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Dee Oliver Talks Life, Death, Love & Finding Joy in the Unexpected on The Roundtable!

Well, THIS is a conversation you don't have every day on The Roundtable! And trust us, it's one you don't want to miss! Adrienne takes the host's chair to welcome the fascinating Dee Oliver, funeral director, inspirational speaker, and author of The Undertaker's Wife: A True Story of Love, Loss, and Laughter in the Unlikeliest of Places and Going Out in Style!.. Read More

From the show: The Roundtable with Robert Bannon

35 mins
Nov 6

About

Well, THIS is a conversation you don't have every day on The Roundtable! And trust us, it's one you don't want to miss!

Adrienne takes the host's chair to welcome the fascinating Dee Oliver, funeral director, inspirational speaker, and author of The Undertaker's Wife: A True Story of Love, Loss, and Laughter in the Unlikeliest of Places and Going Out in Style!

Sounds wild, right?! But Dee has a remarkable story to tell!

After marrying into a fourth-generation funeral home family, Dee spent decades helping others navigate life's most difficult moments. But when she unexpectedly lost her own husband, everything changed. Suddenly, the woman who had spent her career helping others through grief had to find her own way forward.

And what a journey it's been!

From unexpected career turns and raising three daughters to discovering the power of faith, resilience, humor, and second chances, Dee shares incredible wisdom about what REALLY matters in life.

It's funny, it's heartfelt, it's inspiring, and it might just change the way you think about living!

Because sometimes the greatest lessons about LIFE come from someone who knows a whole lot about death!

It's another honest, uplifting, and wonderfully unexpected conversation right here on The Roundtable with Robert Bannon!

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Transcript

This transcript was automatically generated and might contain errors.

[0:00] Adrienne: Welcome, Roundtablers. I am here today with the lovely Dee Oliver. Welcome to The Roundtable.

[0:16] Dee Oliver: So happy to have you here. I have to say, just reading through some of the information, what an amazing life that you have led. I can't wait to get into it and hear your take on it. But you are an author, you are a funeral director, motivational speaker. It's wonderful to see all of these beautiful things, and a mother, and a grandma, like so many, so many wonderful, wonderful things. But I would really like to start with how you met your husband, Johnny. If you could tell us that lovely meet-cute story.

[0:48] Dee Oliver: Oh, John Oliver. Yes. We had a date. We had a blind date, which I originally blew him off because I thought he was too old and all of those things. And then we had a second date. And with that, he said, you know, we'll go to dinner. I said, great. He picks me up. He's got this fabulous sports car. And I knew of funeral directors, but really when you're going through life, unless you actually are related to one or have personal experience or friends of a family that is one, you really don't know a whole lot about funeral directors. And so he picked me up. And as we're driving down the road, he says to me, he goes, well, I'm on call tonight. And I said, well, that's great. And he goes, so I might get a call and basically have to pivot the evening.

And I said, that's no problem. And I'm thinking, you know, I'm a whopping, at the time, I think I was like 20, 21, 22. All I can think of is this is a good meal, you know, not him, but going out to dinner. And with that, sure enough, his pager goes off. We pull into 7-Eleven because that was before cell phones and use a pay phone back. And he says, I need to go to the office. This won't take long. Do you mind just kind of rolling with this? And I said, no, it's fine. We go back to the office. At that time, I didn't quite understand that he was actually living in the funeral home. So he says, I'll be right back. I sat in the car. He comes back down. Navy blue blazer khakis are gone. Loafers are gone.

And we've got a black pinstripe suit on and his tie. And he just escorts me out of the car into what I now know is the removal wagon. And we get into it. He takes me into a part of the city, which I knew fairly well, somewhere I didn't know. We pull into the driveway and there are two other men dressed exactly like him standing there waiting for him. And he goes, he just looks at me and he goes, I'll be right back. This won't take long. So I said, great. Now I was still smoking cigarettes at the time. And I let one up and roll the window down and I'm happy as I can be. And the next thing I know, I hear the back door open. So remember, it's a station wagon. So the door swings sideways. And the next thing I know, I am lurched forward and right next to me is a cot with a white sheet on it.

