up.

Unfortunately, the women over powered her and they all fell. Dru tumbled off the cliff into the river below, while Sharon hung on to the edge for dear life. Phyllis tried to save her, but wasn’t strong enough. Sharon was found, but Dru was a lost cause.

Neil searched for weeks for her body, but came up empty handed. He soon fell off the wagon again, and drowned his broken heart in a sea of booze.

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No. 4 A Not So Model Marriage

Neil eventually gave up the alcohol for his children. He also went back to work at Newman as co-CEO with Victoria (Amelia Heinle) — yet another woman he'd been unlucky in love with!

During Nikki’s (Melody Thomas Scott) campaign for Senate, he met her campaign manager Karen Taylor (Nia Peeples). Neil helped Karen retrieve her keys from inside her locked car, and the two hit it off.

They began dating and Neil offered Karen Dru’s old job at Newman. She accepted and began changing Dru’s vision. She even donated one of Dru’s famous chapeaux to charity. Neil wasn’t appreciative of Karen’s changes and their relationship became strained.

He soon realized he was being sensitive to all things Dru and apologized. Devon and Lily also weren't pleased with Neil’s new love trying to take Dru’s place.

During the holidays, Karen changed their minds and they accepted Neil’s newest flavor into the family. Karen and Neil faced several challenges in their relationship, but always stayed united, until Devon's "Aunt" Tyra (Eva Marcille) and his "cousin" Sally Sings-A-Lot, er, Ana (Jamia Simone Nash) arrived on the scene.

Neil was wary of Tyra in the beginning, but felt Devon needed to know his biological family. Neil decided to welcome Tyra and Ana into his home.

Karen wasn’t fond of Tyra living with her and Neil, but Neil remained supportive of the down-on-her-luck young woman. It turned out Ana wasn’t Devon’s cousin after all; she his sister, and had a talent for singing.

Ana sang her way into a scholarship at a prestigious school in New Hampshire. She and Tyra left for the school, but soon returned because the cost of living was too high in New Hampshire.

Olivia returned to town and recognized Karen as a former patient. She liked Neil and Karen together, but thought her brother-in-law shared more chemistry with Tyra.

Liv warned Neil he was going to marry the wrong woman. He didn’t listen and married Karen in a beautiful ceremony. Karen wanted to legally adopt Ana. Tyra was not pleased.

When the judge terminated Yolanda’s (Chene Lawson) legal rights to Ana, Tyra wanted to adopt the child. She celebrated by giving Neil a big kiss and confessing her feelings for him!

Karen saw the whole thing, but kept her cool. She later confronted Neil about what she saw, and advised him to get his house in order if he wanted to be with her.

Neil attempted to let Tyra down easy, but ended up banging her on a table at Indigo! They weren’t alone, because Devon walked in on them.

Neil was forced to confess his tryst with Tyra to Karen.Done with his shenanigans, Karen left him. She only returned later to have him sign the divorce papers.

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No. 3 Thy Son Betrays Thy Father

Neil and Tyra carried on a relationship for a minute, until Devon changed everything. He learned Tyra was not his biological aunt, and began having complicated feelings for her.

One day, the two got into a nasty argument, and ended up having sex. Devon’s girlfriend, Roxanne (Tatyana Ali), walked in on them. She quickly broke up with Devon and left it up to him to tell his father.

Devon confessed to Neil he'd slept with Tyra. Neil went ballistic on Tyra for screwing Devon, and she soon left town. Neil just keeps choosing defective models for love.

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No. 2 When Friends Don't Make Good Lovers

Neil Winters and Ashley Abbott (Eileen Davidson) had been friends years, when they finally decided to date. Things were going well, until Ashley began working with music mogul Tucker McCall (Stephen Nichols).

Ashley and Tucker grew closer by the day, and soon hit the sheets on a business trip. Ashley returned home and felt badly for cheating on Neil.

She was going to tell him about it, but Neil broke up with her first! He sold Indigo to Jeffrey (Ted Shackelford) and Gloria (Judith Chapman), and informed Ashley they should just be friends again.

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No. 1 Neil Loses To Devon Once Again

Hilary Curtis (Mishael Morgan) arrived in Genoa City with revenge on the brain. The young woman believed Neil was responsible for her mother’s death, and wanted his entire family to pay!

After being outed as the GC Buzz Mystery Blogger, Neil and Hilary began to work through their issues — but not before she tried to spike his beverage with alcohol! Eventually, Hilary realized the recovering alcoholic wasn't to blame for her mother's demise and the two became friends.

Following her brief, one-sided crush on Jack Abbott (Peter Bergman), Hilary and Neil began dating. Devon wasn’t fond of Hilary in the beginning, but soon took a liking to her. Quickly, he decided he wanted her all for himself!

Hilary wished to stay committed to Neil, but couldn’t deny her growing feelings for Devon. She married Neil to put a stop to those feelings, but it didn’t work.

Being stranded with Devon all night on the side of the road, plus that steamy make-out sesh in the Athletic Club laundry room only intensified "Hevon's" connection. Hilary decided she was finally going to leave Neil for Devon.

As she was leaving Neil a frantic message about "needing to talk", the veteran executive was lying on the floor of the Barbie dream home he'd secretly purchased for his trophy wife — electrocuted! Neil, now blind from the electric shock, currently has his wife's guilty devotion. Will that change if and when he gets his sight back?

Bonus Lost Loves: Sofia Dupree, Harmony (Formerly Yolanda) and Leslie Michaelson.

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Sofia Dupree

Don’t think I forgot about the hot mess from the M all the way down to the S that was Sofia Dupree (Julia Pace Mitchell). Neil even had a child, Baby Ezekiel, er, Moses, with this woman — after he stole her from his brother! Not even a Red Sea-parting child was enough to keep Sofia and Neil together.

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Harmony

Neil was also with Devon’s biological mother, Harmony (Debbie Morgan)—who changed her named from Yolanda—for about five minutes. Mess isn’t even the word for that failed relationship.

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Leslie Michaelson

Neil had a good thing going with attorney Leslie Michaelson (Angell Conwell), but she was afraid of commitment. Leslie broke off her engagement with Neil to marry someone no one had ever heard of. Yep, Neil even loses at love to off screen characters!