
Getting Sticky With Whitney Port
Photos by Lindsey Molk, Words by AnaMaria Glavan
Whitney Port is one of five children. If you believe in birth order, she’s a true middle child, and the go-with-the-flow attitude she developed early on has shaped much of her life. That “loosey-goosey” POV feels almost in direct opposition to her long-running fertility journey where every variable has had to be meticulously crafted.
She became pregnant with her first child after just two months of trying at 32. Now, at 41, a seven-year fertility struggle has prompted her to reflect on her upbringing—and the version of motherhood she once assumed would be hers. While she wasn’t necessarily planning on having five children (her husband, Timmy, is also one of four), what she didn’t anticipate was how difficult it would be to complete the family portrait with a second. And while she’s profoundly grateful to have a healthy child, her family still feels incomplete. This truth doesn’t negate gratitude.
We’re proud to interview Whitney Port, who has spoken openly and candidly about her fertility journey to help other families in similar situations feel less alone. She has also had to shoulder the burden of online bullying because of it (editor’s note from STJ to online bullies: literally, why?). Along with that has come a barrage of questions that can feel, frankly, rude—and anyone with a nosy mother-in-law or a good-intentions-but-blunt friend understands what it means to have to repeatedly explain something that feels traumatizing.
Below, we spoke to Whitney about “feeling like a loser” in her first trimester (same), a fertility journey that has led to surrogacy, and—because we know you’re wondering—yes, Whitney Port, style icon, drops her son off in sweatpants, too.


How does the Full House theme song go again?
I grew up one of five kids and I was very, very close with all of my siblings. I’m the product of a big family. When it came to having my own kids, I was initially very loosey-goosey about it; that’s my personality to begin with. I’m the middle child, so my baseline is to go with the flow.
Timmy is one of four too, so while we knew we wanted kids, we decided to evolve on our own timeline. I went off my birth control when I was 32 and got pregnant within two months. It was so lightning quick. Importantly, I wasn’t planning for it—I let it all evolve organically. And I think the ease of that is what allowed it to happen so easily. But who knows?
It didn’t hit me that I was becoming a mom until about two months into my pregnancy, when I started to feel really sick and felt a lack of control over my body and emotions. It became very real after that, and the idea of becoming a mom became difficult for me in that first trimester. I didn’t like the lack of control over my body. I was sick every single day. I had plans for myself, goals, an active collection I was launching in December. I started to feel sorry for myself. Honestly, I felt like a loser. I couldn’t show up, and it affected my confidence. It affected how I viewed pregnancy and motherhood. I became sort of resentful toward it.
So my pregnancy, while extremely healthy and physically perfect, was a hard time for me emotionally. I am not the kind of person who’s reading everything, doing all the courses, or talking to everyone. I wanted to hold onto my identity. Looking back now, I realize I needed to be somewhere in the middle. Yes, I want to parent based on who my child is and not listen to what everyone tells me to do. At the same time, I do think that a little more education, preparation, or even conversation with other women would have made it less scary.

"I started to feel sorry for myself. Honestly, I felt like a loser. I couldn’t show up, and it affected my confidence. It affected how I viewed pregnancy and motherhood. I became sort of resentful toward it."

You don’t have to follow self-imposed rules (i.e., it’s perfectly reasonable to stop pumping after a third round of mastitis)
My son is eight years old, and I definitely feel more sure of myself now. I hope that gives some relief to new moms. People get scared that as they get older, it gets more complicated or scary, but for me, being able to communicate now is so freeing. I was much more scared of what I didn’t know back then, of being in the middle of not knowing what the baby needed. And honestly, the hardest phase of all for me was breastfeeding. Everything since then has felt like a breeze because breastfeeding was a full-on nightmare for me. It’s something I won’t forget, and I’ve told myself not to forget.
It’s not always what you see in the movies or what you envision this natural thing to be. He was on my boob almost every second of the day while we were in the hospital. I went home with bloody nipples, had a breakdown, and thought, I don’t know if I can keep doing this. Then came the guilt around not doing it. I ended up exclusively pumping for six months because pumping was less painful than latching. But because the pump isn’t as good as a latch, I got mastitis three times. After the first time, I told myself that I would quit if I got mastitis again. Then I got it again… and still didn’t quit.
Six months doesn’t sound that long but it felt like a shit ton of time to me. If I have one regret, it’s that I put a time limit on pumping and told myself I needed to do it for that long because I didn’t need to do it at all. I’m not more proud of myself now that I did it for six months. I wish I had stopped earlier and enjoyed that time instead.
That being said, comparing our personal journey to anyone else’s is illogical because we’re all so different and our babies are so different. It’s important to create space to talk and share, but at the same time, no one can give us answers because they don’t know what’s right for our baby. I wish I had an answer for how we, as women, could talk about this in a less judgmental and less self-serving way. If someone is sharing their story, it’s natural to ask why or how. But I think it depends on how you ask and how close you are to the person. You have to know your boundaries.
At the beginning, I was trying to pull for data, asking things like, How long did you breastfeed? Are you breastfeeding? And then I realized that when people asked me those questions, I would shut down inside. I would think, This isn’t something people should be asking. It’s similar to when people ask, Are you going to have a second? I understand these questions come from curiosity. We’re all trying to pull data and see what might work for us or might not.
"Six months doesn’t sound that long but it felt like a shit ton of time to me. If I have one regret, it’s that I put a time limit on pumping and told myself I needed to do it for that long because I didn’t need to do it at all. I’m not more proud of myself now that I did it for six months. I wish I had stopped earlier and enjoyed that time instead."