And he gets in and he's cute as a button. I mean, blonde hair, big brown eyes, the whole thing tan. And he looks at me and he goes, okay, we're all done. We're just going to go back and we'll get things situated. And I looked at him, I said, who is this? And he goes, oh, that's Mrs. Smith. Don't worry about her. And I went, is she coming to dinner with us? He goes, no, no, no, no. And we immediately take Mrs. Smith back to the office and he changes his clothes and then we get into his regular car and off we go to dinner.

[4:23] Adrienne: Wow. Oh my gosh. That is amazing and wonderful. And is that kind of what made you write The Undertaker's Wife? That was your first book, right?

[4:31] Dee Oliver: No, actually Going Out in Style was my first book. I wrote that after Johnny died and I realized that here were two funeral directors, him being fourth generation, his funeral home's been in business since 1865, since the Civil War ended. Amazing. That's when all basically funeral homes or funeral parlors at that time, they were called, actually established themselves, was after that war. And I realized that we had completely did everything wrong and nothing in what we advise our clients or our friends out in the world. We had nothing done. It was a complete catastrophe when he died. And I went, how on earth did we not do what we know to do? And so I started researching books about grieving and planning for funerals and they were all really morbid and just really not very, not that they weren't well written, but not enough to captivate somebody to want to read it.

And so I said, all right. And I started blogging about all the things that we did wrong as professionals in the business. And now I know why we tell you all to do the right things. And so basically it pokes fun at me not having our act together.

[6:11] Adrienne: Right. Now, if you can share with us as well, it must've been shocking when it happened, but when he did pass away, I mean, I can't even imagine. And I married late in life. I met my husband actually in 2020, January 3rd of 2020, right before the world shut down. And I never thought I was going to get married. And I was in my mid-forties and my mother always said, you're going to find your person. Every pot has a lid. That was what she would always say, my grandparents too. And I just can't even fathom that happening. And if you could talk a little bit about how that changed you.

[6:46] Dee Oliver: It's interesting when you do this for a living and you understand how frequent death is. Most people just, they have a handful of people that they know that die, friends, grandparents, a parent, a cousin, things like that. But when you have a business and that's what your clientele is, you realize how frequent death is. I guess it's like being an obstetrician. You realize how many babies are actually born. Other than that, the rest of the world just thinks five people die in their life and everybody else stays put. And so I knew that it would eventually happen, but I just didn't expect it quite that as young as we were. So it really changed. This is a hard question for me because we always appreciated life because we saw death.

And so we knew the value of every day that came and tried to really appreciate it. But the world gets in the way and we're all human and it sounds good on paper, but I think it gave me a better perspective of how deep a loss is and how big of a void it can be for people and then really understanding how to fill that void for other people. I don't know if that makes sense.

[8:41] Adrienne: It does. And I will say, when Robert had mentioned I'd be interviewing you today, I was like, oh, this is very interesting, coming at an interesting time. Five years ago, we lost a family member, a cousin, we lost a cousin, and her name was Julie. And it was extremely shocking and unexpected. We don't know exactly how or why it had happened and it broke all of us. It was just, we couldn't believe it. And I still to this day, I said to my mom the other day, I say, it feels like it was yesterday. And we were such a close family and everything. And when it happened, because when my mom called me, I said, I thought it was her husband, Michael, because he had been sick. And I'm like, what? And she said, no, it's Julie.

And I'm like, is this a joke? It was just so shocking. And I drove there and I went in and she had passed in her sleep and she looked like she was sleeping. And I went over to her, I had to touch her, because I'm like, this has to be, this can't be real. And she was cold. And I talked to her for a few minutes and I was like, how are we going to get through this? And it's been so tough.

[9:55] Dee Oliver: It is. And grief, and I've lost many people of all different ages in my life. And grief is hard. And grief hits people differently. And I feel for her daughter, because she was an only child and she was so close to her. And it still affects her. Like I said, it seems like it was yesterday, but she was just my cousin. She was somebody's mom. And she was a grandma, too. She was a Mimi. We all called her Mimi. You also are a motivational speaker. What do you say to people when you see them in that manner after going through what you had went through? Any advice that you can give to those out there that may be going through it and still going through it?

