Real Housewives of New York City fan-favorite Dorinda Medley candidly opens up about dating after divorce, surviving widowhood, and being a single mom—all with a positive attitude and one-liners to boot.

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Dorinda Medley

Real Housewives of New York City fans know one thing to be true: Dorinda Medley is as genuine as it gets. Her fun-loving personality and quotable moments are just a small part of why she's a Bravo favorite; Medley's real life experiences and warm demeanor make the TV personality and entrepreneur ultra relatable.

In this episode of We Are Family, Medley opens up to host—and fellow single mom—Julia Dennison about her close-knit family, becoming a mom, dating after divorce and becoming a widow, and why she's feeling freer than ever right now.

"One of the things that I think is most valuable to me now at 56 that I'm so proud of is my freedom," says Medley, author of the new memoir, Make it Nice. "I have freedom, and as a woman to be able to say that—physically, spiritually, mentally, financially—is such a powerful thing. I loved this experience of writing and exploring that part of myself. And I just literally want to keep entertaining and spreading the love and making it nice and meeting new people and just doing what's good for Dorinda. Not Dorinda Cinkala or Dorinda Lynch or Dorinda Medley or the mom or the wife—just me. I get to be selfish with myself for the first time I think ever in my life and it just feels good. It really does."

Upcoming episodes and topics this season include:

  • Episode 3: Whitney Port
  • Episode 4: Jared Haibon and Ashley Iaconetti
  • Episode 5: Ben Feldman
  • Episode 6: Candace Parker

Listen to We Are Family on Apple Podcasts, Spotify, iHeart, TuneIn, Stitcher, Google, and everywhere podcasts are available.

Listen to Season 2, Episode 2 right now:

Plus, follow along here:

Dorinda Medley: When I think of family, I think of home, safety, love, and freedom.

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Julia: Welcome to We Are Family.

Dorinda: Very excited to be here.

Julia: We're so happy to have you Dorinda.

We're here with Dorinda. She's a TV personality, entrepreneur, entertainer, philanthropist, mother to her daughter, Hannah. You of course all know her as the cast member of six seasons of the Real Housewives of New York City. And she's now the author of her new memoir, Make it Nice.

Dorinda, I'm so happy to have you. Welcome to We Are Family.

Dorinda: Thank you. Well, this hits very close to my heart because as you know, you just read through the book, and a lot of it's about my family and I love, I actually really myself, writing it, enjoyed the beginning, how I talk about I spent my whole life trying to get away from Great Barrington. And here I was in Great Barrington, all these years later, writing my memoir. I had to travel very far to get back home again.

Julia: Yes. And I feel like Blue Stone Manor in Great Barrington is like... It's like a part of the family it feels like or character in your book for sure.

Dorinda: You know what I say about Blue Stone Manor is for me, it's a living breathing thing. It's my home. And I really love it, live with it, use it. It's not a fragile place. I think that's one thing that when people come to Blue Stone Manor every part of it is used. We're in the kitchen. We use the china. There's lots of seating places. There's lots of soft touch things. It's a real home.

Julia: Yes. I love it. And that's what I love about you is you're so relatable in so many ways, at least for myself, but I think plenty of other people, but just to say as myself, obviously I'm a big fan of the show, but I'm also a single mom.

Dorinda: Oh, you're a single mom?

Julia: So yeah, so I'm a single mom and I'm divorced to a British guy who I co-parent with. And I lived in London for 10 years.

Dorinda: Oh my God, you're me!

Julia: (laughs) Yeah, but I was sort of reading in your book that you felt like you spent your formative years there and I was the same. I kind of learned how to be an adult in the U.K. And then I came back to New York for similar reasons because that draw of being close to my family who live over here obviously was too alluring.

Dorinda: Well, I think really the great experience, the great gift of living in London at an early age is that you kind of, it's a really great place to sharpen your skills, right?

Julia: Yes, it's true.

Dorinda: It's a whole different way of life and it teaches you just socially, it's different in how people live and how people interact. And I think I was more of an adult back when I lived in London than I am now. I look at pictures of myself with Hannah and I look like I'm like, I'm playing so adult. And I'm like 26, 27 years old and I had the Chanel jacket and baby and the headband and the nanny and the blah, blah, blah. I really was trying very hard to be like that investment banker's wife in London.

Julia: Right. But I also think there's something about moving abroad that I experienced leaving my family behind and having to create my own friends and family from scratch, which isn't, certainly not easy in any circumstance, but can often feel not that easy when you're in London too, as much as... And now my best friends, the entire world are British. So I got there then.

