>> byron: tonight, 25 years of "sex and the city." the ground-breaking show that's still giving voice to generations of women. >> if it wasn't a shared experience that was real, it could not be made up.

>> hello, lover. >> byron: shoes, sex, and sisterhood. four women in the big city changing the way we worked and dreamed, lived and loved. >> oh, berger broke up with me on a post-it. yep, read and it weep. >> byron: diane sawyer asks sarah jessica worker all the important questions. >> did you feel you were a samantha or miranda, or did you feel you were all of them? >> byron: and they're back. >> carrie, party of three? >> that's us. >> byron: reuniting with old friends and making new ones. >> it was always very white. and that was something that was never -- never, never really sat well with any of us. >> byron: older and wiser with a message for women in their 50s. >> why should we be hiding? to lock everybody over 50 up? >> byron: this special edition of "nightline," "couldn't help but wonder: 25 years of sex and the city" will be right back.

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♪ ♪ >> byron: good evening. thank you for joining us. it's friday night, and single women across america are gearing up or wrapping up a night in the city. 25 years ago, carrie, charlotte, samantha, and miranda revolutionized television. showing us how to live, love, and play. tonight, diane sawyer talks to

sarah jessica parker about the legacy of "sex and the city." >> reporter: "sex and the city." 25 years ago, it was not just a tv show, it was an earthquake, a daring roadmap for single women about being brave, messy choices, living with your mistakes. and who would dream that the philosopher queen of being single would be the girl in the tutu? and now here she comes in those eye-popping shoes, walking down the street. 5'3" of power and a big laugh. when the show started, they blasted the rules about conservative clothes, saying women should wear what they want. clothes that say be yourself and go for it. >> in terms of carrie, there were no rules. you wear what you like. you try to tell somebody who you are the minute you walk out the door.

>> did the clothes drive you crazy at some point? >> the fittings were often very long. five hours plus. >> whoa. >> and it was tiring sometimes. and i was poked and pinched and zipped. but they were hugely joyous. >> did you ever make a mistake? >> lots of mistakes. >> if you could delete one? >> i sort of enjoyed the things that people reacted strongly to. and it never seemed to matter to her what people thought. what line is quoted most to me on the street from "sex and the city"? i'm going to say -- but i will be probably wrong -- is probably, "hello, lover." >> reporter: those shoes. the ones that promise dreams you can't afford but buy anyway. it's hard not to see the shoes rooted in the dreams of a little girl named sarah jessica parker, who grew up on the financial

edge. in a family of eight children, little money on welfare, sometimes skipping christmas, lucky to get a 99 cent dress or a new pair of shoes. but that tiny girl would play a big role in supporting her family from the time she was 8 years old. because she had a big gift, and here she is, the lead in the musical that needs no introduction, "annie." ♪ tomorrow tomorrow i love ya tomorrow ♪ ♪ you're always a day away ♪ >> what's your favorite thing in the whole world? >> rainbows. i like rainbows a lot. and i like new york city. >> reporter: and the memory of life on the financial edge doesn't go away. even though now, think of shoes, and she owns the store.

>> hello! >> hello, oh my goodness, it's beautiful. the fear that it will all vanish somehow? >> i think the fear that i won't have money always exists for me. i always think, i have to be earning money. >> reporter: and who knew a tv show with dating, sea vcrets, sex, would e on for generations did? just ask your daughter, granddaughter. >> i'm a samantha. >> i'm a try-sexual, i'll try anything once. >> i'll try anything once. >> i'm a carrie with a dash of samantha. >> i'm samantha. something wild. >> i think carrie is helping me be -- you know, understand that i don't have to be perfect to be the main character in my life.

>> i think, like most women, i'm a combination of all four. >> reporter: she says the conversations about sex when you're single -- good sex, bad sex -- were always based on true women and what really happens. >> there's a rule in the writers room on our show, has been from the beginning, that if an experience didn't happen to one of the writers, if it wasn't a shared experience that was real, it could not be made up. and always saying it is taming it. >> finding a place alone, you don't need a man. >> i don't. >> everyone needs a man. >> it's biological destiny. >> hello, do you want to be saying that? >> your relationship is my greatest fear realized. >> excuse me? i don't believe this. >> did you feel you were a samantha or a miranda? or did you feel you were all of them? >> i think -- gosh. you'd think i would be able to answer this question by now. i think i'm probably a mix of

