Nearly three decades after they became close friends while skateboarding in Indianapolis, three men who grew up without fathers in their daily lives are grappling with the idea of becoming dads themselves.

“There is a fear there,” Lucy Chandler said of her husband, Lamont, as she sat drinking a root beer at the Sinking Ship, a bar not far from the home they share in Indianapolis.

At the time, Ms. Chandler was six months pregnant.

“For one thing, he is his dad’s son,” she said. “He was a terrible father and not there for his mother at all. Knowing that makes him think: ‘Do I have this in me? Am I going to be like this if something happens?’”

Mr. Chandler, 42, didn’t disagree.

“Do I feel like that could be part of me?” he said. “All the time. Totally. What if the DNA is in me? I have to be better.”

When Lamont was a teenager, his mother believed he should have a relationship with his father and began sending him to his house occasionally on weekends. It didn’t help. His father worked nights, so he would often sleep during the time he was supposed to bond with his son.

By that time, Mr. Chandler was seriously into skateboarding. Having gotten his first board at age 12, a Powell Peralta Lance Mountain, he took to the sport immediately. Unlike other physical endeavors, it was something he could do alone or with friends. It also attracted like-minded kids who embraced the idea of being outsiders, like Tim Cullinan, now a bartender in Indianapolis, and Lee Fennimore, who creates marketing materials for real estate brokers in New York.

“All that anger and sadness and those things, I think riding with my friends gave me something to be positive about,” Mr. Chandler said. “It let me say: ‘O.K., I’m not going to have this perfect dad, but I’ve got the support of my crew. I’ve got my boys here with me, and they love me.’”

Things with his father never got better. While Mr. Chandler attended Ball State University in Muncie, Ind., his father stopped providing the financial assistance that helped pay for tuition. When his father tried to reconnect over dinner in 2003, the younger Mr. Chandler decided it was too late. It would be the last time he would see his father alive.

In 2013, he received word that his father had died. Reluctantly, he went to the funeral with his mother.

“When I first got the call, I thought: ‘Man, it’s the worst. I messed up and I should have reached out,’” Mr. Chandler said. “But there was not ever anything to miss with my dad. At the funeral, I felt bad that I didn’t feel that bad.”

By then, Mr. Chandler, who runs his own advertising business, had already met his future wife, a paralegal who specializes in divorces and family law. Early in their relationship, he believed she was the one he was going to marry. He even asked whether she wanted children. Last year, they began trying.

“We’ve had some really rough patches over the last few months,” Ms. Chandler, 35, said. “But it comes back to him insisting on being there and being the dad. That is the focus. We are having a child. I am scared and ask myself, ‘Am I going to be a good mom?’ But I have a great mom. I have a great dad. I have a good place that I am coming from.”

By Ms. Chandler’s account, her husband’s attitude toward the pregnancy has bordered on rabid. He buys shoes for the baby — it’s going to be a boy — whenever he can. He decorated the nursery. He attends classes both with his wife and on his own, and goes to every doctor’s appointment.

“I have to connect myself even more,” Mr. Chandler said. “I have a fear of not being connected, of suddenly wanting to bolt. The fear of saying, ‘See you later.’”

In some ways, Mr. Chandler had a harder time than the two friends he skated with all those years ago. Mr. Cullinan, 43, was 12 years old the last time he saw his father, a command sergeant major in the Army who had long been estranged from the family.

Mr. Cullinan remembered that he was playing outside with a few other boys when his father and a friend pulled up in a car. His father didn’t bother getting out when he said he was headed for the airport. The two ended up never speaking again, although they exchanged a few emails more than 10 years ago. When his father died in 2009, the obituary listed his children from his new family, but not Tim or his two siblings.

Mr. Cullinan’s mother bought him his first skateboard — a Vision John Grigley Mini — when he was in eighth grade, and a new life, with new friends, opened up for him.

Almost nine years ago, Mr. Cullinan began dating Celeste Napoli. When they got together, her daughter, Beatrice, was a baby, whose father was gone. Over the course of a decade, Mr. Cullinan and Ms. Napoli have had tumultuous periods, breaking up for months at a time. One included an extended time during which he sold almost everything he owned, including his car, and moved to New York. After three weeks, he had decided to fly back to Indianapolis for Beatrice’s sixth birthday party. He and Ms. Napoli moved back in together within the year.

“If Beatrice wasn’t in the picture, it would have been easier if we had broken up and then just let that go,” Mr. Cullinan said. “So, yeah, she has played a big part in me staying, us working through things.

“Sometimes I think it has something to do with not having a dad,” Mr. Cullinan continued. “When we have broken up, I’ve thought how terrible it would be like to leave Beatrice as well.”

Mr. Cullinan is the only father Beatrice has known. But she calls him Timmy. He defers to Ms. Napoli, who works as a social worker for the state, on disciplinary issues. And even though he has gotten used to the routines of parenthood and plans to marry Ms. Napoli, he is unwilling to have a child with her, despite her wishes.

“I’m older, and I don’t want to be that dude that is chasing a little kid around when I’m 50,” Mr. Cullinan said. “I don’t want to have my first kid now. I’m almost 44. The timing on that is just not good. I can say that all day long, and Celeste would still be like, ‘No time like the present.’ And I say, ‘No, that window is closed.’”

His friend Mr. Fennimore’s experience, or nonexperience, with his father goes even deeper. Mr. Fennimore has only vague memories to go along with a few photos of the man at his christening. He barely remembers the last time he saw him. It was in grade school. It may have involved a long drive from Indianapolis to Dayton, Ohio.

“Some of my friends or girlfriends ask me, ‘Don’t you miss him and want to know who he is?’” Mr. Fennimore, 41, said. “Why? I didn’t know who he was then, so why would I care now? My entire life has been me and my mom.”

As with his friends, Mr. Fennimore began skateboarding in his early teens. His first board was a Tony Hawk, and skating soon became his identity. The popular kids in high school would make fun of him and his friends for being skater rats, but they just didn’t care. And when Mr. Fennimore went to Indiana University in Bloomington, the same cheerleaders who had looked down on him in high school suddenly found his self-assurance appealing.

After college, he had a series of relationships, three of which lasted more than four years. The last ended because the woman he was seeing wanted to have children and he was cool to the idea. It wasn’t that he was totally against it, he said. But having never known what it means to have a father, he has not felt the need to become one.

“If there was a time to do it, it definitely has to happen in the next year or two,” Mr. Fennimore said. “I could have a kid. I could be a good dad. Or I could not have a kid and wouldn’t feel unfulfilled.

“For me, I’m comfortable dying tomorrow. I’ve lived the life that I wanted. But then I’m on a plane and hit turbulence and I think, ‘I don’t want to die!’ It’s good to tell yourself, ‘Yeah, I’m fine not having kids.’ Then, when you are faced with ‘I’m going to die tomorrow,’ you think, ‘I haven’t done anything.’”

Mr. Chandler, who continues his countdown to fatherhood, has already told his wife that he wants two children so that their son won’t be spoiled. And he is elated with the idea of giving his son the life he never had.

“I want to be there to help him learn and experience the world,” Mr. Chandler said. “I just got into camping a couple of years ago. I want to take him camping. I want to teach him how to bike and read and get excited for little victories. In a way, I’m living through my kid.

“It’s like skateboarding,” he continued. “You don’t just go and say, ‘I just did this crazy trick on the first try.’ Likewise, with the kid, I’ll make mistakes along the way. The attempt is better than not trying it at all. You learn from the fall.”