“It feels like there’s a piece of my motherhood pie that isn’t complete”
I don’t think motherhood looks like what I imagined. I never thought I’d be a mom to an only child. I always knew I wanted more than one. I didn’t picture this, and that’s been a little weird for me. My identity as a mom doesn’t feel fully solidified yet because I feel incomplete. I really do.
I’m trying to come to a place of acceptance with having one child, because I haven’t been able to get pregnant with a second. We’re still on the journey and still trying. But it feels like there’s a piece of my motherhood pie that isn’t complete.
I feel insecure sometimes as a mom because of it. When I’m talking to other working moms, I don’t always feel like I’m on the same playing field. This sounds awful, but there’s this feeling like one isn’t enough—or that it’s not as hard, or not as much to balance, or not the full picture. And I carry that insecurity. I’ve done a lot of work around it. Most of the time, I’m able to tell myself, Okay, if it’s just the three of us, that is wonderful. It really is. I’m so grateful that we were even able to have one. But there’s still a part of me that doesn’t feel complete.


"I don’t think motherhood looks like what I imagined. I never thought I’d be a mom to an only child. I always knew I wanted more than one. I didn’t picture this, and that’s been a little weird for me. My identity as a mom doesn’t feel fully solidified yet because I feel incomplete."

Knowing there’s no “easy” way is both stressful… and reassuring
It's been seven years of trying since Sonny. I got pregnant about a year after he was born, and then it was miscarriage after miscarriage after miscarriage. I was getting pregnant but the pregnancies weren’t sticking. Eventually, I was told my chances would be better with a fertility doctor. I went to one who came highly recommended and started the process of egg retrieval, freezing embryos, and IVF. I went through the retrieval and was about to do a transfer when I got really sick with a stomach virus. I was throwing up nonstop, I tore my esophagus, lost a lot of weight, and ended up not being able to do the transfer at all.
After I physically recovered, I realized I had hit a physical and emotional rock bottom. All the stress from years of trying, the miscarriages, the anxiety around the transfer not working—it had been four years at that point. That’s when Timmy asked if we would consider surrogacy. I had been thinking about it but didn’t feel comfortable saying it out loud. Frankly, I was afraid of the judgment.
I felt like I hadn’t done everything yet, so I didn’t deserve that option. I rejected the idea for a while. Then I started talking to people who had used surrogates and had similar experiences. I decided to take my power back and see it as a privilege; I don’t need to keep putting my body through this after six years of trying. I was 41 and I was losing myself. We found a surrogate and did two transfers with her, both of which failed. That was about two years ago. And the whole process—finding a surrogate, doing transfers—everything takes so long.
Then she’s pregnant for 11 weeks, and then we lose the pregnancy. The process is all so long because each step along the way takes so much time. So last year, since the first surrogate didn’t work with the first two embryos, we decided the best thing to do was to change all the variables. We switched doctors, did a new round of egg retrieval and embryo freezing, and found a new surrogate. Now we’re at the point of contracts with the surrogate and hoping to do a transfer by the end of this year. That’s where we’re at right now.


" I realized I had hit a physical and emotional rock bottom. All the stress from years of trying, the miscarriages, the anxiety around the transfer not working—it had been four years at that point. That’s when Timmy asked if we would consider surrogacy. I had been thinking about it but didn’t feel comfortable saying it out loud. Frankly, I was afraid of the judgment."