Dorinda: I have a really funny story. I was living in Eaton Square and my husband was working for Lehman Brothers, Ralph, and he was working 14, 15 hours a day. So literally we landed the next morning. He was like, see ya. He leaves at like 6 in the morning. And I was like, "Oh my God, OK, here we are." And I went across right next door to me and I knocked on the door and I said, "Oh my God, my name's Dorinda Lynch and I just moved there from America. And I just want to meet new friends." The woman looked like I was going to rob her. She was like, "Well, for God sakes, why would I possibly want to?" She was so offended. I thought, oh God, I'm in trouble because you're told that you have to peel the onion over there. You have to be slightly interestingly disinterested.

Julia: Yes. And once you get in there, they're friends for life.

Dorinda: Forever. If I go back there for a week it's as if I never left.

Julia: Same. Absolutely. I think there's positives to having lived so long in another country because you have all these friends, but then you always have people to miss too. But we're here to talk about family and I do think friends are part of the family too. And it's like family you make...

Dorinda: Well I think but you grow up with your family and then you go out in the world and especially if you venture the way we did, you have to create your own family because that's how you're used to living. I grew up in a big ethnic family and there were always people around and food and loud noise, either we were arguing or loving. I am not a person that could not live with other people. So when I moved abroad, it was very important for me or anytime, it's very important for me to have friends around me. Especially strong, I love strong women. And I've always been very lucky because a lot of the women in my life have always been very strong figures. So I tend to strong women. You know what I mean?

Julia: Yes. And what I love is that you start so many of your phrases on the show, but then also in the book with my mother says, as my mother says, and I love that. So she was obviously such a huge influence for you and your upbringing.

Dorinda: I loved being little. I remember being like 14 and my mother saying to me in four years, you're going to go to college. And I had a horrible realization that I was growing up and I bawled my eyes out. I was like, I don't want to grow up because really my house was about my mother. She was the... My father worked tremendously long hours and was always working. And I think I say in the book at one point, I don't know why I loved him, but I loved him because I didn't see him so much. But when he came home, we were always so happy to see dad.

Because he worked 12, 14, 16 hours a day, but everything came from home. We didn't make a lot of outside plans. The goal every day was to get home safe and achieved. You never came home without a story or a success. Guess what I did today? I made... So my mother definitely raised very success-oriented children that, we're always representing the family.

Julia: Makes sense.

Dorinda: We're all very different, my brothers and sisters, but we were very close. We were like each other's best friends. And of course we had the neighborhood friends and stuff, but really the goal was to be home.

And it was filled with love and a lot of food and a lot of discussion, a lot of religion. The first 10 minutes of my life was spent bending and kneeling to different life-size statues in my bedroom. I said to someone the other day, it's no wonder I was ever able to have sex with all those statues around. I was like, all right, St. Anthony, please help me find this. St. Christopher, make sure I have a good trip. Virgin Mary, I love you so much. I'm not going to do anything bad. St. Michael, make sure you will look over me and keep the bad people away. And of course, Jesus, you're just everything. See you Jesus.

Julia: (laughs) So when you moved abroad, so you'd already met Ralph, your first husband, before you moved abroad, right? And you moved abroad together because he was British and I can relate because it was very similar to my situation.

But you said that when you met him, you thought right away that he would make a good father.

Dorinda: I did. I did.

Julia: What about him struck you as being a good potential father?

Dorinda: So I was never a big dater and I'm still not a big dater. It's not good, bad, or otherwise. It's just not who I am and when I met Ralph, he felt, he just was so charming and so kind, and was such a hard worker. And as Ralph says, on our first date, I asked him about his health insurance. He had a very good health insurance. He always talked about that and he just seemed to take a real interest in me. He was incredibly responsible, incredibly kind, ex-rugby player, very good looking, and we just hit it off.

And I was looking for someone that kind of had the same sort of goals in mind as I did and he just seemed to be that guy. And I was right. He's been a wonderful father to my daughter and a very important part of my life. I don't think because you get divorced that you have to get rid of the person.

We just lost touch. It was not one thing. We realized it would be better to keep our relationship intact as friends and be good parents than try to continue on pretending like it was going to be a marriage. And I wanted to have another romantic involvement. I wanted to feel that now that I was a grown woman, I really married Ralph as a child.

Julia: That's how I feel about my ex-husband. This is, so this is blowing my mind. Because there's so many similarities. I'm very good friends with him now. And I really do believe that relationships have expiration dates and it's not to say that it wasn't a wonderful relationship for the length of time it was. But I really take that into co-parenting and I really try to advocate the fact that it's kind of bonkers to me. And maybe you might agree that we expect our partners to be our best friends, our sexual partners, our parents, all these roles and you have to be perfect at all of them. Whereas my ex is a great dad. He's maybe not my husband. He would not be a good husband for me right now, but he's a great dad. You know what I mean?

