Anthony Woolever never expected to become an expert on raising daughters. Today, however, he and his wife Jennifer are raising five girls ranging from a newborn to young adulthood, along with one son.
Their blended family spans nearly two decades in age, creating a parenting journey unlike anything Anthony imagined when he first became a father.
Looking back, he can pinpoint the moment everything changed.
“As soon as she was born, my heart immediately softened,” Anthony said of his first daughter. “That was the first crack in my shell.”
Before fatherhood, Anthony’s life had been shaped by adversity, military service and a disciplined approach to nearly everything he did. Emotions were often pushed aside in favor of responsibility and structure.
Seeing life through a new lens
Holding his daughter for the first time forced him to see life through a different lens.
“It made me realize the importance of being gentle and loving with her,” he said.
That lesson has remained at the center of his parenting philosophy ever since.
Anthony’s family story is anything but traditional. Three of his daughters came into his life when he married Jennifer. Two children came from his previous marriage. Then, after believing their family had reached its final chapter, the couple welcomed baby Julia into the world.
The result is a household where conversations can shift from college internships to diapers in a matter of minutes.
“It’s definitely an adjustment,” Anthony said. “When all of your children are beyond their toddler years, your house becomes an anti-baby house. Then suddenly you have a baby again.”
From teens to a toddler
While the logistics of raising children at vastly different stages of life can be challenging, Anthony believes the fundamentals of fatherhood remain the same. Whether he is talking with a college student, a teenager or a toddler, his goal is to be fully present and engaged.
That commitment became especially important when he stepped into the role of father figure for Jennifer’s daughters. The girls had experienced instability and lacked strong male role models in their lives. Building trust would take time.
“There were adjusting periods,” Anthony acknowledged.
Rather than trying to force relationships, he focused on consistency. He wanted the girls to see what fatherhood looked like in practice. Even when his biological children were living elsewhere, he made sure to connect with them every day.
“No matter what, if they called, I answered the phone,” he said. “I connected with them every single day.”
Over time, the girls noticed. They saw a man who kept his word, showed up consistently and remained involved even when life became complicated.
“They got to see that being a dad isn’t easy,” Anthony said. “But, it also doesn’t have to be the most complicated thing in the world.”
Girls need to hear from dads frequently
One of the most significant turning points came during a personal retreat several years ago. Anthony realized there was something his bonus daughters needed to hear from him, something he had been reluctant to say because he wasn’t sure where the boundaries should be.
“It was revealed to me that they needed to hear ‘I love you’ as well,” he said.
From that day forward, he made a commitment.
“There’s not been a night that I’ve not told them I love them,” he said. “When they’re physically available, I hug them and tell them I love them.”
The impact surprised even him.
“They became different,” Anthony said. “They were great girls before, but it’s made all the difference in the world.”
Daily affirmation
For Anthony, that experience reinforced an important truth. Daughters need more than financial support, transportation and occasional advice. They need affirmation. They need to know they are loved and valued by the men who matter most in their lives.
That belief influences nearly every aspect of his parenting today. Whether discussing college plans, friendships, dating relationships or future careers, Anthony wants his daughters to know their worth is rooted in who they are rather than what they accomplish.
“We tell the girls we’re proud of them, but we specify why,” he said. “We’re proud of their effort, character and the decisions they make.”
Teach girls critical thinking skills
Those conversations often lead to one of Anthony’s favorite topics: critical thinking.
“How to think, not what to think,” he said. “That’s one of the most important things girl dads can teach our kids.”
Rather than demanding agreement, Anthony encourages questions. The Woolever household regularly discusses finances, politics, faith, relationships and current events. His daughters are free to challenge ideas, express opinions and develop their own viewpoints.
“There are plenty of things I’m teaching you today that you’re going to disagree with me on, and that’s okay,” he tells them.
What matters is learning how to evaluate information and make wise decisions. Anthony believes that skill will serve his daughters far better than simply following the crowd.
Encourage independence
That same philosophy shapes how he prepares them for adulthood. He encourages independence by allowing his daughters to solve problems themselves whenever possible.
They make phone calls, research opportunities, negotiate purchases and explore career paths with guidance rather than rescue.
“I’ll often do the research and find the important people to talk to,” he said. “But, I won’t make the phone calls for them.”
His daughters have responded well to the challenge. One pursued job-shadowing opportunities with legal professionals. Another secured internships while still in college. Their successes have reinforced Anthony’s belief that confidence grows when parents allow children to take ownership of their decisions.
Listen without solving
Like most fathers, however, Anthony admits there are areas where he still struggles. Listening is one of them.
“This was, hands down, the thing I struggle the most with,” he admitted.
His instinct is to solve problems. When daughters bring frustrations to him, he naturally wants to fix the situation and move forward. Over time, however, he has learned that daughters often need understanding before they need solutions.
“Sometimes they just don’t want to hear that,” he said.
Learning to listen without immediately taking control remains a work in progress. Yet, it has become one of the most valuable lessons of his parenting journey.
Guiding principles
As Anthony reflects on raising daughters, he doesn’t point to complicated strategies or groundbreaking techniques. Instead, he returns to a handful of simple principles that have guided him through every season of fatherhood:
- Take an interest in their lives.
- Show up consistently.
- Teach them how to think.
- Encourage independence.
- Tell them you love them.
- Then do it again tomorrow.
“A lot of guys hear that and think saying it is enough,” Anthony said. “No. Say it, show it, live it.”
For a father raising five daughters, those words aren’t just advice. They are a daily commitment.
For more information
People can connect with Anthony on these platforms:
- Website = https://anthonywoolever.substack.com
- Facebook = www.facebook.com/eaw2001
- Instagram = www.instagram.com/anthony.woolever
I am the father of three now-grown young women with families of their own. A native of Wisconsin, I now live in Arizona, but enjoy visiting my eight grandchildren whenever I can.
