My Date with a Billionaire

Peter* is handsome and the founder of a company that takes in over a billion in sales each year. He travels all over the world in luxury, meets with former US Presidents, and is in fantastic shape.

Asked Out by a Billionaire

It’s not everyday that one gets asked out by a billionaire. Perhaps it’s more likely for one to be struck by lightening. 

In the Age of Cyberspace, I was sent a Friend Request by a very handsome man. 

In the Age of Cyberspace, I was able to learn a great deal about this stranger before deciding to accept his request.

The Facebook Down-Low 

Peter loves to travel. He has one sibling and owns multiple properties. Peter has a full head of hair and likes to spend time on the beach. He’s a father. He’s the Founder and owner of a well-known company.

I decided to accept Peter’s request.

Those First Text Messages

Peter was over-the-moon that I had accepted his Friend Request. He wrote eloquently and asked me engaging questions before asking me out to dinner.

“I’m in my ________ home now, but I’ll be flying back to ________ and would love to take you to dinner.”

Peter proceeded to suggest 5 different restaurants, each one ridiculously expensive. He then offered to pick me up or hire a car for me.

“Thank you for the offer. I’ll meet you there.”

My History with Wealthy Men

Years ago, I was with someone wealthy. However, when our relationship didn’t work out, the wealth was used as a weapon:

What Wealth Feels Like

So, it made sense that my spiritual hackles were raised by Peter — an affluent stranger who asked me out on social media.

Still, everyone is different and everyone deserves a chance.

 To discriminate against someone wealthy is no different than discriminating against someone poor.

Our date was set.

The Little Pebble in Your Shoe

You put on your socks, step into your shoes and something doesn’t feel right. You walk around and try to ignore it, but it’s there, you can just feel that something is in the way.

Sometimes it’s the little pebble in the shoe that needs to be addressed.

My little pebble: the age difference.

Upon further internet browsing, I learned that we weren’t ten years apart as originally assumed, nor fifteen years, but 17 years apart.

Does it Make a Difference?

As a social experiment, I’m purposely not sharing which direction this age difference is. For example, is Peter:

  • 17 years younger than me?
  • 17 years older than me?

Why?

 Because it doesn’t make a difference which way the age gap falls, almost 2 decades of “Age Distance” in either direction is significant.

What Does Matter

There’s nothing like preparing for a date with a billionaire to remind someone of what really matters:

Heeding your own inner voice and guidance.

Easier said than done on the cusp of a date with a billionaire. Suddenly, everyone has to give their two cents (seriously, no pun intended;-) As Clint Eastwood says in Dead Pool:

“Opinions are like assholes, everybody’s got one.”

And the unsolicited opinions arrived:

“Seventeen years isn’t so bad.”

“Just go out with him for the experience.”

“You’ll be taken care of.”

“Who cares if you have nothing in common — he’s rich!”

“Let him spoil you. You deserve to be spoiled.”

“When he’s that rich, who the hell cares about age.”

Going Inward

Advice aside, I needed to listen to what thought was important. 

At the end of the day, it’s what YOU think that matters.

When I got quiet, I could hear my voice above the cacophony of others’:

Money comes and goes. It does not make a person. Certainly, money makes life easier. But I do not want or need a man to make my life easier. I want someone in my age range to enjoy and experience this life with on equal footing. The uneasiness in my stomach felt every time I think of this date is my body’s intuition. 

This man seems kind. I do not want to waste his time. He deserves to spend time with someone who will look forward to his company, not one who is looking for the EXIT sign as soon as they meet.

While our financial bank accounts might look a world different, we each carry a mortal bank account and deserve to spend it wisely before our unknown expiration dates.

My Decision

Once I realized that it was better — for me — to cancel our date, I took action.

Peter was a perfect gentleman, writing that he understood and wishing me and my family a Happy Thanksgiving.

My decision to cancel the date wasn’t personal to Peter; it was personal for me.

Peter “got” that. No doubt, he will meet the perfect woman for him.

The Fallout 

As with any decision we make in this world, there are reactions from those well-meaning people in our lives with their buttholes — er, opinions.

When people are disappointed in your decision, remember that it’s about them, not you.

Peter wasn’t offended in the least. He knew my decision was not about him. The age difference was my issue, not his.

My dear family and friends (not all) were overflowing with their opinions regarding my decision. I felt like I was a sport’s team, and they hadn’t liked my last play.

At the end of the day, our life’s choices are ours to live with.

Had I gone on the date or had I maintained my decision to decline doesn’t matter to anyone else — it doesn’t affect anyone else.

People who are close to us often mistake their opinions as ours.

When we are close to someone, we can easily lose ourselves in the story told to us.

But we are not someone else’s story. We can choose, at any time, to get back into the driver’s seat of our life and decide what does and doesn’t work for us.

The Good and Bad of Opinions

Opinions offer opportunities for us to consider other viewpoints and challenge our own. 

The danger of opinions, if we aren’t vigilant, is that they can stealthily morph into our own until we are living the life someone else wanted for us.