Dorinda: Well, that's right. And also too, I do think there's something to be said for that. We, it's a lot, Ralph had a lot of pressures, young guy who was working for Lehman Brothers when we moved to London. And I don't think I could fully appreciate that. Who would have ever thought someone like me would have Hannah without any family member around? Like if you told me that as a young girl, that you're going to have a baby one day and your mother's not going to be there in the waiting room. I would've never believed it.

Julia: Yeah. Oh my goodness. The parts in the book, when you talk about your relationship with Hannah just had me balling because I just, it's so wonderful. So touching, but also as a single mom, there's just such a special connection. I'm also a single mom of an only daughter and that sort of special bond and mine's only 5, but it's like looking at your relationship with Hannah. I'm like, oh, this is what it's going to be, it's just so beautiful. Do you think your relationship with Hannah changed when you became a single mom or can you talk also about just that feeling of first becoming her mom?

Dorinda: I remember my mom said, when I was about 6 months pregnant, "Oh boy, finally someone is going to clip Dorinda Lynch's wings. I can't wait." I was like, oh no. No one is going to clip my wings. I have the nanny, the baby nurse, the housekeeper, I'm going to literally have this baby, drop the baby weight. And off to Venice I go in February. Right. I was like, I'm going to be that person.

And I'll never forget the moment when she, I talked about in the book. It really was like, when she came out and she looked at me and I was like, I know you. This is it. This is the beginning, the middle, and the end right in front of me. And I really felt that that invisible string that I felt always from my grandmother to my mother and my mother to me, literally extend to her. And I went home and I was like, I'm never leaving you. You know what I mean? I just... It was just, and it made me grow up so fast and make me so responsible. The thing that really was amazing to me is everything that my mother used to do with her hands and the way she handled it, I saw me doing with my hands and caring for things. So it was just like, I'd been preparing all my life for that role, but I didn't know it. And I had people preparing me for that role. And I didn't know it.

Julia: Right. I related so hard to that because I remember when my daughter was born and I said to my mom like, oh my goodness, my heart is now outside of my body. And I can't fully control it. And that is terrifying. And I said to my mom, does that feeling of that terrifying mix of just extreme love, but then also terrifying because you just can't always protect them. And my mom's like, nope, it doesn't go away. Welcome to my life.

Dorinda: And I also talk in the book too, honestly, that motherhood is hard. It's not...

Julia: Yeah.

Dorinda Medley: There were times where you're like, I don't want to do this anymore. I'm done. There were times when it would be 4 o'clock and dark in London. And I think I really don't want to do this anymore. I'm kind of over it because in order to be a good parent, the monotony is important. They love the ritual. They love the repeat. So, I don't know about you, but there were many nights where she was like, mama, can you please read this again? And I'm like, no, I can't.

Julia: No. Oh my God. So when you're a single mom and you're managing, I always think about like your life as a pie. And when you're managing to try and date and your love life on top of being a mom, it's a big piece of the pie. Can you talk about how you sort of navigated dating?

Dorinda: I've always sort of been a person that dated with purpose, but I definitely dated with purpose once I was a single mom, because I worked as well as a single mom. So I would be up everyday. We'd make our beds, we'd go to, she went to Sacred Heart. I would work. I'd pick her up. She was my focus because I wanted to get her to... I think for mothers, it's not about the micro it's about the macro. You've got a goal in mind to get them to the finish line. You could really screw that up if you don't watch out. It doesn't take much to kind of... We definitely screw up all the time, but got to make sure there's a majority of consistency in your life with them. But I was just like, I have some ground rules. You don't sleep over my house. I'm not going to get married unless you're going to take my daughter on as fully as I do. And I don't want to play around doing bullshit. I just don't.

People that were frivolous with me well, I don't know. I'm like, well then we're good. Let's just keep it moving. OK.

Julia: Right, right, right. And then of course you met Richard and everything you say about him is just so beautiful to read and such relationship goals, what you had with him.

Dorinda: Richard and I met very unconventionally because I was his real estate agent. And it was literally like four or five or six months later, I had already gotten him the townhouse. And they called and I really thought he was calling. I mean, literally I put them on pause and I said, now he can't take back my commission. Right? Because I was worried. I had no idea. So when he asked me out, it was just unbelievable. I actually couldn't believe that he wanted to go. And I thought, oh, I'll try, I'll go out.