miranda and charlotte and carrie. i think samantha always had a sort of courage that i don't think i could muster or summon. >> reporter: so 25 years after "sex and the city" arrived, what questions are the now 50-year-olds and their new friends exploring about life, careers, sex? and what really makes you happy? what's the biggest question in your 50s? >> for carrie, it was, you know, a momentous event that changed the course of her life and how to be single again. >> what do i do now? >> oh, honey. oh, honey. >> reporter: and maybe, when you're in your 50s, it's time to take a look at the biggest mystery in everyone's life. the most exciting, challenging, significant relationship of all is the one you have with yourself. >> yourself, yes. my father just passed. and my mother, she's alone for the first time in her entire life.

and you cannot be prepared. loss is unique. grief is unique. loneliness is unique. independence is unique. >> reporter: another treasure hunt in the new season, favorite faces coming back. kim cattrall is coming back for a scene. >> she is. >> you're executive producer, you were part of the decision-making on that? >> yes, definitely. i think a really nice idea to celebrate our 25th anniversary, to have this surprise appearance. we're all disappointed that it leaked. i mean, i feared it would. because it's kind of -- it was like a kernel on hot oil, you know. it's like we forgot to turn the flame off or something. at least the content of it is still, thus far, a secret. >> reporter: even some of carrie's quirky old clothes will make subtle reappearances in the new season, reminding us that

live is the tapestry you weave out of when you were a triumph and when you fell on your face. >> maybe our mistakes are what make our fate. without them, what would shape our lives? >> your life is in some ways more interesting on the scaffolding of your mistakes? >> i think so. do you think so? >> i think so. fortunately, i have a huge scaffolding. >> you don't will be i'd be happy to see if i could do this many. i think success is -- feels better, right? but the things that were painful, the things that were disappointing, the things that i did wrong, i always say it's like scar tissue. >> the world would be a lot less funny without the stories we tell about our mistakes. i mean, really. nobody wants to hear the story of your grand success. well, i guess i just did want to hear yours. >> reporter: a 58-year-old woman wondering, like all of us, what the next question will be? will there be sex in the city in your 70s?

are you golden girls? >> do you know how young the golden girls were? >> yes, amazingly. >> younger than i am right now. ♪ travel down the road and back again ♪ >> yet they were living in a retirement community. which i haven't really considered yet. i think we could, i think anybody could. i think anybody can do whatever they want. >> byron: our thanks to diane. coming up, and just like that, the ground-breaking show returns with some old and new friends. my a1c was up here; now, it's down with rybelsus®. his a1c? it's down with rybelsus®. my doctor told me rybelsus® lowered a1c better than a leading branded pill and that people taking rybelsus® lost more weight. i got to my a1c goal and lost some weight too. rybelsus® isn't for people with type 1 diabetes.

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>> byron: just like that, it's been 25 years since "sex and the city" became appointment television. now they're back again, proving that it gets better later. here's abc's deborah roberts. >> i sense there's a sisterhood here? >> we work hard, but i think we have more fun than people actually are aware of. >> reporter: and just like that, the ladies of "sex and the city" are back more than two decades after the iconic original. the friends, now in their 50s in season two of their new hbo hit. >> and just like that -- i realized, some things are better left in the past. >> now everybody's saying, "and just like that." it's become a whole phrase now. season two. did you expect that would happen? >> no. we hoped. >> it felt right. you know, for us to sort of revisit these characters and examine their lives, be witness

to what was -- what their fe experiences were. >> would you have imagined these lines would be recited by people today? >> and those funny lines. they're very witty, but they capture the moment. right? "he's just not that into you." "i broke up on a post-it." >> on a post-it? >> uh-huh, yep, read it and weep, my friends. >> "i've been dating since i was 15, where is he?" >> they're funny, but they're also real. they're real. >> reporter: from the fashion -- >> swear on chanel. >> i swear. >> reporter: to the friendships -- >> maybe we could be each other's soul mates. >> reporter: and the unfiltered takes on finding love -- >> all the men we sleep with fulfill a certain fantasy. >> or a nightmare. >> reporter: the show sparking a brash new look at modern single women when it premiered in 1998.

