18 of Blake Lively’s Most Boundary-Pushing Red Carpet Looks

Juliette Lewis + Brad Pitt

We tend to think of Angelina and Jennifer as Brad’s two big loves, but before them (and Gwyneth) came Juliette Lewis. The two dated for four years when they were both on the cusp of total stardom. These two just might be tied with Johnny Depp and Kate Moss as the most ’90s couple that’s ever existed.

Michael Jackson + Brooke Shields

A budding supermodel and a global pop sensation? It’s kind of a Hollywood match made in heaven, just like Brooke's curls. That dress on the other hand? We’re not so sure.

Matthew Broderick + Jennifer Grey

As much as we’d like to believe Sarah Jessica Parker was Matthew Broderick’s one and only, this couple makes a lot of sense. The two were both the main characters in epic teen ’80s movies – we’ll just forget about the fact that they played brother and sister in one of them…

Jake Gylenhaal + Reese Witherspoon

Dang, why didn’t this couple work out again? Oh right, probably because that much wonderfulness packed into one couple would make the world explode. But they sure did look good together!

Drew Barrymore + Corey Feldman

Feldman once said that his first date with Drew was arranged by her mother when she was 10 and he was 14, because apparently Barrymore had a huge crush on him. They later dated briefly (this time for real) in 1989, when Drew was a teenager. Unfortunately, he was heavily into drugs during that time and she was trying to stay sober after multiple stints in rehab, so it didn’t last long.

Winona Ryder + Christian Slater

Here’s to hoping this relationship ended a little more amicably than it did for their Heathers characters.

Julia Roberts + Kiefer Sutherland

It was supposed to be one of the biggest Hollywood weddings ever, and then all of a sudden, Julia called it off. Tragic. At least we have this red carpet moment to remember the couple by.

Stacy Keibler + George Clooney

Now that Amal is in the picture, it’s hard to imagine George with anyone else. But before that British vision of elegance came Stacy Keibler, the stunning professional wrestler and George’s beau for two years.

Who’s your favorite throwback red carpet couple? Share with us on Twitter @BritandCo.

Did You Know This Fun Fact About the SJP & Matthew Broderick?

Sarah Jessica Parker and Matthew Broderick have known each other since 1991 — that's over 30 years! They've known each other and been married since 1997. SJP and Matthew Broderick also share three kids together whose names are James, Tabitha, and Marion. We just love their love and can't wait to tell you all about it below so keep reading!

A Full Relationship Timeline of Sarah Jessica Parker And Matthew Broderick's Love Story

November 1991/January 1993 — Sarah Jessica Parker and Matthew Broderick Meet

The two actually met through Parker's brothers who ran a local theatre in New York City. SJP was visiting the theatre to see her brothers' play and Broderick had recently directed a play at the very same theatre. The two met and a couple months later, Broderick sweetly left her a voicemail which led to the romance! We love a direct man!

After almost two years of dating, the new couple attend their first Golden Globes red carpet together on January, 23 1993 in Beverly Hills.

March 1996 — Sarah Jessica Parker and Matthew Broderick Work Together For the First Time

The two take their chemistry to the stage! After dating for five years, they decided to work together on Broadway for a play, How to Succeed in Business Without Really Trying. This was their debut of working together and it was so sweet!

May 1997 — Sarah Jessica Parker and Matthew Broderick Tie the Knot

The two finally get married after years of dating! They ended up doing a surprise ceremony for all of their closest friends and family to enjoy while SJP's sister officiated the ceremony. Sarah Jessica Parker didn't even wear white on her wedding day — what would Carrie think?

She later told Marie Claire in an interview, "I wore black on my wedding day, and I really regret that," Sarah Jessica Parker says. "I was too embarrassed to get married in white, and both Matthew and I were reluctant to have people pay so much attention to us. Which is ridiculous, because that's when you can relish the attention, when it's natural. We treated it like it was a big party on a Monday night, and I regret it."

