An idyllic childhood, meant-to-be relationship, and life as a mom with the hope of expanding her family—The Hills star Whitney Port lets us in on her family life.

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Whitney Port

Fashion designer and star of The Hills and The City, Whitney Port chats with host Julia Dennison about everything from her happy childhood and big family, the passing of her dad, knowing her husband was "the one" on their first date, miscarriage, and the complicated feelings that go along with pregnancy, breastfeeding, and being a mom.

"The postpartum experience for me was really, really challenging," says Port, whose son, Sonny, is now 4. "I didn't know who to turn to .... None of my really good friends had had babies yet or were in that phase, and so I had a very, very difficult time."

Between a strained relationship with breastfeeding and exclusively pumping, stress and guilt was all-consuming. "I wasn't even really focusing on my relationship with my baby or what my baby was even up to," says Port, who has been sharing her experiences of feeding firsthand as a contributor to Cluster, a new digital community supporting parents making feeding decisions for their babies.

Now, after suffering three miscarriages, Port has mixed emotions about expanding her family. "Because it's something that you want but you're putting yourself through this emotional and physical strife. And it's like, why am I doing this? It's very confusing."

Check out Episode 3 now for more of Dennison's conversation with Port!

Upcoming episodes and topics this season include:

  • 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 3 right now:

Plus, follow along here:

Whitney: …To me family is home.

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Julia: Hello and welcome to We Are Family. We are here with Whitney Port, a CEO, fashion designer, entrepreneur, creative consultant, digital influencer, and TV personality. You will all know her from the reality show The Hills and subsequent spinoff, The City. She has a podcast called ‎With Whit and a fashion line called Whitney Eve. She lives in Los Angeles with her husband, Tim, and her son, Sonny, who just turned 4. Whitney, welcome to We Are Family. Thanks for coming on.

Whitney: Of course, I'm so happy to be here and so excited to chat with you guys.

Julia: Oh, we're so thrilled to have you. So as you know this is the podcast all about family, and we want to hear all about your family today, but also I wanted to kind of dig into a little bit of your background. So you grew up in a large family, right? You were one of five siblings, is that right?

Whitney: Yes, yes. So I am the middle child of five kids. My brother is the oldest named Ryan, then I have an older sister Ashley, and then me, and then my younger sister Paige, and the youngest sister Jade. And four of us are in L.A., and one of us is in Chicago.

Julia: What was that like growing up as one of five? Did it feel like it was hard to get your voice heard? Was it really busy? Paint us a picture of your childhood a little bit.

Whitney: So to me my childhood was kind of idyllic. I lived in this great, happy, big family. Our grandparents helped raise us, my parents were happily married. It felt kind of like heaven. And really with the five kids it was rare, like we didn't really fight so much. Some of my other sisters fought but I think for me my personality has always been one to steer away from the drama. But I do remember definitely sometimes feeling a little bit left behind in a way. Not like it was ever on purpose, but feeling like my mom was always late to pick me up or I don't know, just like something was, I wasn't necessarily probably getting the attention that Sonny, my only child, gets for sure.

But I don't really ever feel like I wasn't heard, I always felt like my parents did a really good job of sitting down at the dinner table every weeknight and making sure that everyone got a turn.I think my parents raised us, and a lot of us obviously being girls, to be really strong, loud women. And so we never really had a problem getting our voice heard. And I think that's something that has been integral to us being strong women today.

Julia: I love that. And so being one of five, how did that kind of mold your vision of how you wanted to be a parent?

Whitney: So I think when I was younger, when I was like a late teenager into early twenties, I think I was always like, I'm going to have a big family for sure. I love my big family so much; I'm so connected to them. It's just the most fun. I never went to summer camp; summer camp was always just at our house. And then I think as I started to realize that I wanted so much more out of life for myself, which included a career that really was very, took a lot of hard work. And I wanted to be an entrepreneur. I had that entrepreneurial spirit because my dad had that and I think it's just sort of in my blood. And I realized that maybe a large family wasn't something that was going to allow me to be super happy and balanced.