it's been 25 years since you stepped in those manolos. >> i couldn't get near a pair of manolos originally. >> really? seriously? >> oh, no. >> i spent $40,000 on shoes and i have no place to live? >> at the beginning of the show, we were mostly creating every character from either century 21 or consignment and thrift shops, bloomingdale's a little bit. our budget was very -- >> modest? >> tender. >> reporter: stealing from one of their famous catch phrases, i couldn't help but wonder, do friendships really last forever? do you feel when you get together, it's just like old times? >> it's real easy. >> yeah. >> you've known each other a long time. >> a long time in years, and a lot of things have happened in our lives, you know what i mean? we've had children, got married, all kinds of things have happened. >> carrie, party of three? >> nice! >> "sex and the city" was all about 30-something women finding

themselves, vibrant lives, vibrant sexual lives. now, and just like that, it's about women who are older. how important is that for you? >> when people were surprised, like oh, you're coming back when you're older. why should we be hiding? why are our lives not interesting anymore? that's insane. and we have to change it. because it's cuckoo to lock everybody over 50 up. >> it's also, story-wise, it's simply no less rich. enormous, important things happen in people's lives after 42. you know? >> reporter: as the ladies evolved, so too has the world around them. the show, more inclusive this time around. >> we love almost everything about our original series, but it was always very white. and that was something that was never -- never sat really well with any of us. and so to be able to go back and change that, and let's keep what's good, let's widen it and

improve it. >> there were a lot of big turns in the last season. your character has left new york city and is headed to california with her girlfriend. do they live happily ever after? or is that too mundane for this sew? >> it's "sex and the city." is anybody except maybe charlotte going to live happily ever after? >> this year we're going to have some charlotte soul searching. >> charlotte may not be as predictable as we thought? >> charlotte often surprises me. >> when we last saw carrie, she was dealing with grief. you have dealt with grief in your own life. >> i think there was an attempt, and hopefully achieved, to have some nobility about the way carrie wanted to experience it and not have it be everybody else's problem. that kind of loss, you sort of make room in your body somewhere in your skeleton. there's, you know, a space for people that are no longer with us. and i think that's what she's tried to do is honor that relationship and look toward what might exist for her in the future. >> that's why it's called "and

just like that." right? you think your life is one way, and just like that, something horrific happens or something tremendously wonderful happens, and your life as you knew it is transformed. >> reporter: season two, a chance for new beginnings and old lovers. >> sitting here with you is like ten years just -- >> you teased us with that trailer, aidan shaw at the very end. tell us about john corbett's return. >> a very happy return. he's comfortable and comforting and familiar. and, you know, ten years have passed. so there's maturity in their relationship. and he has matured in ways that are right and developmentally correct. >> so many people, so many fans on social media, were so excited to hear that samantha will make an appearance. >> it's the 25th anniversary of the show. it felt like something really nice and happy and a nod to this experience that all four of us shared. >> sweetheart, this is the first

time in the history of manhattan that women have had as much power and money as men, plus the luxury of treating men like sex objects. >> it's a cameo, very small. we don't want to oversell it. >> manage your expectations? >> yes, exactly. >> reporter: for many, these ladies broke taboos with their candid conversation -- >> i'm going to write the whole thing off as a bad date with a cash bonus. >> reporter: now, a bit older, they're ready to do it again one brunch at a time. >> i read someplace where you said, this season is about resilience, rebound, and laughter. >> that's what it felt like. it just felt very happy this season. >> byron: our thanks to deborah. coming up, the dress that never made it down the aisle. now back out of the box for one more moment. i have moderate to severe plaque psoriasis. thanks to skyrizi, i'm on my way with clearer skin.

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♪ >> byron: finally tonight, her closet has been a symbol of aspiration for decades. now carry bradshaw is again showing us a timeless outfit is like an old friend, never going out of style. once again, here's abc's deborah roberts. >> vivian westwood. a dress so special, it could bring a wedding tear from even the most unbelieving of women. >> reporter: it's the dress that never made it down the aisle in "sex and the city" the movie.

>> carrie! i freaked out for a minute, but i'm ready now. >> i knew you would do this, i knew it! >> carrie, i'm sorry. >> reporter: the gown revered by some. the headpiece reviled by others. >> i put a bird on my head. >> is that what that was? >> yeah. >> i thought it was feathers. >> there was a bird. >> reporter: during the season premiere of "and just like that" -- >> and just like that, i repurposed my pain. >> reporter: carrie surprising fans with it one more time. >> byron: that's "nightline" for this evening. catch our full episodes on hulu. we'll see you right back here same time monday. thanks for the company, america. have a good and safe weekend.