But it definitely wasn't bad luck to not wear white because the couple is now revered for having one of the longest lasting marriages in Hollywood!

August 2002 — Sarah Jessica Parker and Matthew Broderick Are Expecting Their First Child

Sarah Jessica Parker was pregnant with her first son during filming for the fifth season of Sex and The City (although the wardrobe department did a great job at concealing the pregnancy for Parker's on-screen character). The couple remained very private throughout their whole pregnancy and birth.

September 2004 — Sarah Jessica Parker Wins Her First Emmy Awards

Sarah Jessica Parker won an Emmy Award for her role in our favorite show, Sex and the City. She thanked her three cast members in her speech and then went on to thank her family, including Matthew, who was of course sitting in the audience proudly watching her experience this incredible moment.

November 2006 — Sarah Jessica Parker And Matthew Broderick Are All Family

As it turns out, talent runs in the family as Matthew's mother, Patricia Broderick, was a well-known artist and playwright. Here they are pictured at an art show in New York that was honoring the late artist who had passed away a few years before this. Keeping family close is clearly important to the couple, as they remain a tight-knit family unit even now.

June 2009 — Sarah Jessica Parker and Matthew Broderick Have Twins

In 2009, the couple welcomed twins! Holy moly! The former group of three became five with the birth of their sweet twin babies. The twins are now in high school, believe it or not! Broderick said of the twins being super close on Live with Kelly and Mark, "When it was time to decide for real," Matthew explained, "they were like, 'No, we're going to the same high school.'"

March 2010 — Sarah Jessica Parker and Matthew Broderick Attend The Oscars

The pair showed up to stun at the 82nd Oscars together. They looked fabulous, in no surprise to anyone. In this photo, the pair had been together for around 17 years.

September 2011 — Sarah Jessica Parker Talks Parenthood

Fast forward to 2011 where their oldest is a toddler and the twins are still very young. We can't imagine the busy-ness for SJP and Broderick, balancing life and work while having three young kids under the age of five! SJP told E! that "Everyone should be scared of motherhood." She goes on to elaborate that, "It's good to be scared. You should be! Love is scary and friendship is scary and children, even more so." Well that we can definitely agree with!

June 2016 — Sarah Jessica Parker And Matthew Broderick On "Conscious Coupling"

The couple ditched their shared home and instead opted for two adjoining yet separate townhouses to create a better space for "conscious coupling" which allows them to work harder on their marriage and commitment to each other. They made the move as an effort to allow some individuality but still be a united front when it comes to their commitment to their marriage and staying together.

February 2020 — Sarah Jessica Parker and Matthew Broderick Star on Broadway Together

The showbiz stars paired up once more to do a show on Broadway in 2020! They reunited on stage together in Neil Simon's Plaza Suite play. SJP said of the experience in an article to the Hollywood Reporter, "I think we were more so thinking about the play, like, “How are we going to do this?” And I only thought about being concerned when people ask us, “Are you concerned that this is going to be harmful to your marriage?” And then I was worried. “Well, should we be?” We’ve never spent this much time together ever, even before we had kids." She later went on to say that despite it being strange to navigate that it was still a great experience to spend time together working!

December 2021 — Sarah Jessica Parker Premiers And Just Like That

And Just Like That, the show is back! SJP showed up in a stunning outfit with her sweet son and husband to support the return of her iconic show. She walked the carpet to celebrate her work with the two men in her life. It was a family affair!

Current Day — Still As In Love As Ever

While on Howard Stern's show recently, Sarah Jessica mentioned that her and Matthew Broderick haven't been apart since they met over 30 years ago. She said they have, "never spent a night apart since then, with the exception of work on location, or his mother was ill for a bit so he went to take care of her, but from that first night, we’ve never been apart.”

What else does she have to say about him after all these years? "It seems so silly, but I think you're very lucky if you like the person," she told People. "I still just really like him. I'm sure I annoy him and he annoys me, but I literally learn about him every day. I'm like, 'You're doing what? You're reading what?'