So once Timmy and I started talking about kids we were always just on the two to three train. And we still haven't made a definitive decision, we always try to keep things loose and open-ended. But I don't know, after having one I don't know that I could have more than three.

Julia: I feel you, I have one daughter and I am very happy with that. I also thought that maybe, I mean I'm in a different situation because I'm a single mom so that sort of takes some more thinking. But no, the more I kind of, it's like a mindfulness thing for me, kind of just experiencing what it's like to have just the one child and appreciate that for what it is. There's a lot of perks.

Whitney: It's so true. There are a lot of perks and there's so much of me that would love to keep it as one. There is so much of me that feels like everything is just so wonderful and so beautiful, and life is for me personally and in personal health, my well-being, I finally kind of feel like I'm figuring things out and figuring out how to be happy while having a really full, busy life. And I'm like, oh my God, why kind of ruffle the feathers? But then there's just that other part of me that says do I see myself in 20 years looking back and possibly regretting not having a little bit of a struggle to have the second, and have a hard couple of years to then be able to give Sonny a sibling? Which he's started to actually ask me for which I never thought he would, but he did.

I hope that I'm not alone in this, it would make me feel better knowing I'm not alone. But I think that yeah, it's hard, it's hard to struggle. And it's hard to make plans and then think about wait, I don't know if I want to do what I originally said I want to do, or things aren't going the way that I thought they were going to go. I'm sure you didn't necessarily think, and not to get all personal...

Julia: No please, that's what we're here for.

Whitney: But that you were going to be a single mom, right?

Julia: Yes, absolutely. I think parenthood and my journey into parenthood, and I think for all parents everywhere and moms, it's such a lesson in not being able to control your life. We all know that we don't have real control over our life. I mean we can influence it as much as we want to, but at the end of the day it's going to be what it's going to be and you kind of have to just go down that path a little bit I feel like.

Whitney: 100 percent. I mean my sister, she just had a baby, and the baby flipped like the week before she was due and she ended up having to get a C-section. And she was really torn up about it even though you know logically that that is going to be an option. But when it actually happens and you weren't prepared for it or you didn't think that that was how it was going to go, you immediately feel this loss of control that's very unsettling. And I think that is so much of what the beginning stages of being a parent is about. And part of me wanted to be like, welcome to parenthood, it's not ever going to go exactly as you have outlined.

Julia: Yes, I think that concept of that birth plan is the very first moment I think for a lot of parents where they realize you might as well just throw all that planning out the window.

Oh my goodness. Well that's exciting for your sister. Congrats.

Whitney: Yeah, we're so excited.

Julia: And I think the conversation about siblings is an interesting one because I feel like I often think about what would be like for my daughter to have a sibling as she grows up. But becoming an adult I think your relationship with your siblings can really, really shift and change.

Whitney: I mean 100 percent. Well I've been close with my sisters always, and I think really when we were younger we were like inseparable. And then obviously we got older, and we got married, and we're starting to have kids, and everyone has their separate lives. But I think what has been the most helpful is to have that support system when… I don't know if I'm allowed to swear on this podcast...

Julia: Go for it.

Whitney: Like when shit happens and the only people that really understand how you're feeling is your family. Like my dad passed away in 2013 and I can't imagine not having them these past eight years to have all those memories to relive and to have other people that knew him as much as I did so that we could keep his memory and spirit alive in order for our kids. And yes, it's really, really, really special but it's also really, really complicated.

Julia: Oh yes, absolutely.

Whitney: Like my mom is always saying, it is so hard having adult children. She never knows exactly when to step in, when to give an opinion, when it's warranted. And I feel for her, I feel for her.

Julia: That's something that's going to be in our future, navigating those relationships.

Whitney: For sure.

Julia: Yeah, but I mean it's useful, too. I mean my mom, when I had my daughter there was so much about my relationship with my mom that I understood better once I became a mom. Did you find that too?

