4294 Stories - Awaiting Approval:Stories 0; Comments 0.
This site is for Male Haircut Stories and Comments only.

The Grand Challenges by Ben Aldy


My brother and I were blessed with a one wonderful grandfather, my father's dad, or Pappy as we called him. My other granddad had died before we were born, killed in a car wreck.

Pappy had done well in his career in insurance, and he loved sharing his wealth with us in ways that taught us lessons and values which he thought were important. For instance, he gave us each $5 for singing our ABCs, $10 for saying all seven of his "good manners" words, $25 for knowing our 1-12 multiplication tables, $50 for naming the capitals of each state, $75 for performing 30 Marine-style pushups, $100 for reciting all of the books in the Bible in order.... You get the idea. The challenge and the reward grew as we did.

These Grand Challenges, as he called them, came at random, I guess whenever he thought of them. To date, I was the only grandson to have done them all: my brother John had given up on the books of the Bible and my first cousin Paul on, pushups.

Today, Pappy introduced a new challenge, one that Paul and John had already declared they were not doing. I was tempted to say the same, but I didn't want to break my streak. And the reward was a lot of money. I was also smart enough to know that Pappy always wanted what was best for us, and that somehow these all weren't just silly challenges.

Pappy's instructions this time were as follows: Get at least four of the following haircuts and wear each style, groomed neatly, for at least three months before switching to another. The reward: $200! The names of the haircuts, which meant nothing to me, were a burr, a butch, a crewcut, a flattop, an ivy league, and a short back and sides. He also specified that Barber Jim, the old man owner of Jim's Barbershop in our hometown, was to administer each haircut and that we were to be sure to send Pappy a photo of each cut.

School was to start back in two weeks, my ninth grade year, and I knew my dad would soon take my brother and me for our back-to-school haircuts. I would start then. Four haircuts times three months per cut: the haircut challenge would take a full year.

--

We arrived at Jim's Barbershop on the following Saturday morning at about 10 o'clock and by 10:20 I was in the chair, my brother's typical trim already complete. Barber Jim asked me how I wanted my hair cut. I was ready with my sheet of paper listing the cuts. "Which of these is the longest?" I asked and then listed the options Pappy gave me.

Barber Jim pulled his comb out of his white barber smock and began combing through my straight brown hair, as he had many times before. "Well, Ben," he said, "of those you listed, the short back and sides is the longest, but as the name suggests, it is not long. Is that what you want?"

"Yes, please." As he began cutting, I began telling him about my Pappy, his Grand Challenges, and about his latest haircut challenge. He listened attentively, interrupting me only briefly to give instructions, such as "Head down, now."

The cut lasted at most 15 minutes, 14 of which I was turned away from the mirror. When the chair was finally returned to face the mirror, I understood how this haircut got its name. Turning my head to the right side, I saw my left ear fully exposed, a pale white arch of skin shining cleanly above it, at least a half inch wide. A turn to the left revealed the same there.

Barber Jim combed my bangs straight down, until they rest in my line of sight. With his shears, he started cutting them across at my right temple, well above my eyebrow, but then didn't cut them straight across as was customary. Instead, he angled them down, barely cutting off any hair by the time he reached the left side. Holding his comb at an angle above my head, he made a sharp part through my hair on the left side and pulled my bangs back and to the right.

"Ben," he said, with a more serious tone in his voice, "the short back and sides is a very classic haircut that must be styled with hair cream." He reached up on the shelf beside his mirror and pulled down a toothpaste-like box labeled Groom & Clean. "I'll sell you this tube, and you'll need to use it each morning. It should keep your hair neatly in place all day." He squeezed a dab into his hand, rubbed his hands together, and then rubbed his hands through my top hair, tousling it into a mess. He then combed it neatly back into place, my bangs holding firm in a side part like never before.

A hand mirror held behind my head showed the short back and sides from all angles. Barber Jim explained to me the benefit of the tapered back, and added that it's a sign of good barbering, that all gentleman's cuts end in a tapered back. He also said that a cut this close needed to be maintained more often, at least every three weeks.

My dad gave me a big grin and congratulated me on completing the first step of the challenge. He said that I looked real smart. He paid Barber Jim and passed along to me the tube of Groom & Clean. John rolled his eyes at me and said "dork" under his breath.

---

In ninth grade at Macon High School, I was the only guy in my class wearing a proper short back and sides, as evidenced by my school yearbook. Pappy got mailed a copy of my school photo. My best friends Scott, Sarah, and Greg all thought I was crazy for getting my hair cut so short, but Karen liked it, she told me so.

