The $15 Gift That Taught Me a $50 Lesson

A true story of generosity and overthinking.

Bob Olson is the host of Afterlife TV, the author of Answers About The Afterlife, Insight from Hindsight, and The Magic Mala, and the founder of BestPsychicDirectory.com.

Photo by Joshua Lam on Unsplash

Last week’s story about A Spirit Guide Named Momo was quite a journey, so this week, I’m excited to share a shorter piece that’s perfect for getting into the holiday spirit! I received a lot of positive feedback on the Momo story, so if you haven’t read it yet, many people say it’s worth your time. The most common feedback I received was, “I couldn’t stop reading, and when it ended, I felt sad that it was over.”

If you’re like me, you probably still need to purchase a few last-minute holiday gifts. Below is a true story that, while somewhat embarrassing, illustrates the dysfunctional spiral people can find themselves in when trying to find the perfect gift.

This story took place nearly twenty years ago, and I hope I learned a valuable lesson from it. But time will tell, as I’m not finished my holiday shopping yet.

What to Avoid When Buying a Gift This Holiday Season

A few years ago, our friends Michael and Cheryl invited my wife, Melissa, and me to attend a barbecue on a boat. Well, this wasn’t just any boat. Michael’s parents had chartered a 157-foot yacht with four floors and a crew of ten people.

This was all very exciting, as Melissa and I had never been on a yacht of any length. Since we’d only met Michael’s parents briefly in the past, we also looked forward to spending some time with them.

Two days before the barbecue, I had the idea to bring Michael’s dad one of my favorite cigars. I’m an occasional cigar smoker, and I was recently given the absolute best cigar I’d ever smoked. Consequently, I had this heart-centered desire to share my recent find with Michael’s father.

I usually smoke a nice little cigar named La Gloria Cubana, which costs only $6 at my barbershop. But when some close friends gave me a birthday gift, they got me a cigar named La Aurora. Once I smoked it, this new $15 cigar suddenly made my $6 cigar taste like dirt. I now had a new favorite cigar that I could get for special occasions, and attending a barbecue on a yacht seemed like the perfect occasion.

Suddenly, I realized that I couldn’t give Michael’s father a gift of appreciation without giving his mother something, too. I asked Melissa what we should get his mother for a gift, and she quickly responded, “Well, if you’re giving him your favorite cigar, I’ll give her my favorite tea.”

Great, problem solved. No, wait, it occurred to me that they might not like cigars or tea. I had to call our friends to find out.

“…And we wanted to show our appreciation to Michael’s parents for inviting us, so I wondered if his dad likes cigars,” I asked Cheryl by phone.

“Oh yes, that’s a wonderful gift. He doesn’t smoke them often, but he loves an occasional cigar. That’s really nice of you. He’ll be thrilled,” she responded.

Hmm, Cheryl’s enthusiasm was delivered with a much higher octane than I anticipated. After all, I was only giving the man one little cigar, a simple gesture of appreciation.

I wondered, Did she think I intended to give him an entire box of cigars? Let’s see, 24 times $15… Oh God, I hope not.

I had to water down Cheryl’s expectations in case I had given her the wrong impression.

“Now, don’t get me wrong. I’m only giving him a couple of cigars. (One sounded cheap as I was saying it to her, so one cigar grew to two cigars.) It’s just a gesture of appreciation. And how about Michael’s mom? Does she drink tea?”

“She loves tea. That’s a perfect gift,” said Cheryl.

Fantastic, I had a plan. The next day, I went to my barbershop to buy two of my favorite cigars. As I drove there, however, I realized that I needed something to put the cigars in, a nice container of some sort. I couldn’t merely hand the man two cigars. That would be uncivilized.

When I arrived at the barbershop, I learned there was no cheap way to package the cigars. They did have some nice leather cigar holders, with an average price of $30.

Oh geez, I thought. I set out to give a simple $15 cigar, which has turned into two cigars and a leather case. No, I can’t do it. This is getting ridiculous.

Then my barber mentioned that cigar cases were on sale for half price.

Half price, huh? I’ll get it and be done with it, I thought to myself.