Julia: Then you were able to create this blended family because Ralph and Richard...

Dorinda: Well, we set the ground rules very early on that. And I was very clear about that and he was very amenable to it. And in a lot of ways we had a very traditional marriage and in a lot of ways we didn't, because if his kids sometimes came, like I never got... The apartment I'm living in now is the one I always owned. And I never got rid of my apartment. I literally turned the key to the door and went after I got married and went to live with them. But I never moved a thing except my clothes out of my apartment. And there were many weekends, he'd have his kids. And literally I would be having dinner with him and his kids at a Friday and Hannah and I'd come back to this apartment and we'd spend the weekend together and then go back and meet them on Sundays for lunch because I wanted him to be able to have that time with his kids.

Because it's hard when people get blended families. And I think a lot of times the stepkids of the father get the short end of the stick because Hannah, all of a sudden had their father all the time. So it was nice to kind of, and it was nice for me to have Hannah back here. We really looked forward to it. I was very open about that. Listen, you got to be, especially with a blended family, you have to be willing to compromise a bit because nothing's perfect.

Julia: Yes, absolutely. And you have to be flexible and pick your battles, I think. That's what I always say.

Dorinda: Pick your battles. You got to remember and respect that they had a family before you and it's sometimes hard being the new wife or being the stepchild of, or being the new child and all that comes into place. You're constantly, you're doing a balancing act with it, and then you're a newly married couple. So you want that time together too. And the kids don't get it.

Julia: Right.

Dorinda: No one wants to see mommy's new husband kissing him in the kitchen and his stepkids over so you're constantly like...

Julia: Right. That's it. There's just so much more to juggle when you're kind of trying to create a new family on top of your existing family and figuring out the boundaries and what's OK, what's not OK.

Dorinda: There's a time where like people, single mothers would be in a relationship, but they'll live separately until their kids are grown up. That to me, would be the perfect thing to have an... Imagine this, you lived in an apartment, this one, and next door lived your new husband and his kids. So you got to see each other, whatever you wanted, but...

Julia: Right. I think that's not a bad idea. So, but it is, with all things parenthood, it feels like it's a lot of making it up as you go along and just trying to make those good decisions.

Dorinda: And then just when you get it figured out, you'll turn it all upside down again.

Julia: Right. Right. But reading about your and Richard's relationship really just for me, was like, OK, it's so beautiful. You guys just seem to really kind of connect in this really kind of profound way.

Dorinda: Richard was a great partner. He was a great... We were very ying and yang. He always used to say, the great thing about you and I, Dorinda Medley, is that I'm the mapmaker and you're the executer. And everybody, a map is nothing without the executer. So Richard was definitely more the cerebral one, the calmer one, but he definitely got a kick out of me sort of being the planner, the do-er, the one that always likes to be social and do all that kind of stuff. And we just, I think it worked for me. It doesn't work for everyone, but we all had a role and we liked our roles and it worked like a fine-tuned machine. And then we really just enjoyed each other's company.

I think one of the things that really made me fall deeply, deeply in love with him is that he just loved my daughter so much. It was such a tremendous... I can't say this without not sounding bad, but in a weird way, it was almost as bad a loss for my daughter as it was for me because she loved him. Hannah's father loved him. So we lost, our family and extended family, lost a family member and I lost a husband.

Julia: Yeah. Oh my goodness. I'm so sorry.

Dorinda: I don't regret. I'm not angry. You know, my mother said... I remember one day it was about, I don't know, probably a month after he passed and it was early December. And I was like, I don't even know if I want to decorate this year, which for my family is like a cardinal sin. My mother was like, whoa, now we have a problem.

Julia: Right. When Dorinda doesn't doesn't want to do the holidays, that's when you worry.

Dorinda: My mother said, so what are we going to do here? So she goes, so let me ask you a question. She said with all this sitting around and crying and being, so if Richard Medley, they came to 10 years ago and said, I'm going to give you or eight years ago, and I'm going to meet you and give you, we're going to have a beautiful life together for eight years, I'm going to help you raise your daughter. We're going to do beautiful things together. And then I'm going to have go, would you have done it? I said, yes. She goes, well, that's what you got. Eight years. And you better start focusing on the positive Dorinda instead of... He's dead now. You can't do anything about that. You're alive.

Julia: Right.

Dorinda: And my mother would say to me, get up every morning and take a walk and be thankful. And then you could be sad too, but you got to start focusing on the positive too.

Julia: Wash your face, go for a walk. That's what you were saying.