I like it to. Every morning, I washed and dried my hair and styled it with cream, which had the added benefit of making me smell good. Unless it was a day I had gym, I never had to comb it again, and even then, I noticed that I stayed much cooler than my classmates. To my surprise, I never missed my long hair. And I often found myself rubbing the back of my neck because it felt so good.

I kept the short back and sides through three more visits to the barbershop, until the first three months of the haircut challenge were complete. I was now comfortable in this cut, able to style it quickly, and wished I could keep it, but knew that this was not to be. Maybe I would come back to the short back and sides in the end.

---

November 1, 2005

Dear Ben,

Thank you for copy of your school photo. I was glad to see that you accepted my latest challenge. You look great in your short back and sides!

Always take time to look your best. While others may think such is a sign of vanity, I think it is a sign of self-respect.

Love,
Pappy

---

When I revisited the rules of the haircut challenge with Barber Jim on my next visit, he suggested that I had a choice to make as far as my next cut: Do you want to continue going through the haircuts from longest to shortest, or do you want to go the opposite direction--start at the shortest and grow into the others.

While the idea of jumping to the shortest haircut--the burr, according to Jim--really excited me, we ultimately concluded that this would take longer to complete the challenge, as Pappy had made explicit that each haircut must be maintained for three months.

Following this logic, my next style was to be an Ivy League. Barber Jim explained to me the history of the haircut, made famous by rowers at Harvard and Princeton, as he buzzed the back of my head, taking the clippers up and over my crown, where I had never felt the clippers go before. He said this was a distinguishing feature of the cut.

He tapered the sides and back, though not nearly to the extreme as before. He lifted my four inch bangs with his comb and clipped them off, or so it seemed; he really left about an inch and a half. He then proceed to cut the top short, from front to back, first with his clippers over his comb and then with his thinning shears, cutting progressively shorter as he went, so that the longer front blended smoothly with the half-inch long hair at the crown.

When we was finished, rather than reaching for the now familiar Groom & Clean, Jim reached for a small plastic blue-topped jar labeled Krew Komb. He used this to style the front up and to the side. The rest of my hair was pretty much already in place. He showed me my new Ivy League haircut with his hand mirror, noting that it looked like a buzzcut from the back and a short side part from the front. He encouraged me to style the front different ways--to the side, straight up, and straight down--as this is one of the virtues of this convertible cut. I told him I would.

---

My family and friends universally liked the Ivy League cut on me, even my brother John said it looked better than the short back and sides. I liked it, too, though missed rubbing my really short nape or feeling the bare skin over my ears after a fresh cut.

Karen and I are now dating, and she seems to like short haircuts. She always notices when I have been to the barbershop.

I have sent another photo to Pappy.

---

December 15, 2005

Dear Ben,

Thanks for the latest photo. Your ivy league looks sharp! Keep it up and you might be at Harvard one day!

Never be ashamed to be the best groomed man in the room.

I look forward to seeing you and John at Christmas.

Love,
Pappy

---

Pappy came for Christmas. He gave me a dopp kit with my first real razor, and showed me how to use it. He even took me to see Barber Jim, and I learned that they had gone to high school together. Why had this never come up before? Pappy is nearly bald, but Jim buzzed and tapered the little bit that is left.

I am really enjoying the Ivy League haircut. It's so easy to maintain, and I can make it look formal, like the short back and sides, or more casual, depending on how I style it. I usually wear it parted to the side, but sometimes I go a little wild and kind of spike it up. Maybe I am preparing myself for the next cut, a flattop!

---

The three months of Ivy League bliss have passed quickly, and I am back in the chair, somehow more nervous than ever. Does getting a flattop for the first time make everyone nervous? Barber Jim tells me to relax that it's going to look fine.

Minutes later, the cape is covered with the hair that used to be on the back and sides of my head, which I thought was short, but obviously not so much. Jim says he is taking my sides down to a 1-1/2, or 3/16" of an inch. I can't see it yet, but already I feel colder. He cuts the top with clipper over comb and spins me around towards the mirror.

I hold in my gasp when I see the sides of my head in the mirror, which now show equal parts pale white skin and stubble. The top is only slightly shorter than after a fresh ivy league cut.

Barber Jim rubs the now familiar Krew Komb in my top hair and blow drys it up and to attention. Standing behind me with clipper and comb, he positions my head exactly where he wants it and tells me to hold very still. I do.