That’s when I noticed that cigar holders are for either one cigar or three—nothing for just two. Surely, I can’t put only two cigars in a three-cigar case. That would look foolish. I decided to get three cigars and the leather case.

Just as I grabbed three La Auroras from the humidor, I realized Michael’s father might want to smoke one with me. That presented a new problem. I certainly couldn’t smoke one of the cigars I just gave him. I grabbed a fourth to enjoy a cigar with Michael’s dad on the yacht without smoking one of his gifts.

Okay, this is going to be perfect, I thought to myself.

Melissa walked into the shop as the barber rang up my items on the register. She’d been waiting for me in the car, wondering what was taking so long. She saw me purchasing four cigars and a leather case.

“I thought you came here to buy one cigar?” she asked. Of course, she knew me well, so she wasn’t that surprised.

“Well, after talking with Cheryl, I decided to give him two. But then I wanted something to put them in, and all they have are these cases. However, the cases are for either one cigar or three, and I can’t give him two cigars in a three-cigar case. That would be silly. Plus, I had to get one cigar for myself just in case Michael’s dad wants to smoke one with me, as I can’t smoke one of the cigars I just gave him.”

Melissa looked at me like I was nuts, then looked at the case and cigars I was buying. “Those are fat cigars. Are you sure they’ll fit in that case?”

My barber and I looked at one another, befuddled.

I opened the leather case to find the cigars didn’t fit. They were too fat. The cigars were thin and pointed at each end but extra thick in the middle. Melissa and I proceeded to try every case in the barbershop. The cigars wouldn’t fit any of them. I paid for the cigars and left without a case.

“What a bummer, and they were having a half-off sale, too,” I said as we got into the car. “I’m going to the cigar shop down the street.”

Melissa knew I was now on a mission, and interfering was pointless.

“I’ll walk across the street to get a box of my favorite tea,” she said. “I’ll meet you back at the car.” She didn’t want any part of the predicament I’d created for myself.

When I entered the cigar shop, I had one of the cigars in my pocket. I explained my plight to the bored teenage clerk, and he was only too happy to pull out all their cigar holders from the glass display. After fifteen minutes of searching, he found one leather cigar case that worked. It was for three cigars but would only hold two of the fat cigars I’d purchased. And it was 30 bucks—no half-off sale. I no longer cared. I’d have paid twice that amount just to be done with it.

As I stood at the counter paying for the cigar case, it occurred to me that Michael’s father might not own a cigar cutter or at least might not have one with him.

How is he going to cut the cigars on the yacht? I wondered.

I looked at all the nice cigar cutters on the counter, averaging $30. Then I imagined Melissa’s expression if I bought one. I could almost hear her asking (sarcastically), “What, no lighter?” I caught hold of myself, bought a cheap cutter for three bucks, and grabbed a book of matches.

Two days later, we went to the barbecue. The yacht was fantastic, and the feast included some of the most scrumptious steak and lobster I’d ever tasted. Michael’s dad seemed to like the cigars and leather case I gave him. Unfortunately, it was raining outside, so we didn’t have a smoke together.

At one point during the day, Michael’s father approached me and gave me two of his favorite cigars. I learned from the Internet that his favorite cigar costs $50.

Oh great, I thought. My $15 cigars are going to taste like dirt to him.

Happy holidays to you and yours!
With love, Bob & Melissa
♥️🎄🎁

PS, I share this story in honor of Michael’s beloved father and Cheryl’s second dad, who is being cared for by hospice this holiday season. May his transition be peaceful and loving, and may Michael, Cheryl, and their family members be surrounded by love and support this Christmas.

Cheryl wrote a beautiful blog this week that I recommend reading. She elegantly captured the dichotomy of feelings one has during the holidays as a loved one prepares for their journey home.

Speaking of gift buying: This story was featured in my newest book, Insight From Hindsight, which makes an excellent gift for anyone who loves engaging stories that end with life lessons.

Bob Olson is the host of Afterlife TV, the author of Answers about the Afterlife, Insight from Hindsight, and The Magic Mala, and the creator of the most trusted directory of psychics, mediums, animal communicators, and energy healers, BestPsychicDirectory.com.