"I think marriage has a lot of vitality," she added. "If you're fortunate, it's like this dazzling organism."

We couldn't have said it better ourselves, SJP! This is a marriage that we are definitely still rooting for after all these years!

This techy card game prompts you and your friends to compete in smartphone-based tasks. With assignments ranging from “Find your best #selfie” to “Create an emoji masterpiece,” you’re guaranteed belly laughs and conversation starters galore. Just like with Cards Against Humanity, each round has a judge that picks the winner, so get your phone stacked with game changers now.

If you want to spark real conversations with your guests, this is the game for you. By the end of this game, you’ll be surrounded by plenty of new pals. Play by drawing a card and answering the prompt to get to know friends and strangers alike on a deeper level.

This is the perfect game for anyone who has spent way too much time on the internet. Match funny captions with well-known internet memes (a rotating judge picks the best one) to create an afternoon or evening of hilarity.

Gather your closest BFFs and spend the night with some good ol’ trash talking (therapeutically, of course). You’ll definitely find out who had the craziest ex. Gather friends that are down for the drama and start by pulling a card. Some of the topics you’ll fill-in-the-blank include: 1. The biggest red flag. 2. What is your ex up to now? 3. The worst rebound.

Grab your girlfriends and stir the pot with this hilarious card game. To play, whoever has the most Instagram followers goes first and rolls the die. “Whichever side of the die lands face-up, take the top card from the corresponding color deck. Read it aloud to the group & perform whatever action is on the card,” the instructions read. “Some cards involve just that player, some require the whole group. The player to their left then rolls the die & the game continues like this. Every winning card gets you a point. 1 Card = 1 Point. The player with the most cards at the end wins!”

If you’re looking to reeeally get to know your friends, this is the game for you and your group (um, and maybe an invite to the new person you’ve been dating is in order). By reading questions and providing answers, you’ll quickly and creatively get inside the mind of all your party guests fast.

You’ll really get to know the other party guests with this game. This might not be one to play with your new coworkers or mother-in-law!

To play, each player will draw six cards. “When it's your turn, choose one of your six question cards, then ask it to the player you think is most likely to answer YES. If they say YES, you get to discard your card. If they say NO you have to keep the card and try to use it again later,” the instructions read. With Skip Cards, Draw +1, Draw +2, and ALL PLAY cards, there's a surprising amount of strategy. The player who discards all of their cards first becomes the winner.

This provocative game will leave your jaw on the floor from the hilarious, creative and outrageous things your friends say. Simply by drawing topic cards like “Things a chimp thinks about when he sees you at the zoo,” responses are sure to be out of this world. After everyone writes down a response, and the best part starts — you all guess who said what. Let the finger pointing begin.

Who knows each other best? This card game will (literally) put everyone’s cards on the table.

Getting started and playing this card game is super simple. A rotating judge asks the group a question about themselves from each of the three levels (indicated on the chosen card). Then, everyone chooses their answer. If you guess the judge's answer correctly, you get a point. The player with the most points wins.

Are you basically Michael Scott from The Office? Any sucker for jokes and innuendos will love this saucy game.

This one is fun to do with the kids or you can spice it up with an adults-only game. Like speed scrabble, the game comes in a convenient banana-shaped pouch making it great to play on the go.

Get ready to laugh the night away with this far too funny game. Each group member will take turns reading the cards’ prompts. With each prompt, every player will answer “yes” or “no.”

It’s part Cards Against Humanity, part Pictionary. If you have friends who are particularly good artists (or even if they’re not), this game will bring you hours of fun.

Created by comedian Jeff Foxworthy, this game is based around familial interactions gone wrong with a Cards Against Humanity style of playing.

If you follow the popular Instagram account, then you can probably guess the basics of this board game. Go places, gain followers and get famous to win this pop culture game.