[10:39] Dee Oliver: Well, grief is a really interesting emotion. I mean, you can read about it. And until you, like you, experience it, it doesn't ever go away. I mean, I've been married to Boyd now for 11 years. And Lord has blessed me incredibly so. But Johnny's always there. When you love somebody, which is such a gift to have that emotion and to have that privilege to love and treasure another human being, when you lose that person, that's sort of the price you pay for loving the person. But the grief, I think always, it definitely always stays with you.

[11:32] Dee Oliver: Just changes. It changes so that you can find humor in it again, super fond memories of that person. It also, you know, it's funny, somebody asked me about the girls the other day, and I said, you know, they were young when he unexpectedly died. I said, my mother was an airline stewardess, and she said, you know, everything happens in threes, according to the same. Yes, we believe that as well. And so my dog, Johnny and I had to put the dog down, then Johnny died, then my mom died 45 days later. And I'm standing there looking at the sky going, you know, God, you know, I have this great faith with you. But really, maybe I could have come up with a better plan than this. I mean, talk about your core family, the dog, your husband, and then your mom, like that.

And yeah, I know. It's like, hey, can you give me a little break? Like what's going on? Yeah. But looking back, because hindsight is always such a wonderful thing. I look at the three girls that we were blessed with, and they were 9, 10, and maybe almost 12. And Madison said to me after Johnny died, and truly, it was so unexpected. She said, so now what? Wow. You know, she was, what's going to happen? And I went, nothing's going to happen. I mean, everybody has a date of birth, and everybody has a date of death. And this was Dad's, and he had lived his life completely, according to God's plan. I said, you are going to go on and have the most wonderful life, the life that your daddy and I always dreamed you and your sisters were going to have.

You're going to grow up, you're going to go to school, you're going to go to college, you're going to get a great job, you're going to marry Prince Charming. All these wonderful things that we dreamed about are going to happen for you. And that's not going to change just because Daddy's not here. Of course, I walked out in the hallway and went, oh. You know, you don't want to rattle the world too much. And I will say, those three girls, I don't think they saw so much over the years and watched me navigate this road, that they have the strength and this character and this empathy that I could have never taught. They are better women than I could have ever raised because of just the experience and what they saw and how they realized that life is just so fragile. I don't think I would change that just because of who they are, if that makes sense.

[14:45] Dee Oliver: The grief is just a really... In my book, I write, you go through the first year and you're like, okay, you get all the milestones, birthdays, anniversaries, Thanksgiving, Christmas, Father's Day, Mother's Day, Easter, all of those things that you celebrate. And everybody is like right there with you. They're walking you through, they're remembering. Second year comes and this is all human nature. Everybody thinks, okay, she's good to go, right? That second year comes, it's worse than the first year. It just is because all of a sudden everybody's busy and they're doing things and they have gotten you through that terrible year. But now the second year comes and you're just kind of standing there going, oh, this is really not at all what I expected.

And that year I think is probably the hardest. And so I always try to advise people, don't forget that person. Right. Don't forget that person when you're having a dinner party. I know it's an odd number when you have to do seven or 11 or nine or whatever it is, but to tuck in a chair at the table and have them, that's going to be the biggest gift you can give that person. Right, right. You know, those are the kind of things that we always had. I always sent flowers late, not in the beginning, like three months to six months later, just kind of, hey, thinking about you. Right. Because initially it's everybody's there, everybody's over. And it's true. It's after that. It's like those next couple of months, the first anniversary, you know, the birthdays, the holidays and things like that, where you're just like, you're kind of sitting there and you're like, oh, so this is how it's going to be.

And it's true. It really is. And we do try. And I think it's so important to talk about them, like to share those wonderful and we have so many wonderful memories, you know, of those times. And, you know, there are those little, I see those little signs every so often and whatnot. And it's like, OK, you know, you know, I'm thinking about you or whatever that may be. And it just it gives me a sense of calm when that does happen, no matter who I may be thinking about. And I'll see something and I'll be like, OK, grandma, there you are. Or if I'm going through a tough time and I'll see something and I'll be like, oh, my gosh, like that, just that one little moment, as small as it may be, gives me a little more like, OK, you're here. I got to get my stuff. You know, I can do this. I can get through this. And it's weird. I know people believe different things, but I do believe in those little signs. I really do.