Whitney: Oh yes, 100 percent, 100. And I think that it allows me to know her in a deeper way. And I think that it makes me really appreciate her so much more. But it's also sometimes I feel a little guilty being an adult and now having my own family and tending to them, and feeling like I'm leaving this other portion of my family behind or to the side. It's a weird thing coming from a big, and you don't even have to come from a big family, but to start to form your own family and to separate from your original family, it takes some time to feel OK about it, yeah.

Julia: Navigating those boundaries like who hosts Thanksgiving? Where are the holidays? Who's the kind of main host of the holidays? Absolutely.

Whitney: It's so important, it's so important. And I think it's things that we should think about more, and that setting boundaries is totally OK when it comes to family and not something to feel guilty about.

Julia: It's important, and I think it strengthens your relationship with your family. So it is important to do even sometimes when it's hard. But let's go back in time a little bit and talk about your mom and your dad. So when you started on The Hills in 2006 what did your parents think about it? Did they support you? What was their kind of approach as you launched your reality TV career?

Whitney: Yeah, so my family, they were totally supportive. We grew up loving reality TV. Like we sat on the couch together watching American Idol and The Bachelor. And I think really my parents trusted me and they trusted the person that they raised to navigate this world in a decent way. And so they wanted me to do whatever I felt comfortable doing.

Julia: I see that. So if Sonny were to turn around and say, "Mom, I want to be on TV," would you let him?

Whitney: That's so hard. See, I feel like there's so many depending factors. One, it depends on what kind of kid he is. I mean I hope that he obviously has a good head on his shoulders, and has a good character, and makes decent decisions, and doesn't want the fame just for the sake of fame. Obviously if he is not that then I urge him not to do it. I would probably tell him not to do it. But honestly I wouldn't tell him not to if I felt like this was something that was going to help lead him to a world that he wants to be in, maybe a career opportunity, I don't know. It's hard. Part of me wants to say, no, no, no, don't do it, steer away from it. But I was able to really have a positive experience and grow a business out of my passion, and don't have any regrets about it. So it would be hard for me to tell him not to, it just would be so dependent on what kind of kid he is.

Julia: Makes total sense. And that's the thing I think about having kids—they're their own people, they have their own personalities. That's always a big lesson I think for us parents.

Whitney: Yeah. You have to metaphorically cut the cord in lots of different ways every single day in order for them to form their own identity, and have some sense of independence, and really be able to discover the world, and learn what feels good and cozy to them.

Julia: So tell me a little bit about how you met your husband, Tim. Did you know right away that you wanted to parent with him, what were your kind of first impressions?

Whitney: Yeah, so I really believe it was love at first sight for me and Tim. We met in New York City through a mutual friend, and then through that mutual friend he ended up getting a job as a producer on The City, the show that I was on. And so we just became really close because when you're filming a TV show it's like summer camp, you're with each other all the time. And for me I was even closer to the producers than I was the actual cast. So we just became really close and we were obsessed with each other but never acted on anything. We had this Blackberry Messenger relationship that we just were, we were really, really good, flirty friends. And it wasn't until the show ended that we actually were like OK, let's do this.

The first night we decided to become official I knew he was the one I was going to marry. I knew that once Timmy became my boyfriend that that was it for me. And I knew that we would have children. I knew he just had this insanely loyal, trustworthy, lighthearted humor that was infectious. It was like I knew that this man would make me laugh for the rest of my life.

And obviously his character, and his heart, and his sense of right and wrong, and the fact that I can really trust him and tell him anything and believe that what he's saying to me is leading me in the right direction. All those things obviously are so important in values and choosing the person that you're meant to be with, but it was really I think his humor that I was just like, I am obsessed with you. If you can make me laugh for the rest of my life I feel like I'm set.

Julia: I love that, that's so sweet. So then you were engaged in 2013 but that was also the year that you lost your dad.

