Why Did I Get Married Again? Cast Guide: Who’s Related, Married, Dating, and Broken Up

There’s nothing like a wedding to bring together loved ones, celebrate new and old bonds, and, more than anything else, stir up family drama. In Tyler Perry’s Why Did I Get Married Again?, the union of Jasmine (Armani Greer) and Wesley (Everett Osbourne) promises to do all of the above and then some, which makes sense given  the gorgeous couple’s parents — and their parents’ friends. 

Jasmine is Angela (Tasha Smith) and Marcus’s (Michael Jai White) daughter, and Wesley is the son of Roselyn (Taraji P. Henson), who is new to Perry’s franchise but a long-time friend of the group. Of course, Terry (Tyler Perry), Diane (Sharon Leal), Sheila (Jill Scott), Troy (Lamman Rucker), and Mike (Richard T. Jones) wouldn’t miss the Lake Como, Italy celebration, with their own kids — Marcus Jr. (Da’Vinchi), Kenya (Laya Deleon Hayes), T.J. (Jaden Michael), and Denver (Charles L. Smith) — in tow.

From the second guests arrive at the welcome dinner, however, salacious secrets emerge, and old behaviors — remember what happened in Why Did I Get I Married? and Why Did I Get Married Too?resurface, threatening to derail the weekend festivities. It quickly becomes clear that this already very entangled group is even more complicated than they first seem. And when a few outsiders — Nick (Derrick A. King) and Regina (Sydney Winbush) — get tossed into the cauldron of drama, the gang’s antics are lit aflame. 

Struggling to keep up with who is related to whom, and who is sleeping with whose ex? Keep reading to get acquainted with these wedding guests in Tyler Perry’s Why Did I Get Married Again?, now streaming. 

 

The Adults

About the Character

Wife: Dianne 

Kids: T.J. and Kenya 

Terry is a pediatrician whose medical skills have come in handy more than once during their group trips. Terry often anchors the group with his calm and sense of perspective.

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Woman in a blue and white dress standing outdoors at night, with stone walls, greenery, and string lights in the background, looking to the side with a serious expression.

About the Character

Husband: Terry 

Kids: T.J. and Kenya 

Diane is an ambitious litigator who has worked hard to find the balance between family and work. She and Terry have faced their fair share of ups and downs, but these days they’re very steady — almost too steady. 

Previously In

Dreamgirls, Addicted 

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Amateur

Woman in a vibrant blue dress with feathered sleeves smiling and gesturing with arms open at an outdoor evening event, surrounded by other guests in formal attire and lush greenery in the background.

About the Character

Husband: Marcus

Kids: Marcus Jr. and Jasmine

For years, Angela ran a successful haircare line. She and her husband Marcus have always had a fiery relationship — her signature shriek “Marcus!” is a franchise mainstay — but when the movie opens, they claim they haven’t fought in years. After all, they’ve been a little preoccupied as mother and father of the bride-to-be. 

Previously In

The Whole Ten Yards, Couples Retreat


Man with a short beard and mustache wearing a dark shirt stands indoors by a window with tan curtains, looking slightly confused or concerned. Other people are partially visible in the frame. Warm, soft lighting.

Michael Jai White

as Marcus

About the Character

Wife: Angela

Kids: Marcus Jr. and Jasmin

A former football star, Marcus is threatened by his future son-in-law Wesley’s (Everett Osbourne) buzzy athletic future. Marcus will do whatever it takes to prove he’s still got it to the younger generation — including showing off in the weight room.

Previously In

Black Dynamite, The Dark Knight


Woman in a colorful, patterned dress standing outdoors in front of a dark vehicle, smiling and holding a camera, with a large, multicolored woven tote bag on her arm.

About the Character

Husband: Troy 

Ex-husband: Mike

Kid: Denver 

These days, Sheila has her hands full taking care of her mother, who is sick with Alzheimer’s disease. And if that wasn’t enough to worry about, she inadvertantly gets entangled in an argument between bride and groom.

Previously In

The No. 1 Ladies’ Detective Agency, First Wives Club


Middle-aged couple warmly embracing in a cozy, well-decorated living room with soft lighting and artwork in the background, conveying comfort and affection.

Lamman Rucker as Troy (right)


About the Character

Wife: Sheila

Kid: Denver

Troy runs a grass-cutting company alongside his wife Sheila. The couple met in Colorado during Why Did I Get Married? — so natural,y their son’s name is inspired by the snowy state. 

Previously In

N-Secure, The Greatest Song


Man sitting at a decorated dinner table with floral arrangements, wearing a patterned shirt, indoors at night with string lights blurred in the background.

About the Character

Ex-wife: Sheila

Kids: None

Girlfriend: Regina

Because of how he’s treated Sheila over the years, Mike is not beloved by the group, but always begrundingly included. He turns up with a much younger girlfriend, Regina — who happens to have unexpected ties to the celebration. Somehow, Mike’s younger partner has inexplicably helped him regrow his hair.