A note to bullies from STJ: literally why?
During this whole process, I’ve thought about how much easier it would be if I just went in and did the transfer myself. And I don’t want to say it’s so much harder, but the process of finding another person, doing all the checks, making sure everything is right is a lot. It’s a big emotional journey as well.
It feels like a bit of a loss for me, of what I’m giving up. It’s hard in a different way. I don’t want to say one path is harder than the other at all. It’s just different. And usually, when I share motherhood or fertility-related things, the response is overwhelmingly supportive. That’s why I continue to feel comfortable being vulnerable. I really do think, as a society, we’re getting better at having these conversations and respecting boundaries.
But recently someone wrote something really terrible to me, basically implying that I was too afraid to ruin my body to get pregnant. And I thought, If only you knew. I usually don’t respond. I’ll block people and move on. But for some reason, this one really got to me. I ended up responding, and Timmy got involved too. This person has written things like this to me before.
My response was essentially about how I’ve been vulnerable and shared my entire story for years, and how insensitive it is to bully someone based on knowing absolutely nothing about what they’ve been through. It really stuck with me because it was so fresh: we had just gotten off the phone with our surrogate and her husband, and we’re so deeply in this for the right reasons. It’s strange for anyone to comment on how someone else is living their life or treating their body. I really thought we’d come further than that.



"But recently someone wrote something really terrible to me, basically implying that I was too afraid to ruin my body to get pregnant. And I thought, If only you knew. It’s strange for anyone to comment on how someone else is living their life or treating their body. I really thought we’d come further than that. "
First comes love
Timmy and I are best friends and we try to make everything fun. That’s the root of keeping things fresh and positive. Throughout this whole journey, he’s understood that it wasn’t about him. He made space for himself—he has friends and support where he needs it—but he always knows how to be there for me while leaving space for my feelings. He doesn’t pressure me to feel a certain way. If men could learn anything, it’s that we’re not looking for them to solve our problems or come up with all the solutions. We just need them there to help us game plan, to listen.
As for our parenting styles, I’m definitely more lax. I’m not going to ask Sonny to brush his teeth every single day. Timmy sometimes has to be more of the disciplinarian… but for the most part, we share the same parenting ethos.
You never know what a baby is going to bring out in you. It’s a version of love you’ve never felt before, and it can bring out extremes where you’re like, Wait—who am I? It’s confusing. You start wondering if you’re behaving the right way or making the right decisions. The most important thing is listening to your gut and doing what feels right for you as a parent because only you really know your child. Timmy tends to be more logical and realistic whereas I’m very emotionally driven. That balance works for us.
I had to go to New York for three days a month after Sonny was born. It was like ripping off a Band-Aid. I had to quickly learn that I wasn’t the only person responsible for this baby, and that helped me in creating healthy boundaries right away. Both with Sonny and with work.
And listen, I’m never going to tell anyone what to do. I would never tell a mom to just rip the Band-Aid off and leave town a month in. But I do think there’s something to be said about figuring out healthy boundaries so you don’t hit burnout and become resentful of the life you’ve created. Especially at the beginning, when the baby doesn’t even have a clue if you’re gone or not. A six-month-old might miss you for a second, or when you get home they’re like, oh, I missed this. But they don’t have a frame of reference for time. They feel safe. They feel cozy. They feel loved. They’re with their dad. They’re not even aware. Someone once told me that when they’re young is actually the time to travel—if you have that luxury—and let aunts, uncles, and grandparents bond with them.


Sweatpants are the most acceptable form of school drop-off attire, actually
Not only has your body changed physically, but you also start asking yourself, How am I supposed to dress as a mom? That’s the question we need to stop asking. Instead of What should a mom wear? it should be: How do I want to feel today? What do I want to wear today? We’re still the same person. We still have style. We still have our own taste. It’s really just about figuring out how to dress a new body that you may or may not feel totally comfortable with for a while.
For me, at the beginning, it was a lot of mini dresses—balloon shapes, mumu-type dresses that were really short. Big blazers, baggy jeans, hiding under layers. Oversized jeans are always a good move. Not even investing—just grabbing a couple pairs of like $80 Levi’s that are five sizes too big and letting them grow with you.
That said, life is easier when you have a reliable uniform. A T-shirt, a V-neck sweater, and a pair of baggy Levi’s. Do that in a bunch of different colors. I had Coco Schiffer on my podcast and she said Cos makes the best trousers because the waistband adjusts tighter or looser.
I started on a TV show at 20, and I’ve always had a very random schedule and been lucky enough to make my own hours. Sometimes I don’t get dressed at all. Yesterday I stayed in my pajamas—which are basically sweats—all day long. It can be a little depressing, but it’s real. If I have to get dressed, I will. When I’m in New York, I’ll get dressed just to walk and get a coffee and actually enjoy it. Most of my work is from home. If I’m being honest, in L.A. I don’t really get dressed. I’ll drop Sonny off without a bra, in a crewneck sweatshirt and fuzzy pants.
