5 Ways To Raise an Awesome Son if You’re a Single Mom (With No Regrets)

As my second child turns 18 this month, I can’t help reflecting on how much he’s grown over the years. Or the many obstacles we have overcome.

Gazing at the young man before me, I am proud. Despite all the challenges and strikes against him, he’s on his way.

Most years, it wasn’t easy. I have to wonder, How did it work out so well despite my many — admittedly — parenting mistakes and personal weaknesses?

For single moms in the same predicament as me, I have some encouraging words for you: There is, most definitely, light at the end of the tunnel — even if you seem to have days on end of not seeing even a tiny glimmer of it.

Here are some tips on raising a mature, resilient, confident, strong, brave, happy, smart, friendly, healthy, and kind young man. These are all characteristics of my son — many people tell me so; it’s just not mommy bias speaking here — and they can be your son’s, too.

A single mom’s many roles

Being a mom involves the usual — all of which you know well: chef, dishwasher, breast feeder, diaper changer, grape cutter, ball chaser, sandwich slicer, cookie maker, sock mender, nurse, shopper, birthday party host, reader, playground swinger, chauffeur, playdate organizer, entertainment center, counselor, and judge.

Not necessarily in that order.

As a homeschooler, I added teacher to the list. It wasn’t that I was a glutton for punishment or that I had invincible superpowers that allowed me to do it all. I firmly believed homeschooling was the best way to educate my children. (If you’d like to hear more about our homeschooling years, check out my articles like 3 Back to School Essentials for Successful Homeschooling.)

When Latif was 4 and I became a single mom, I added father figure and male role model to the ever-expanding list of mom roles. Unfortunately, I was wading into terrain where I had no playbook. These new roles were daunting to say the least. But, as I soon realized, they are among the most critical components in raising a son well.

At the time — 2006 — there weren’t any books or websites that offered help to single moms without religious principles attached. In fact, I felt like a social pariah, frowned upon by the religious folks I knew, for my choice. (And unfortunately, today, that is still basically true.) I was looking for a simple guidebook like Perfect Single Parenting of Boys in 10 Steps, but found nothing.

Left to my own devices, I adopted — and adapted — some good general parenting advice while I was still in the thick of it. Learning by doing was my motto. I also relied on my gut feelings and mother’s intuition to carry me through. They both steered me well during numerous hard times. I urge you to tap into yours. It takes practice to know what to listen for, but once it clicks for you, parenting will become much easier.

Here’s what I discovered to work the best as a single mom when raising a son.

1. Learn all about boys from the experts

Books are a major part of our lives — for me as a writer and for my children as homeschoolers. But all books aren’t equally good. Here are a few gems packed with tons of ideas and insights on nurturing boys to become extraordinary men.

I prefer to borrow books from the library and own very few myself. But these I found so invaluable that I bought my own copies. Now, they are dog-eared, stained, and filled with handwritten margin notes and underlines (with a few pencil and crayon “scribbles” from my kiddos mimicking their bookish mommy).

Note: Links here go to enlightening and educational reviews or interviews with the authors about their books.

• The Wonder of Boys: What Parents, Mentors and Educators Can Do to Shape Boys into Exceptional Men by David Gurian. This book came out a decade before I became a single mom of two boys, but its evergreen content is timeless. It was truly a lifesaver then…as it still is as I navigate the later teen years with them. Gurian has written several other excellent books focusing on education and children. Highly recommend!
• The sequel to the previous title by the same author is as well-written, researched, and informative. A Fine Young Man: What Parents, Mentors and Educators Can Do to Shape Adolescent Boys Into Exceptional Men. I find myself rereading large chunks of this one as situations arise (almost daily) and I’m desperate for guidance and advice.
• Raising Cain: Protecting the Emotional Lives of Boys by Dan Kindlon and Michael Thompson is a classic on raising boys. What I most like about this book is its emphasis on nurturing boys’ emotive sides. In a society in which males get the message “to tough it up” and that crying is girlish, a book actually showing you how to counter that is invaluable when you’re raising boys.
• Masterminds & Wingmen: Helping Our Boys Cope with Schoolyard Power, Locker-Room Tests, Girlfriends, and the New Rules of Boy World by Rosalind Wiseman. Any parent — mom or dad — with a male tween or teen needs to read this perceptive book. It is loaded with insights on the inner lives and thought processes of male tweens and teenagers that will open your eyes to seeing your son in a whole new way. The tips on dealing with bullies are unmatched. The I promise/He promises contract is something that works. I keep this one close at all times.
• The Mama’s Boy Myth: Why Keeping Our Sons Close Makes Them Stronger by Kate Stone Lombardi. Kudos to this author for finally putting to rest the myth that a close mother-son relationship creates a weak, effeminate man. To the contrary, when nurturing a tight bond with their sons, moms build empathetic men inclined to negotiation and compromise rather than strong-man, iron fist tactics. Who doesn’t want that? Your future daughter- or son-in-law and your future grandchildren will thank you!

