5 Life Lessons Told Over 5 Glasses of Wine from a 99-Year Old Filled With Regret

Jordan Gross

“I wish I was more willing to forgive.”

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“There was blood everywhere. But wait, let me backtrack.”

“This piercing voice was screaming so loudly that I could hear her from the second floor. She lives on the fourth. I’m a nurse, so when I hear somebody screeching, “Heeeeelp! Heeeeelp!” I spring into action. I jolted out of my apartment and checked all the rooms on my floor. Then I sprinted up the stairs to the third floor. The screaming wasn’t coming from there either.

I raced up to the fourth floor, and I heard it loud and clear. “Help! Help me right now!” I crept into apartment 4F and there was Marcy. Laying on the floor. Completely undressed. In a pool of blood. There was blood everywhere.”

I caught up with my friend Lara not too long ago, and she showed up fully exasperated. She arrived at the gym (we were doing a workout together) already sweating, and even before giving me a hug, she held her pointer finger up and then keeled over and placed her hands on her knees. “Jordan, you’ll never believe what just happened to me.” She proceeded to describe the scene above.

Fortunately, this story has a happy ending. Marcy fell off of her bed and cut her knee. Yes, there was a lot of blood, but Lara cleaned her up, got her to the hospital, and the doctors stitched her and had her home within the next 24 hours. But that’s not everything. Lara mentioned how Marcy was so appreciative of her help that she invited her over for wine and pizza later that week.

The lessons shared below are from Lara’s conversation the night her and Marcy had wine and pizza together. A night that began at 7 pm and did not end until 3 in the morning.

After standard pleasantries, deciding which bottle they were going to break out first, and from which pizza place they were going to order, Marcy got straight to the point.

“Lara, I am 99-years old. I have no family, no friends, and I do not love my life.”

“When I saw you come into my apartment the other day and you helped me for no apparent reason, I took that as a sign. You saw me at my worst. Naked. Cold. Alone. Afraid. I think when somebody sees us in our purest, most vulnerable state, there is an instant connection.”

“I am not going to make many more connections during my time left here, but I think I can make at least one. Let’s take this night to connect. Let’s take this time to allow me to share with you my life and all that I have learned. I don’t know you, but I do know me. And I know it’s cliché, but I don’t want you to make the same mistakes I did. I want to share my mistakes, my regrets. So, tonight, we drink, we eat, and we talk about life.”

Lara simply smiled and filled their first glass with a Lambrusco, a sparkling red wine.

1. I Wish I Had Really Learned

“Lara, I was smart. I was really smart. I was top of my class in grade school, college, graduate school. I excelled in the classroom. I got fabulous job offers, especially for a woman in the middle of the twentieth century. I made a lot of money, and I had a lot of power at some big-time companies.

But I never really learned.

I never enjoyed flipping through the pages of a paperback just to learn about the Renaissance through the lens of historical fiction. I never sat in a library understanding the true power of words by perusing through a dictionary or encyclopedia. I never got so immersed in a conversation at a coffee shop in a small town in Italy that I completely missed what was on my schedule for the rest of the day.

Lara, I used learning as an excuse to climb a ladder. I never enjoyed anything I learned, I never found a passion or a true sense of meaning in the work that I did. I knew finance because it would open doors for me. And it did. But it never felt right. I wish I would have done something, learned something that felt right.

You have to constantly learn new things, Lara. That is how you stay current. That is how you can have more conversations. That is how you can differentiate yourself from everybody else. That is how you can adapt. Informal education is our greatest gift, because there is learning everywhere.

Ask questions all day long. Look up the answers on the internet, be informed. Understand what you want to learn about, and then learn about every single thing except that, so you can build upon the excitement when you finally do get the chance to learn about what you desire.

And do me a favour Lara, promise me this. When you learn, you will give your gift to the world and you will teach others. You will not hold onto that information for yourself. You will share it, and spread this beautiful joy to the world, just like I get to do with you.”

Lara simply smiled and filled their second glass with Prosecco, another sparkling wine.

