Thirteen Years Later, a Teen Mom Finds Motherhood

When Sierra Dressing got pregnant at 15, she chose to carry the baby to term. Now, at 29, she’s pregnant again, but this time it’s on her own terms.

By Saira Khan

On a recent Tuesday morning, Sierra Dressing, 29, posted a gif on Facebook, offering bystanders a glimpse into a joyful moment. In it, her parents, husband, and in-laws are seated on a couch as she emerges wearing a grey t-shirt. “It’s not a food baby,” it read. In the few short seconds that she allows virtual bystanders in, her mother and mother-in-law jump up from their seats, to give her a hug that we do not see. Her sister-in-law bursts into tears, her father and husband grin. Sierra’s baby is due in October. It will be the first baby she raises, but it will not be the first one she gives birth to. She had her first child in 2004 when she was 15.  

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In full disclosure: Sierra and I are friends, which is why her post appeared at the very top of my Facebook feed. We met in college and I was instantly drawn to her warm personality. She is generous, the kind of woman who will buy all of her friends shots just because. She wears her emotions on her face. She has a porcelain white complexion and light brown hair. She laughs often, even when she is talking about something that makes her uncomfortable.

Sierra grew up in southern Maryland. She describes her childhood as uneventful and says that when she entered her teens she was “the type of girl whose friends wore all black.” She started high school with excitement and apprehension, and quickly found her place in a social circle.

When Sierra was 14, she met a boy. His name was Colin*, he was 16, and she thought he was “incredible, amazing.” And then it got even better: he liked her back. “I did this thing where I fell down on my knees in the snow, and did these air punches with a huge smile on my face when I found out.” 

“He was my first everything,” Sierra said. They had sex for the first time about six months into the relationship and “it was magical.” But as their relationship continued, things started to change. They’d smoke marijuana and often skipped school together. “I was making all kinds of really rash and ridiculous decisions. But I really loved him,” she said. “So, I was just like, ‘This is what you do when you’re with someone. You just go and be with that person.’”

After several months of being sexually active, Sierra missed a period. She was 15 by then. “I wasn’t ready to accept that [pregnancy] was a possibility. I kind of kept pushing it back in my brain.” She took a test, months later, after confiding in a friend. It came back positive. “I remember feeling totally incapable of thought or speech, or just feeling totally deflated,” she said.  

Most of her friends had opinions: some told her to keep the baby, others told her to get an abortion. “I didn’t know what to do, adoption didn’t even cross my mind, but I knew I couldn’t be a mother,” Sierra said. “I could barely manage my own life, how was I supposed to take care of someone else?”

Sierra decided to see a doctor at a nearby clinic before she told Colin about the pregnancy. It was there that she discovered she was further along than she had thought. She was in her second trimester, which meant she would have to undergo a surgical abortion that would cost hundreds of dollars and would need her parents’ permission. Colin wasn’t thrilled by this information either. When she told him about the pregnancy he said if she kept the baby he didn’t want to be involved. “I was absolutely crushed and heartbroken and pissed off,” she said.

“I remember feeling totally incapable of thought or speech, or just feeling totally deflated.”

At this point, Sierra hadn’t told her parents yet. “I knew I had to tell them but I was not exactly the nicest person in my house. I was in my teenage rebellion stage,” she said. “So I thought ‘Oh great, I’ve just been this massive shithead to my parents for the past like two years basically. And now I’m going to have to, you know, come to them with this crazy world-changing information.’”

Sierra’s father was away on business at the time, so she spoke to her mother. They were on the front porch when she broached the subject. “Mom looked at me and my eyes were already full of tears. I’m about to start bawling and she’s like ‘You’re pregnant?’” Sierra started sobbing uncontrollably. Her mother hugged her and told her it was going to be O.K. A sense of relief flooded over Sierra, who, in that moment, realized how alone she had felt. “She was the first person to do that. She was the first person to say that,” she said.

It was an incredible moment because “you spend your whole life hearing that your parents love you and then when it was put to the test, they really  come through for you in a major way,” she said. Her father’s reaction was less graceful. “He said ‘oh shit’ a few times but then he calmed down.”

The next day, after her father came home, they talked options. Sierra made it clear to her parents that she was not ready to be a mom, but when the conversation came to abortion, her mother asked her to consider adoption. I didn’t necessarily want to have this procedure either,” Sierra told me. “All of the options seemded equally shitty in my head.” After some consideration, they decided on an open adoption. “I wanted the ability for the child to be able to ask me any questions they may have or, you know, come hang out with me if they ever wanted to,” she said. “I wanted to be around if the kiddo ever wanted to talk to me.”

When Sierra told Colin about her decision, he broke up with her. “At the time I was like ‘fuck you dude,’ but now, I do really understand. He was 17 years old. It’s a lot.” But still, “I was heartbroken. I was really, really sad about it,” she adds. And she didn’t just lose her boyfriend. Her group of friends also started thinning out. Some people told her she was “shitty” for “having a baby and then just giving it away,” while others told her she should have gotten the abortion.