2. Encourage dad to be involved in your son’s life

The importance of a father in a son’s life is without question. If at all possible, encourage your child’s dad to take an active role in his life. If you’re the custodial parent, be more than willing to suggest or agree to activities with his father, even ones that aren’t scheduled on his regular court-ordered weekends.

Sadly, not all dads deserve to be with their sons.

Courts today do not recognize emotional abuse as a reason to limit or withhold visits as they do in cases of documented physical or sexual abuse. In my case, it was difficult to release my children to my ex-husband every other weekend knowing that they’d be called hurtful names, ridiculed, and humiliated. (Based on reports from my children and on past experiences from when we were married.)

As a result, I made sure that I was mentally prepared every time to be emotionally available and sympathetic to my kids when they returned. All I could do was listen attentively while they described the details of their negative experiences. Often this didn’t come out all at once. More likely, it was over hours, days, or even weeks. Sometimes, if triggered, it could appear months or even years later.

I countered all the hurt with positive reinforcement to boost their injured self-image. I let them know that they were loved and wanted in my home. Inside, I was seething in anger directed at my ex-husband.

However, knowing that they looked up to their father as their first male role model, I kept my personal animosities toward him to myself. I knew that criticizing their dad would be internalized by my boys into self-hate, in as much as my sons identified with him. I didn’t want or need that.

As Latif got older, the father-son bond became totally unraveled. His father refused to take him anymore for weekend visits, claiming Latif was “disrespectful.” I never received a clear explanation from my ex-husband on what that meant or why it warranted a complete end to all visits. From what I could gather, it had a lot to do with Latif’s unwillingness to recite Koranic prayers or write them in Arabic.

In response, I searched out male friends and neighbors to meet Latif’s need for father figures.

3. Identify male role models to be active in your son’s life

I am fortunate to have people around me who take a genuine interest in my son’s well-being. But it was by design, not accident.

Friends’ dads

As a single mom, I’d take my children to local playgrounds, parks and libraries often. I’d strike up conversations easily with other parents — both moms and dads. When our kids played well together, we’d begin to spend time at each other’s houses. In this way, my children benefited from activities in which their friends’ fathers participated. Usually this was sports-related.

My childhood male friend

Latif also got to experience a father figure from time spent with a male childhood friend who’d take us out on day trips at a state or an amusement park. I was grateful for my friend’s interest in doing what he could to give a “normal” childhood to my kids. Although my children may have preferred that both of their biological parents to have been the ones with them on these outings, they had a great time with my old friend as their dad-substitute for the day.

Neighbors

I was fortunate to have a neighbor who was a single dad with a son the same age as Latif. All of them enjoyed sports. Along with Latif’s younger brother, they’d play flag football and soccer together on weekend afternoons with even teams. They’d also enjoy sleepovers at their friend’s house.

When Latif was a teenager, he naturally became the “big brother” to three other boys (+ one little girl) of single parents in our neighborhood. He served as coach, teaching them how to pitch a baseball or punt a football. The little ones clearly looked up to him and loved being around Latif.

This experience taught me that my efforts to create effective male role models for Latif had paid off! One day, I believe Latif will be a dad who takes an active role in his own children’s lives, just as he did for many neighbors of single parents.

Boy Scouts

I enrolled my sons in Boy Scouts when they were young in the hopes of building relationships that would last. Several dads “adopted” my sons, including them in scouting activities like hiking, sledding, and boating right beside their own sons.

Club members

Latif loves following sports of all types at both the college and professional levels. Unsurprisingly, so did many of the male members at our local athletic club. Latif is a great conversationalist and so had no problem discussing all things sports with them. Later, they’d tell me how impressed they were with his knowledge and understanding of sports. They confirmed he was wiser than his years. Latif looked forward to meeting up with his “sports pals” two or three times per week and talking over the latest scores, big plays, and upcoming sports events.