2. I Wish I Was More Willing to Forgive

“Lara, I can tell you countless examples of when this applied to my life. Professional, personal, you name it, I was known for holding an intense grudge. But nothing hurts me more than two scenarios in particular. One in which I was unable to forgive my mother. And one in which I was unable to forgive my closest friend.

My mom and I never had a great relationship. She had a very difficult life. My father left before I was even born, so I’m sure that was devastating. Then she’d go from man to man to man searching for love, support, care. But it seemed she always found the wrong one. She always found the abusive types, the drinkers, the yellers, the criminals, the deadbeats. When I was old enough to understand her pattern, I attempted to put an end to it.

When I was 19, I was already off at college, and I came back to my mother overjoyed about having finally found ‘the one.’ A good egg she told me. And he did seem fine, he really did. Until I saw him one night at a local bar with his hands all over a woman who was certainly not my mother.

I told my mom. I had to, I was honest, direct, no matter the consequence. And she berated me. She called me names I had never been called before. She accused me of ruining her happiness. Ruining her life. She told me she never wanted to see me again. So that’s what happened. I never saw her again. I never forgave her for how she reacted to me that day. I learned she died years later. We hadn’t spoken since that day.

The other person I never forgave was my closest friend. I met him at work. He was strikingly handsome, charming, all that good stuff, you know what I mean Lara. But he was not available. He was married to some trust fund baby, and as flirtatious as he always was, I would not stoop so low as to sleep with a married man. After working together for fifteen years, the day finally came where he told me he and his wife were splitting up. This was my chance. I waited a few months before I finally made my move.

We were walking home after a few work drinks as we often did, and I just threw myself at him. I didn’t have a plan because I just expected everything to fall into place. But he rejected my advance. He told me we were better off as friends, and he didn’t see me that way. I flipped.

I brought up every single moment in which I believed I was the one for him, and he apologized for giving off the wrong signs. He asked if we could remain friends still, but I refused. He moved to a different team within the same firm, but we never spoke.

I never forgave him for not feeling about me the way I felt about him. I lost my best friend.

When it comes to my mom Lara, I want to tell you this. Words are more reflective of the person saying them than they are of the person they are directed toward. My mom said nasty nasty things to me, which she probably would have said she didn’t mean had I given her the chance to apologize. But what I realized was that her words were more reflective of how she felt about herself. They revealed her insecurities, her flaws, her hidden beliefs about the life she was living. When you feel like you cannot forgive somebody because of the words they said, please remember this.

The situation with my best friend is complex. But my main message is this. You want to be surrounded by people who make you a better person. Don’t push people away who make you better. Situations change, feelings change, we must adapt and accept change. I was resistant to change because I was so certain about the future. My interpretation of the future. I wish I could have put my ego, my pride, my feelings aside and just be friends with him, because my life was honestly worse off without him.

Forgive for you, Lara, not for others. Living with the pain of losing somebody because of a grudge or vendetta, or a feeling that I could not control, well it almost killed me on several occasions.”

Lara simply smiled and filled their third glass with a Riesling, a smooth white wine.

3. I Wish I Hadn’t Made So Many Excuses

“Again Lara, there are daily examples I could tell you about. I make excuses about why I was wrong, about why I did something I shouldn’t have, about basically everything that misconstrues me as an imperfect individual. Obviously, I’m kidding, and I know I’m not perfect, but I did think I was for quite some time.

People would ask me, Marcy, why did you never marry? Marcy, why did you never have kids? Marcy, why don’t you make more friends?

I always had an answer. Always. I didn’t marry because I was waiting for my friend to come around. After that, I didn’t think there was anyone else who I could possibly feel the same way about.

I never had kids because I never met the right man. Kids would be a deterrent to my career progression. I’ll have kids when I am finally settled down. When I finally settled down, I didn’t want kids because I didn’t want them to ruin my settling down.

I didn’t make more friends because I didn’t want people to get to know me. I didn’t like other people. I didn’t want to get to know them. I didn’t want to burden them. I didn’t want them to burden me. I had enough emotions to handle, why would I want to worry about someone else’s.