[17:38] Dee Oliver: Oh, I totally do. And I think you when Johnny first the first couple of years, his birthday, instead of ignoring the birthday, because it's not like the girls don't know it's their father's birthday. I'd get a birthday cake and we would have a birthday dinner and we would have a cake and we would sing happy birthday. As crazy as it sounds, it just acknowledged that he just because he wasn't here, like you said, they're not to be forgotten. They love the stories of their daddies. They love when any of the funeral directors tell some funny story about their dad or a friend goes, oh, my gosh, you know, I remember this and I remember that it because as time goes by because of their age, they have those memories start to fade a little bit.

And so they like the reminders of that in the photos of him. And that's one of the things I said in the going out in style book was don't do anything for the first year. Right. Unless you absolutely financially have to change what's happened to you. If that's driven that way, then that's a different reason. Right. But the rest of it, just leave it alone. Yeah. Everybody wants to be fix it for you. Right. And you can't fix it. You actually have to go through that time of grief and the highs and the lows. And and I so I always said, don't do anything for a year. Don't move the sunglasses. Johnny's sunglasses. I think I think they didn't move actually until I think I got engaged to board. I think it was like seven years later.

His sunglasses were still where he left them. But I left his suit hanging his suit coat hanging on the closet door and his dresser was filled. I didn't need a space. I already had my space. I don't need to empty his clothes. I mean, that's where they belong. But what I saw over the years was that the girls would open it and they would go through it and they would touch it. And they and it gave them and even if you don't have children living with you, it still gives you comfort. Yes. You know, it's that familiarity of that loved one. And then, you know, it makes you cry and all those things. But you it's a process. You kind of have to get through it.

[20:19] Dee Oliver: Right. It's true. It's true. And I so appreciate that. And now you're celebrating 10 years of the Undertaker's wife. I mean, what an accomplishment. My goodness. Thank you. Thank you. So what is next for you? Gosh, I'd love to do a sequel to the Undertaker's wife and eventually and then continue with speaking and just really sort of informing people about funeral homes, how they function, how they work, why they do what they do and why you need them. How to process things, wills, and I always call them pink job, blue jobs, sharing information, you know, because one of the things and I still have his key chains. He died and I've got Johnny's key chains and he keys to everything. And I'm like, I have no. I mean, do you know what's on your husband's key chains?

Do you know where those keys go? It's so interesting that you say that because I'm like, I there are things that I don't know that you don't think you don't know. And just as a side note as well, my brother in law is he's going through breast cancer right now. He's doing very well. He's 69 years old, just came upon us this this past April and we're going through everything. But he didn't have a will, you know, and he's like, I don't have anything. And I said, but you do. You know, yes, you are disabled and you have those things. I'm like, but you have physical things. And it's true. And it's like, I'm young. I didn't I didn't think to do that. And just going through that process, process, we learned so many things.

And I'm like, wow, like, yes, people don't know. People don't realize. And people aren't prepared either because they think, oh, well, I'll do it later. No, it's it's classic. It's it's classic. Everybody thinks everybody else is going to die except them.

[22:18] Dee Oliver: It's true. That's how that works. And and I think it's just so that we don't wake up in a panic every day. Like, is this it? But like, you know, your brother in law, Johnny and I, our will was out of date. It didn't include our third child. Oh, my goodness. And it just it went on and on. We'd never we had we owned an entire cemetery of 40 acres. We had cemetery property in every cemetery in the city of Virginia Beach and Norfolk. Never once did we have a conversation of where should we be buried? I ran the stone company that made the headstones. Did we ever discuss the kind of headstone we wanted? No. I mean, it.

[23:04] Dee Oliver: That's why I say it's just so interesting that people, I kind of joke, I said, people will research a television more than they will pay attention to a funeral home. And then they get in there and then they decide, I don't want to be here, I don't like this. And what I always said is you can leave a funeral home. I mean, even if you're on, Agnes is in the back and she can't leave when the funeral's happening. But up until that time, funeral homes are, most of them are family owned and they don't want you not to be happy. So you can actually leave the funeral home. You can say, you know what, I'm going to go home. I need to talk to my family. Thank you for picking up my aunt. I know she's in the back.