With eagle eye attention, he flattens the top of my head and squares the sides, returning to the hair dryer twice, followed by a heavy coating of hairspray. Finally, he gives what he calls the "scissor salute," trimming some invisible hairs from the top with shears, the only time they were used during the cut.

Jim shows me the haircut from all angles, showing me the clean skin taper on the sides and back and the "landing strip" of white skin on top. Gulp. He sells me a little pocket brush from a wall display that I have admired for many years, wondering who buys these things, and he tells me that these work well for training the top hair to stand up.

---

Reviews for the flattop are mixed. It's one of those love-it-or-hate-it cuts, with very few people on the fence. Like it or not, everyone wants to touch it, which is ok by me. It feels so good.

Fortunately, Karen loves it. When we kiss, she rubs her hands on the back of my head and massages around my ears with her thumbs. She knows just how to get me excited.

A photo of Karen and me in my flattop has been sent to Pappy. I even tilted my head down a little, so he could see my landing strip.

---

March 25, 2006

Dear Ben,

Haircut #3 and you're looking sharper than ever. Who's this lovely lady on your arm?

Military officers, police men, and firefighters ofter wear flattops. Never forget their service and sacrafice. A good haircut can encourage respect from others, but ultimately you will be judged by your actions.

I am very proud of you.

Love,
Pappy

---

The flattop requires even more maintenance than prior cuts, and I am now regularly going to see Barber Jim every two weeks. Before Easter Sunday, I got it re-cut after only one week because I wanted it to look perfect for the occasion. While the first flattop haircut took a full 40 minutes, Jim can now cut it in about 15. Styling in the morning takes the longest of any cut so far, as I have to blow dry it to get it to stand up right.

---

I am nearing nearly three months since getting my flattop, and I no longer shock myself when I see my reflection. I like the way it looks and feels. Also, adults are nicer to me.

---

"Butch or burr? How short are we going today?" asks Barber Jim.

"I'm thinking burr. I've come this far."

The largest black clippers made, the Oster 76s, are at my forehead. "Ready?" "No." The clippers glide easily across the top of my head, leaving behind a wide path of nearly barren white skin. Stroke after stroke, in rapid succession, the flattop is laid to rest. In a mere minute, my head is devoid of any semblance of hair.

In the mirror, I see the guise of the real me. No long hair to hide behind, no flattop to distract. Just me.

---

It seems odd at the end of every week, with my hair shorter than ever before, to head back into the barbershop to have it shaved again. Every week I get an interesting look from the others in the barbershop when I sit down, almost as if I'm a long-hair that just walked in--a freak of a different kind, I guess. My shower in the morning, water on a bald head, is a totally new sensation--a feeling difficult to describe and certainly indiscernible to those who have always had hair. I haven't used shampoo or a blow dryer in months.

My romance with Karen has gone to a new level, though we've decided not to go all the way just yet. I went to cotillion with her in June. I sent our photo from the dance to Pappy.

---

August 31, 2006

Dear Ben,

Thank you for the photo from the dance. Your navy suit and burr haircut actually go very well together. You look older than 16.

Enclosed find a check for $200 for completing the haircut challenge. Congratulations! When I proposed it, I wasn't sure that any of my grandsons would take me up on my offer, but I hoped you would. I'll be interested to hear what you learned from the experience.

Love,
Pappy

---

September 7, 2006

Dear Pappy,

Thank you for the check for $200. With all the haircuts I had to pay for, I think this may have been a money losing proposition! Ha!

But that's ok, I did learn a lot and appreciate you encouraging me to try so many different short haircuts. I'm actually on haircut #5 now, a regular crewcut. Rest assured, Barber Jim is continuing to keep it neat for me as it grows out. I'm planning to grow it out to the Ivy League, which is shorter than any haircut I would have gotten before the challenge, but will seem long to me now. It's an easy maintenance cut that looked surprisingly good on me. Thanks for showing me this.

From this experience, I have learned to step outside of my comfort zone. It wasn't always easy going back to school with a new haircut, but each time I did and made it through, I felt stronger and realized more and more who I am--and whose opinion really matters.

In the end, it's just hair. I'll enjoy it while I have got it because I may end up losing it like you did. Ha again! And if I do, I already know I look good bald!

Thanks for being an awesome granddad!

Love,
Ben

###



Your Name
Web site designed and hosted by Channel Islands Internet © 2000-2016