Previously In

Event Horizon, Phone Booth


Smiling woman in a blue denim jacket with pearl accents stands indoors, in front of a wooden bookcase filled with books, while two people stand behind her in a well-lit room.

Taraji P. Henson

as Roselyn

About the Character

Ex-husband: Harvey

Boyfriend: Nick

Kid: Wesley

Roselyn has made a killing in real estate and runs a multimillion-dollar company. While she hasn’t gone on vacations with the group in the past, she’s a long-time friend with many points of overlap — now including her son Wesley marrying Marcus and Angela’s daughter Jasmine.

Previously In

The Curious Case of Benjamin Button, Hidden Figures

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STRAW

The Kids 

Woman with long dark hair in a blue striped shirt standing indoors, looking serious and focused, with part of another person visible beside her and a neutral background.

About the Character

Parents: Marcus and Angela 

Fiancé: Wesley

Best Friend: Kenya 

Jasmine is the blushing bride of Why Did I Get Married Again? She’s spent her life looking up to her parents’ relationship and those of their closest friends. Now that she’s embarking on her own marriage journey, it’s time for her to learn some hard truths. 


Smiling man in a white tuxedo and sunglasses dancing at an outdoor celebration, surrounded by people in formal attire, with sunlight and a stone wall in the background.

Everett Osborne

as Wesley 

About the Character

Parents: Roselyn and Harvey 

Fiancée: Jasmine

Best Friend: Marcus Jr.  

Wesley is the other half of the engaged couple that brings everyone together for Why Did I Get Married Again? The football player is quickly approaching the athletic records of his soon-to-be father-in-law, Marcus. But Wesley has bigger issues off the field — namely his estranged relationship with his mom, Roselyn. Can this family come together in time for Wesley and Jasmine’s wedding? 

Previously In

Chicago Fire, Sistas


A stylish man stands outdoors at night with his arms crossed, wearing a color-block polo shirt, gold jewelry, and a watch, with a confident expression and blurred greenery in the background.

Da’Vinchi

as Marcus Jr. 

About the Character

Parents: Marcus and Angela 

Ex: Regina

Best Friend: Wesley

Marcus Jr. takes after his father in more ways than his mom, Angela, would like. The problems only multiply when his ex-girlfriend Regina becomes a surprise addition to the wedding guest list. 

Previously In

Where There’s Smoke, BMF


Young woman with curly hair styled half-up, wearing a blue and white striped dress with lace trim, smiling in an outdoor evening setting with a dark blurred background.

Laya Deleon Hayes

as Kenya 

About the Character

Parents: Terry and Diane  

Best Friend: Jasmine 

Jasmine and Kenya grew up together, and Kenya is more than happy to support her day-one BFF on Jasmine’s big day — even if that means protecting a few secrets along the way.   

Previously In

The Equalizer, Snoop 


Young man in formal attire with a red blazer, white shirt, and dark tie standing at an indoor event. Other people in formalwear are in the background, the setting appears social and lively.

About the Character

Parents: Terry and Diane  

A truth teller with an eye for extreme camera zooms, T.J. is the youngest of the crew. He may still be learning the ways of the world, but he always gets invited to the club with the rest of his honorary cousins. 

Previously In

Colin in Black & White, Harlan Coben’s Shelter

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Colin in Black & White
The Get Down

A man sits thoughtfully with his hand on his chin, wearing a patterned jacket and wristwatch, in an indoor or nighttime setting with a dark background.

Charles L. Smith

as Denver

About the Character

Parents: Sheila and Troy   

Much like his sweet parents, Denver helps keep the peace as drama stirs throughout the group. 

Previously In

All American, 9-1-1


SPOILER ALERT

This article contains major character or plot details.

Somewhere in Between

Man in a white shirt sitting at an outdoor restaurant table with food, with blurred people and greenery in the background, enjoying a casual meal.

About the Character

Girlfriend: Roselyn

Upon arriving in Italy, the entire group meets Roselyn’s new boyfriend, Nick. The 27-year-old student also happens to be her son Wesley’s former middle school tutor. Unsurprisingly, Roselyn has kept her relationship hidden from her opinionated friends. But now the secret is out and clearer than ever in the Lake Como sunlight. 

Previously In

Run the World, The Game


A smiling couple poses for a selfie beside a bright green sports car outside a modern building with glass windows, surrounded by greenery and reflections of trees.

Sydney Winbush as Regina (left)


About the Character

Boyfriend: Mike 

Ex: Marcus Jr. 

At the beginning of Why Did I Get Married Again?, Marcus Jr. is in a foul mood over a recent breakup. His attitude only worsens when Regina shows up to the festivities on Mike’s arm. Regina is Marcus’ ex. Despite their split — and Regina’s new relationship with an older man— it’s unclear whether she and Marcus Jr. can keep their hands to themselves. 


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