Dorinda: Well, it's part of life. It's not that she didn't want me to be sad. She just wanted me to say, and I thought about it. It was like, well, my mother has suffered some losses, and I remember her being sad, but I don't remember it disabling her.

Julia: Yeah. But yes, as you were saying, reading Hannah's words that you printed in the book from the funeral were just like so beautiful and so moving about Richard and also just really kind of hit home for me because I was like, yes, that's the goal in terms of being a single mom and dating is like, you want that person to love your daughter and your daughter to love that person just as much as they love you.

You make such clear points about dating and boundaries and just prioritizing your kid. And that really kind of hits home for me.

Dorinda: I just think it's important in life generally, to have good boundaries and parameters. I'm sort of, I know people probably don't know that about me, but I'm actually quite a disciplined person. I like to have fun. I like to be crazy, but at the end of the day, I was never the person that overslept and missed taking Hannah to school. Hannah said that because you know, mom, you have never, I don't think I've ever been awake before you were in the morning. And I took that as such a compliment. I'm like, well, of course, I'm the mother. Can you imagine waking up when your mother's asleep? And I started thinking of my mind with my mother, I'm like, I can't imagine waking up and have my mother asleep in her room. She would have to be almost sick. I'd be like, what is going on here? Is the world falling apart?

Julia: Right. And I think you said it also, when you were dating, you said that over and over again, I'm a mother. So therefore you can't just like schedule a date for me and have that be later today or tomorrow, you've got to plan it ahead and you've got to, we have schedules and we have to plan these things out. And I thought it's so true. Now at times I'm dating one of my bugbears dating is that it'll be like, let's go on a date tomorrow. And it's like, I have a custody schedule.

Dorinda: No, it's like, how dare you? That's what it is. How dare you?

Julia: I love that. Yeah. It does give us a little bit of a magic, super power. We're mothers first. I like that.

Dorinda: I love a good single mother.

Julia: Yay. No, me too.

So your ex-partner, John, he was sort of the opposite, right? So he had never been married and he kind of had no idea how to parent.

Dorinda: Never been married, never had children. Really lived a free life. But after Richard died, I don't think I was... My goal wasn't to get married again. I don't, you know what I mean? I was just looking to smile and laugh and have fun again and yeah. And John was sort of a throwback to my old, like my old time growing up in this very ethnic family. John's fun.

Julia: And I relate to that too, because I think getting married, I got married young and I was sort of an adult right away. So I didn't get to, now I'm in my late thirties and I feel like now I'm sort of doing my twenties in a funny way. It's sort of like these things happen in different times for different people, I think. But yeah, I could see that, that you guys had a fun relationship.

Dorinda: And we still do. Last night he made me laugh about something because he's living out of the state right now, but we stay in touch. I think it's hard to spend a lot of time with someone. I was with him like six years and then not see him again. I just don't roll like that.

I remember someone on the show said, you still talk to him? I'm like, yeah. I've known this person seven years.

Julia: So my last thing I just want to talk about is that you said at 56, I finally feel like I'm living a life I have ownership over. What's your kind of like goals? What's your sort of next thing that you're looking to? And when you're thinking about family, what's your kind of hopes and dreams for your family going forward?

Dorinda: One of the things that I think is most valuable to me now at 56 that I'm so proud of is my freedom. I have freedom, and as a woman to be able to say that—physically, spiritually, mentally, financially—is such a powerful thing. I loved this experience of writing and exploring that part of myself. And I just literally want to keep entertaining and spreading the love and making it nice and meeting new people and just doing what's good for Dorinda. Not Dorinda Cinkala or Dorinda Lynch or Dorinda Medley or the mom or the wife—just me. I get to be selfish with myself for the first time I think ever in my life and it just feels good. It really does.

Julia: Dorinda, again, I just adore you. I think you're so awesome. I'm a huge fan.

Dorinda: Well this is a beautiful a podcast. Thank you for having me.

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Julia: Thanks for listening to my conversation with Dorinda Medley.

Come back next week when we will be talking to fashion designer, entrepreneur, and star of The Hills, Whitney Port, about marriage, motherhood, and the long-lost brother her husband, Tim, only discovered as an adult.

Be sure to follow We Are Family on Apple Podcasts, Spotify, or wherever you listen so you don't miss an episode.

And we'd love your feedback. If you could rate this podcast and leave us a review, we'd really appreciate it. You can also find us online at parents.com/wearefamilypodcast.

We are Family is presented by me, Julia Dennison, and produced by Sam Walker. Editing is by Vincent Cacchione. Thanks also to the rest of our production team at Pod People, Rachel King, Matt Sav, and Danielle Roth.

We'll see you back here next week for more We Are Family!