Whitney: Yes, yes. That was really, really hard for me because it felt like it was supposed to be the happiest time of my life. Like about to be getting engaged and really starting my life as a 28-year-old, and then this happened. And this experience really bonded Timmy and I together. Like this experience can sometimes I feel like either make or break a couple, and my sister had a similar experience with her boyfriend that she had literally just started dating. And he moved in with she and my mom right after my dad passed away. And I just feel like because we had such an amazing father who was such a wonderful model of grace, and silliness, and a beautiful heart, I think that we were able to then know what we wanted in a man. And I feel so lucky for that. And I think that my sisters and I have found just such amazing men that my father would be so, so, so proud and happy about.

Julia: Sonny has just turned 4, but let's go back to when you first found out you were going to be a mom. Was it a planned pregnancy or were you surprised?

Whitney: It wasn't super planned but I had been off my birth control and it happened pretty fast. And yeah, I was pretty shocked and I knew nothing, I knew nothing. I was terrified. Like the thing is I was not so terrified of the birth and having the baby really, it was just like I was terrified of the pregnancy. I was just so scared of the unknown, of what was happening to my body.

And also I was really, really, really nauseous for like the first 18 weeks, so that just made me not feel very connected to the pregnancy either. I also didn't find out—we never found out if it was going to be a girl or a boy, and I love that we had that surprise. But I wonder if not knowing the sex made me feel some way less connected to it. So yeah, the pregnancy portion of my life was definitely not my favorite. But I'm trying to look at it with more of a growth and learning lens, because I think that once you've kind of gone through it you can have, I don't know, an easier attitude about it I hope.

Julia: No, yes, absolutely. It is that great transition into parenthood like we talked before, that loss of control, your body's kind of taken over. I mean half of it is worrying about the baby, half of it is worrying about your own self. And then you're kind of projected into early motherhood, which is a whole other trip.

Whitney: Yes.

Julia: What was your experience at that postpartum period and early motherhood?

Whitney: The postpartum experience for me was really, really challenging. I didn't know who to turn to. My mom who had five kids—who you think that she would kind of be your guide—like she really, I felt like, she was scared to tell me what to do a little bit. Like breastfeeding was very, very, very hard for me, and it was never really hard for her. And so I don't know, it was like where do you turn?

None of my really good friends had had babies yet or were in that phase, and so I had a very, very difficult time. I exclusively pumped for six months. I got mastitis three times. I continually told myself after getting mastitis that I was going to quit breastfeeding, or pumping, excuse me. And I didn't because I was just too held back by the guilt and held back by the unknown.

Julia: So much emotion goes into it.

Whitney: Exactly, so much emotion. And so that first six months of Sonny's life is just a fog for me because of that. I think that I was struggling with that whole relationship with breastfeeding day in and day out. I wasn't even really focusing on my relationship with my baby or what my baby was even up to.

Julia: Yeah, completely.

So talking about sort of another difficult subject, you've spoken openly about the miscarriage that you had in 2019. And as somebody who's also gone through miscarriage and also looking at the statistics at how common they are, I always say thank you to anybody who's in the public eye for speaking out about these things that a lot of people are going through in silence. But you did write at the time that your identity was really shaken, and obviously it can be a very traumatic experience.

Whitney: I unfortunately had two miscarriages and had really different reactions to both of them. My first miscarriage, I was about 9 weeks, and I was oddly kind of relieved when it happened. And it made me feel like such a monster. And that was one of the times really when I opened up about all that on my podcast and was so nervous for what people were going to say, because I had really never heard anybody feeling that way before. Like I had always heard that miscarriage was obviously the most devastating thing of all time. And I want to be sensitive to that but I didn't necessarily feel that way and I felt so horrible. So it was a very, very confusing time for me and it was a very weird grieving period.

And then the second time I was so ready for it to happen. I was so excited. We were ecstatic we were pregnant, and then again around that same time—it was like 8 weeks. We started to realize that it just wasn't a healthy pregnancy and I was devastated. It was like all my grief feelings from my father came and crashed over me. It was just an immense, immense amount of grief. And just this feeling kind of like emptiness and of like, I don't want to do this again. I don't want to put myself through these complicated, confusing feelings anymore. And so that was the end of last year. And then now in May I had a chemical pregnancy. And so at this point I'm like...