I'll get back to you. And you can drive to the funeral home down the street and you can say, I just don't really like, I'm not comfortable there. I'm just not resonating with them. Can you help me? And they'll say, no problem. And they'll call the funeral home. They'll go get your aunt. They'll settle up the bill and you can use them. Wow. And the other funeral home's like, great, because we don't want anybody not happy. Right. I think that's, and you know, people, I don't think people realize that. And, you know, I did watch the TV show, Six Feet Under, my dad and I, we, you know, we really enjoyed that show. But in watching that, I was like, wow, like I didn't know, you know, everything that was entailing of owning one and going through all those different things.

And it really was interesting. And it's just like it, and we had a family member who passed away and we went to Montreal, Canada. They did things so differently than here. And we were all looking at each other. I mean, we grew up in Italian, you know, typical New Jersey, East Coast. So, you know, three days, all the, you know, all that stuff. And it's like, and here I'm like, what is happening? Like, it was so different. And we're like, but we, we were like, it was wonderful. Like everything took place within this beautiful funeral home. They had like a cappuccino area. I was like, and so my sister's like, are we allowed to do this? And they're like, oh yes, please help yourself. And we're like, and, you know, I turned to her and I said, everyone's grieving.

You don't have to, like, if you want something to eat or you want, it's here and they have a beautiful room set up where no one has to drive, you know, it's all right here. I'm like, this is fantastic. Like, why don't we do this in the US? Like, it was just a wonderful thing. And, and, you know, my sister's looking at me like I had three heads and I said, people are going through the worst moment in their lives. Isn't it just nice that, you know, everything is right here, you know, like for us, it's like, well, where, what, what Italian restaurants doing the repass after the burial, like all those, you know, different things. And it's, it's very interesting to me, but I, I, I love that you said the funeral home wants you to be happy. And that is, that is, that is true. That is very true.

[26:09] Dee Oliver: Because they know, I mean, we know you're having the worst day of your entire life. And we also know that the family is at odds. People are starting to argue, things aren't going down well. And we're just trying to make the worst case scenario, the best experience that you can have to honor the person that you love very, very much. And, and so, you know, when you were talking about your, your brother-in-law, you know, I don't have anything. Well, what's interesting is, and I do this with my girls, like we'll go through the house and I need to actually write it down. So, you know, here we go again. I think I've learned the first time around. What, what do you want? You know, do, do you want the Turvis tumblers with my name on them?

You know, because those are the things that people end up fighting over. It's not the big diamond engagement ring or the, the family silver. It's those chipped juice glasses that everybody drank out of before they went to school all of their lives. Those are the ones that'll get two people rolling around on the floor, tussling and fighting, you know, because that's, those are the, those are the sentimental memories. And so, as, as the senior person in the family, the best thing you can do, I know that's what made, and so that's what makes me really sad is that you watch families walk out of a service and you know that they will never speak to each other again. And it's always because either the parents put them at odds or they just didn't tidy things up.

And, you know, my goal was to make sure that when Johnny and I passed away, that my girls would have each other in the world, that they had the people that, that they love and depend on. And money will bring people at odds so fast. And so the best thing you can do is walk them through the house and go, okay, you know, who wants this book? You know, and you write it down and you write it down and everybody's in agreement. And then you have a will that's, you know, current, not like my old will. And of course it didn't matter because, you know.

[28:49] Adrienne: Oh my goodness. This, Dee, thank you so much. This was so eye-opening, so wonderful. And, and something that, that I, I did need, but, but before I let you go, so what, what is next for you? What are the next things that you're going to be doing that we can look out for?

[29:02] Dee Oliver: I hope that I'm going to be on a couple of talk shows and do some speaking engagements. And so, you know, we'll just see what, we'll just see what the future brings, but it has been such, such a pleasure to be with you today. Thank you so much for, you know, spending time with me.

[29:21] Adrienne: Thank you for coming. This, this, and, you know, initially I was like, oh, and, and when I, like I said, when I was reading through everything, I said, oh my goodness, like I could feel a connection. Like I definitely, and it's funny when you were talking about birthdays, I want to talk about that too. After my grandmother had passed, now she passed, she turned 90. My mom didn't, and she was, she was in a nursing home at the time, which she had wanted, and she didn't want to party. Then all of a sudden, like literally a week before, she goes, oh, isn't everybody coming? And my mom's like, I didn't do anything. So in a week we scrambled, got something together, and it was, she had celebrated it on Wednesday.