I had an answer for every single thing. And here I am now. Alone. Isolated. Depressed. I am about to turn 100, and I will have nobody to celebrate with except for nurses and hopefully you. I made excuses that all have the same theme. My excuses pushed people away from me, made me even more of a loner. And it’s ok to be a loner sometimes. But it’s not when you don’t even love the person you are spending all that alone time with — you.

Lara, you have to promise me that you will own up to things. You will try new experiences, listen to people when they call you out on flaws you may not see yourself. Be independent, but do not be a loner. Love yourself first, but love others as well. Keep them close, don’t go about this thing all on your own. Admit and be cognizant of what makes you imperfect. Excuses will just continue to pile up until they turn into lies. And you never want to be a liar, Lara. Never. Do me a favour, and get comfortable with saying, I am wrong, you are right.”

Lara simply smiled and filled their fourth glass with a Malbec, a smooth red wine.

4. I Wish I Wasn’t So Closed Off

“This goes hand in hand with my regrets about pushing people away, Lara. I lived such a closed-off life, I have all these stories in my head, all these thoughts, all these secrets. And I have not a soul to share them with. I guess that’s why I’m sharing them with you. I need to let it all out. Everything has been bottled up inside me for so long now.

I remember one time my company made me go to a retreat. A personal development retreat. There was nobody there from my company, nobody there who knew a thing about me. It was my opportunity to share. It was my chance to talk about my life.

But even then, I didn’t. I was so closed off, so afraid of what others would think of me, that I just sat there, and every time they came to me with a question, I’d just say that there was nothing more for me to share. I had no problems, nothing to contribute.

I even went to a therapist one time, and I wouldn’t share with her either. I was too proud. I didn’t want one person to see me differently than I thought I wanted them to see me.

Now look at me. I am going to die with all of these thoughts. All of these secrets. And the anxiety and stress all of this has created for me is immeasurable. Had I shared more about myself earlier on, then maybe I’d have more of a legacy. Maybe I’d have less regret.

Lara, you must live your life with other people all around you. You need to share, you need to contribute, you need to get the thoughts out of your mind and out into the world. When you do this, you will have more peace, you will have less stress, and you will have the ability to live on in the form of stories that others know about you.”

Lara simply smiled and filled their fifth glass with an Aperitif, a nice dessert wine.

5. I Wish I Cared More About Others

Marcy began her final lesson wiping tears away from the corners of her mouth.

“I don’t think I ever truly helped somebody, Lara. I don’t think that in school, in business, or in life, anybody would answer the question, ‘Did Marcy make your life better?’ with a resounding yes. And that is absolutely soul-crushing. I always put myself first. I never volunteered, and I never went out of my way to serve others. Sure, I donated, but that was taking the easy way out.

I never understood the importance of helping those less fortunate. I never experienced the beauty of putting a smile on somebody else’s face. I was so consumed with achieving more, gaining more, accumulating more material wealth and goods, that I forgot about what the most important metric of meaning really is. The quality of relationships you make and the value you give to other people and the world.

Lara, as we sit here and enjoy this final glass of wine, I will keep this short because I know it’s late.

Live selflessly. Not only should you live each day like it is your last, but also you should live each day like it is somebody else’s last. Because you never know what is going to happen to you or to anybody else. Enrich the lives of others to the best of your ability, just like I know you already are. Because you did not have to walk in my door and help me last week. But you did. And here we are.”

Lara simply smiled, and she filled up her sixth glass of wine. As the ladies clinked to an extra glass, Lara finally said:

“Throughout this entire night, I have listened to all that you have learned. I have listened to you forgive. I have listened to you take ownership and not make excuses. I have seen you share and not close yourself off. And I have personally experienced your care for others. Because this conversation has been one of the greatest helps of my entire life.”

As the clock struck 3 am, Lara excused herself and walked out of apartment 4F. “Thank you, Marcy.” She said as she closed the door behind her.

Marcy simply smiled and filled a final glass of wine. The sweetest wine she had ever tasted.

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