Julia: It's so frustrating.

Whitney: It's so frustrating. It's so frustrating because it's something that I really do want. We want it to happen but I'm so conflicted. And sometimes I wonder if that confliction is making it harder for my body to actually make it happen. And I don't want to go the route of like the timing everything and the IVF. The thought of that sounds so scary to me.

Julia: Of course, of course. But I think you bring up a really good point that so much around miscarriage is that personal guilt, and that feeling that you could influence it one way or another. We've done so much reporting on Parents.com and in Parents magazine about how there's truly just this, these things, miscarriages happen. It's not your fault as a mother, and as much as you can take that guilt off of your shoulders. But yeah, I mean you really highlight that broad range of reactions and feelings people can have around miscarriage and that trying to conceive journey. It messes with your mind in so many different ways.

Whitney: It really does, it really does. Because it's something that you want but you're putting yourself through this emotional and physical strife. And it's like, why am I doing this? It's very confusing.

Julia: Yeah. So I wanted to ask you about one other thing, because this is a podcast about family and interesting complexities behind family. So is it true that Tim found out he had an older brother he didn't know about later in life?

Whitney: Yes, yes, yes.

Julia: What was that story?

Whitney: Yeah. So long story short, his mom had put his older brother up for adoption when she was younger and they ended up finding each other through a website about, gosh, I think it was like maybe six years ago now. And we now have this amazing family, they live in Georgia. So we have his brother, and his wife, and their kids, and nephews and nieces, and just this amazing, new, warm family that has been such a gift. I feel like you don't necessarily hear stories like that.

Julia: Yeah, found some more family. That's awesome.

Whitney: Yeah, the found family is the best because you don't have the shticks of the past history. It's all new family.

Julia: Right. So you've been out to visit them?

Whitney: Yes, yes. We went this summer. We went out to visit them where they live on a lake in Georgia and it was amazing. And we spent my mother-in-law's 70th birthday all together in Montana. And it's really, really, really wonderful. It's just such a gift and I'm so happy for them.

Julia: Cool. Oh my goodness, I love that. That is just so awesome, what a cool story. And so then the last 18 months I think has just been some of the most challenging times to be a parent, what was the pandemic like for your family?

Whitney: It was really a mix. I think that for the most part we were extremely lucky, we were healthy, our family stayed healthy. Parts of my family were really, really isolated, and so that was challenging. But I think for my family, it finally forced me to take a look at my mental health and take a look at a lot of things that I was pushing down and not dealing with, and thinking that just because I had mostly good days that I was fine. But I think that it really forced me to take a look at my shadow, because we didn't have time, we didn't have the distractions. And I think for me it strengthened my family. The three of us are operating in such a smooth way and dynamic right now, and really being so thoughtful about the way that we're talking to each other, that that has been a blessing.

Julia: And I think for a lot of people the pandemic kind of shifted their values and their kind of hopes and dreams for their family. What kind of hope do you have for your family in the future? What are your kind of priorities?

Whitney: For my family I think it's just maintaining the happiness that we have now and really being present in all these beautiful moments, because I think we will look back and look at a lot of these moments spent together as the best of our lives, and I think it's really about taking those mental snapshots and just maintaining that presence forever.

Julia: I love that, that's beautiful. Well Whitney, thank you so much for coming on We Are Family. We were so glad to have you, it's been so great to chat.

Whitney: Of course. Thank you so much for the opportunity. You're so warm and lovely.

Julia: Thanks for listening to my conversation with Whitney Port.

Come back next week when we will be talking to reality TV super couple Ashley Iaconetti and Jared Haibon about their roller coaster romance, their families' reaction to their relationship, and how they are preparing to become first-time parents later this year.

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We Are Family is presented by me, Julia Dennison, and produced by Sam Walker. Editing is by Vincent Cacchione, and 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!