We were there on a Saturday and we're getting all together and, you know, she's going to have lunch. And at the time she was very frail in a wheelchair and we were bringing stuff from her room because they have a, um, like a, a room you can use, you know, for, for celebrations as such. And all these things, and my mom did picture boards, like she went all out for her, right? We had a cannoli cake, like she was all excited, and we have all this stuff. And she really couldn't see very well at the time. She had her lunch and I, I mean, I said, hello, I saw her, I saw her, her roommate, you know, she was at, didn't really have a chance to talk to her. And, you know, we, we do everything, we, she sees everything in the room.

And then my mom said, all right, mom, I'm going to put this hat on you. And she didn't like wearing hats. And she's like, all right, fine. She goes to put it on her and she's in the wheelchair. My mom's just about to take a picture. And she goes, ooh, my grandma that makes this sound. And my mom goes over to her, hugs her, and she falls into her. And my mom, so there was a gentleman in the room, his father was by the window. He goes, I think she needs oxygen. And my mom ever so calmly goes, honey, go get the nurse. And I'm like, what do you mean? What's, what's happening? And she goes, just go get the nurse. And I knew I could tell. And so the gentleman starts fanning my grandmother. I turned into Shirley McClain and went out there and was like, my grandma needs oxygen.

And they're like, Adele just had lunch. I'm like, you don't understand. And they came in and the doctor's like, she's fine. And my mother goes, she's gone. And she's like, no, she's, I feel a pulse. My mom's like, nope. And she did, she passed away. And it was the craziest thing. She didn't want a funeral. She didn't want any of that. And here we are in this beautiful room decorated with food and all of her favorite things. And I'm like, did this just happen? Like, oh my gosh. And it did. So we kind of had, and then people started pulling up. We saw them with flowers and balloons. And I'm like, oh my gosh, what am I going to do? And my mom's like, okay, go to the door. So people come in, and I'm like, so like 10 minutes ago, and I laugh about it now, but my mom said, we will never forget that.

And my mom was always afraid she wouldn't be with her. Like when it happened, how great is that? And I said, we have this amazing story that we can tell. And it's like, so all, and of course everyone's like coming in and there's like a line. And my, one of my lifelong friends, she goes, did I just hear you? I said, and she was on the couch. We got her Yankee, which is the Yankees fan, her blanket. She was covered up for a little bit. And we kind of had to sequester the people, but my mom had everything. And they came and some people did get to see her. And then they came and took her to the funeral home. She was cremated, but I was like, and my mom's just like, well, what do we do now? And so then I'm like, we have all this food.

So we celebrated her and we sang happy birthday later in the day, handed out cake. We had a huge sheet cake from like, you know, Costco and that's what we did. But, but in that moment, while it devastated me, cause I was so close to her, we remember that and celebrated every year. And we go to her favorite diner. We have a root beer float and a piece of pie for my grandmother. And we do it. I mean, she's been gone about 15 years now. So, you know.

[32:58] Dee Oliver: So did she die on her birthday? It was two days after her birthday.

[33:03] Adrienne: Okay. Yeah. Cause you would be surprised how many people, I mean, and I know this cause, cause I see it, um, how many people actually die on the day they were born. That's not, it's not frequent, but it happens enough that you kind of go, what are the odds of that? Right. You know, amazing. And she was like, she was fine. She didn't have, you know, anything. She was just old, you know, and she, she was frailer and, and it was just so, but my, but she didn't want the party. That was the craziest thing. And then she says to my mom, my mom's like frantically getting everything together. And then, and like I said, I was just bringing stuff from her room and this, that, and the other, and she was having a great having lunch.

And then her poor roommate comes wheeling down the hall. And she goes, can I see her? And I'm like, and I look at the nurse, like, I can't tell this lady, she's going to get all upset. And she goes, oh, I forgot to tell my grandmother's name was Adele. Oh, I forgot to tell Adele something. And I'm like, well, not gonna be like, you know, do that now. It's the craziest thing, but we just, we truly, you know, we, we appreciate it. And, and it's, it's hard, you know, but we, we try to find, and as you do as well to try to find the humor and, and just have them live on in stories and, and tell the next generation of, of those wonderful things. And, and D go, go, go get those books and enjoy and everything. And D such a pleasure to talk to you. I just, I wish you nothing but the best and, and so much success and we'll look for you on those talk shows. Thank you.

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