Sierra’s extended family also tried to get involved. A few people tried to convince her to leave the baby in someone else’s care until she was ready to a be mother. When she stood by her decision, one of her relatives sought counsel to see if they had any legal claim over the baby. “I was actually very upset with them for quite a bit. But I guess we all have slightly crazy family members.”

Sierra started the adoption process shortly after talking with her parents, which involved reading packets of letters from prospective families and their character witnesses. One of those packets“it was quite hefty”came from Gibby and John, a couple who lived in California. “They sounded so warm and open… they actually sounded a lot  like my family,” she said, which is why she decided to meet them.

A few weeks later, in June, Gibby and John met with Sierra at a restaurant in Georgetown. “I had pretty much already made up my mind before I saw them, because I hadn’t come across anybody else whose letters were so warm!” In person, they were everything she hoped they be. There was something about them that Sierra found reassuring; she had found a family for her baby.

By the time the legal work was done, Sierra had completed her junior year of high school, received the highest GPA she’d ever received (“It’s really helpful when you don’t have a social life.”), and had gotten back together with Colin. He had told her that he regretted the decision he made and that he loved herand she was still in love with him.

On the morning of August 6, 2004, Sierra’s water broke. On the way to the hospital, she had specific instructions for her father: “Bring me a pizza for when I’m done.” Sierra had thought that she’d have a natural birth. “My mom and I had watched birthing videos, which by the way is a terrible idea if you’re pregnant, don’t do it. Anyway, I didn’t want an epidural.” But there were some complications during labor because of her age and, four hours into it, she changed her mind. “It made me feel really strange and drunk and drowsy. It literally made me see stars,” she said.  

The baby, a girl named Catie, was born as at 4:00 a.m the next day. She weighed 7 and a half pounds. Gibby and John had flown in for the birth. Colin came to visit as well. “I have a distinct memory of knowing that everything was going to be alright. At which point I was like, O.K., where is my pizza?” Sierra said, laughing.

There was a moment, though, when she was holding Catie at the hospital and Colin gave them both a hug when she thought “Wow, this could this could be my little family, but I’m deciding not to do this.” She started crying. “That was a weird feeling,” she said. But ultimately, she knew she had made the right decision. “I didn’t feel regret, it was just a thought that, if things had been different this could have been it for me. But things weren’t different.”

“If things had been different this could have been it for me. But things weren’t different.”

Sierra was discharged from the hospital a few days shy of her 16th birthday, and then Catie left for California with Gibby and John. “I was happy to go back to being a kid…doing stupid crap like going to dances..doing the stuff that I was supposed to be focusing on in the first place,” she said.  

A few months later, when Sierra started her senior year, things had changed, and so had she. The experience in the past year had made her realize what was important to her and that she didn’t want to be the “reckless and irresponsible” person she had been. She broke up with Colin and focused on keeping her grades up, applying to college, and ignoring all the gossip about her. “I was the girl who had had a baby, and that ended up following me for a while.” She attended a college in Maryland where there were students from her high school. “The news spread pretty quickly,” she said. “I didn’t mind talking about it if someone asked me, but I didn’t like people gossiping about it behind my back.” In fact, when Sierra told her now-husband, Ben, who she met in college, about Catie, he told her he already knew. (“He didn’t blink an eye!” Sierra said.)

When Catie was 3, Gibby and John moved to Virginia, bringing them much closer to Sierra and her family. They’ve been open with Catie about everything since the beginning. “She’s always understood the relationship between us, she even has a picture of me in her room!” Sierra said. Being closer in proximity made it easier for her and Catie to see one another every few months. 

When Sierra and Ben got married, in 2015, Catie, who was 11 at the time, served as an honorary bridesmaid. They see one another at family dinners, holidays, and birthdays. “We don’t see one another as often as I’d like, but I’m around for the important things. I went to a horse show of hers this past weekend. It was nice to see her nerding out over something she’s passionate about,” she said.


Sierra at her wedding, in 2015.

It’s been nearly 13 years since Sierra had Catie, and now she’s pregnant again. This time, it was planned. She and Ben have been together for nine years. “When things were getting serious, I told him if he planned on sticking around he should get used to the idea of a house full of babies and animals. He didn’t go running. So, really, it was a match made in heaven,” she said.

Sierra went off her birth control in December and got pregnant shortly after. “It’s been really interesting this time around. You know, being an adult and being pregnant,” she said. “I’m still definitely intimidated. It’s a huge undertaking to take care of another person and have them 100 percent dependent on you. But it’s also an awesome feeling.”

When I asked her how she felt about having a baby again, she laughed. “I’m excited. A little nervous. But excited. Very, very excited. I’m ready for it.”

*Name has been changed.