Coaches

Latif also loves to play sports. So I enrolled him in all sorts of rec sports including soccer, lacrosse and rugby. We could never afford travel teams yet Latif’s natural ability shone through in all cases. He developed great working relationships with all his coaches over the years. Many complimented him on his ability to look ahead, strategy-wise, and lead his team on to winning. All this despite his lack of intensive playing time like his teammates had had on travel teams.

Now at 18, he’s hopeful that there will be a lacrosse season in the spring during the Age of Covid. He lives for any and all occasions to hit the field and scrimmage or practice technique. I do what I can to make these meetups happen, knowing how he thrives on them.

Teachers

As a senior in high school, Latif also develops close relationships with many male teachers and coaches and even with his principal. He’s a likable person who’s very sociable. He also has a broad knowledge base from so much homeschool reading. These two factors make Latif very easy to talk to. After school times and activities provide ample opportunities for these relationship-building experiences to happen regularly.

TIP: Tap into the male friends and neighbors around you to mentor your son. Maybe you’re lucky enough — unlike me — to have a brother, brother-in-law, father, or uncle who’d be happy to get involved in your son’s life. Big Brother programs are an option, too. What about a community center or house of worship? Leave no stone unturned when it comes to raising your son.

Of course, don’t let a total stranger spend time with your son, especially alone. Even neighbors and acquaintances may be questionable. Spend time getting to know potential father figures before allowing any outings when you’re not participating. Better to be safe than sorry.

4. Help him find and stay with his tribe

Like most boys, Latif loves to be doing something active all the time. Currently, he thinks of himself as a varsity lax player. A team member. Playing the game he loves so much with his tribe of teammates is what he lives for.

So, I’m there on the sidelines cheering him on. (He says I’m embarrassing him.) Giving him the independence to carve his own path in the world and forge lasting friendships. I certainly don’t need to, but I encourage him to practice and learn all he can.

What does your son love to do most of all? If he doesn’t know yet, encourage him to try different things. Sports is popular with many boys, but not all. Music? Martial arts? Robotics? Coding? Woodworking? The possibilities are endless! Foster a sense of belonging in your son by assisting him to find his tribe. He will be happy & healthy — what all parents aspire to for their kids. As a result, you will be, too.

5. Let your son be a child or teenager (not “the man of the house”)

Single moms may have a tendency to lean on their older son as “the man of the house.” They may confide in him with their problems as if their son were their partner or best friend. Avoid doing this.

Growing up is tough enough without added responsibilities that you force on him. Feeling like he has to meet your expectations or he’ll lose your love is a horrible place to be in. That, for instance, he “should” be able to fix the car or pay the bills. That’s a tall order for someone navigating the challenges and changes that naturally come with adolescence.

Allow him to be a teenager.

Remember that you are supposed to be helping him. Not the other way around.

Possibly one day, when your son is much older and no longer living with you, you may become “friends.” You may confide in him about your problems or tell him some of your most private thoughts. You may even tell him why you divorced his father many years ago.

At this point, I can’t see myself ever doing these things. I do envision my place in his life as a constant source of encouragement and as a confidante — if he seeks my opinion concerning a major life decision, for example. I’ll gladly share my experiences and knowledge as a supportive parent.

For now, Latif is my older son in the house, but not “the man of the house.” He has chores and age-appropriate responsibilities, both of which are important for building character and instilling the value of structure and discipline. But no obligations that an adult should handle. And we prefer to keep it that way.

Conclusions about raising a son when you’re a single mom

Latif and I both have come far over the last 18 years. It hasn’t been all fun and games, but most of it has. As a single mom, I made a point to do certain things in my parenting to fulfill my son’s need for a father figure. Doing so has shaped him into becoming the remarkable young man he is today.

For me, I consistently followed through using these five guiding principles. Seeking out opportunities to fulfill his need to have other boys or male role models in his life is crucial to his (and your) success:

1. Learning all I could about boys from experts and acting on their advice about raising boys
2. Encouraging my son’s relationship with his father (until it became too toxic)
3. Identifying male friends to mentor my son in various ways
4. Helping my son find his tribe and doing things to promote their unity
5. Allowing my son to enjoy childhood and adolescence without the unfair demands of being the “man of the house.”

Raising boys is a lot of work. There may be difficult days when you feel like giving up. Don’t despair — even if you feel like the world’s against you and doesn’t care. Be proactive and ask for help when needed. The years will fly by even though some days may seem like an eternity. Then one day before you know it, you’ll see a young man with a bright future standing before you (and probably taller than you, too). And that will be a well-earned accomplishment. Job well done, mom!