Vigilance is key. Paying attention to our body’s reactions to another’s advice. Questioning our reactions yet trusting them to guide us.

There is no wrong decision when it comes from our intuition.

*Name is altered for privacy purposes

The Dating Game

When we alter our perspective, we change our experience.

*Rebecca was a knockout: green eyes, strawberry blond hair and a smile that lit up a room. It’s no wonder *Jon swiped left on her profile. After several texts on the dating app, they made plans to meet for coffee.

A few hours later, the two hugged and Jon said he would be in touch. 

“You better,” she said, her voice a flirtatious wink.

True to his word, Jon reached out after a couple of days, wanting to “play it cool.” However, his mind was already seeing them go on camping trips with his dog and sitting beside her at an Astros game.

                        After what Jon considered enough “polite texting banter,” he asked Rebecca out for dinner that upcoming weekend.

                        With bated breath, he watched the 3 dots surface on his phone…then stop…then start up again. In what felt like an eternity, he received the following text:

                        I can’t this weekend. I’m heading to a family reunion upstate. But let’s definitely get together the following weekend!!!

Crushed, Jon was grateful the text didn’t allow for her to see the disappointment on his face. Instead, he texted back a no-big-deal thumbs up emoji. 

Jon spent the next week researching restaurants and cool things to do in the area. On Wednesday of the following week, Jon texted Rebecca again:

Hey! Hope you had a great reunion with your family. Does this weekend still work for you?

The beautiful strawberry blond texted back within the hour:

I just found out that I need to fly to LA for a work event. I’m sorry for the confusion. But let’s definitely meet up the following weekend.

Jon felt like his heart strings were being pulled against his will. For the past two weeks since meeting Rebecca, Jon had replayed their long coffee date in his mind like a record stuck on the same groove: the angle of her face as she laughed when he told her a joke about getting older, the excitement she expressed when talking about her love of contemporary art. The way it only felt like the two of them at the coffee bar.

The following week, Jon began looking on the dating app again. A few girls “liked” him, and he started to engage in texts with two of them.

The excitement of meeting Rebecca and their potential was fading.

And of course, that’s when Rebecca reached out to him:

Hey! How’s your Thursday going? I’m back in town. Did you have a fun weekend?

Jon’s veins flooded with a dopamine high. 

Good! I’d love to take you for dinner this weekend🙂

Aw. Thank you. I’m just so exhausted. Let’s shoot for next week.

Online dating makes me think of the Hindu parable of the snake and the rope. A man is walking alone in the desert when he sees a rattlesnake. His heart races and his adrenaline is at an all-time high. But before he runs away, he takes one final glance at that snake, only to discover it’s a rope. Suddenly, all the adrenaline and fear left his body.

Our perception creates our reality. When it comes to dating, the myriad of emotions we can experience can feel so personal, so real. But like the weather in the sky, our emotions are temporary. When it’s rainy outside, we don’t take it personally. Likewise, when we experience a negative emotion, we are not the emotion itself. We can observe it and know that like weather, it will change. We have the power to alter our perception, to see the dating world as a rope, not a snake. 

Jon will never know why Rebecca keeps putting off meeting him again. He will never know “the truth” about why she reached out to him if she’s not interested in dating. But he CAN experience a more enjoyable dating life if he’s not weighing everything like that man walking in the desert: fearful, anxious, considering every interaction with a stranger a matter of life and death.

When we consider dating a game, we don’t take the experience as seriously. We can enjoy the moments themselves. We can change our goal from something less lofty (meeting “the” one) to meeting new people (making new potential friends while learning more about what we like and don’t like).  A game is about having fun, not torturing oneself with what ifs and failed attempts at mind reading.

*Names have been altered to protect the individuals.

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Burying Yourself in Dating

Dating while still in the psychological Diet Coke of Denial can be a precarious endeavor, making it that much harder to unearth the truth.

A dear friend of mine recently got divorced. We are talking, recent as in the ink is still drying as I write this. Eighteen years of marriage, two of living together, two kids, two dogs and a house still needing to be sold.

“It wasn’t mutual,” she tells me each time we get together. “I was happy. When he wanted to go for couple’s counseling, I said sure. He kept saying he wasn’t happy.”

Halfway through our lunches, she’ll pull out her phone and ask me what I think of the men she is meeting that afternoon, that night, the next day, and the day after that one.

Before our waiter heads over with the bill, she will repeat those three words from the start of our lunch, “It wasn’t mutual.” No reintroduction to the topic needed; the pain verbally splattered all over her face and hunched shoulders.

“Why do you think he wanted out?” I ask.

“Probably because my ass could double as a pincushion now,” she laughs.

Her laughter is a forced sound that renders both of us uncomfortable. I let the sound fall between us and land with a thud. We both know her ex found her physically desirable and couldn’t have cared less about her weight.

“You know I made that big financial mistake, but I apologized. Geesh, move on,” she said, flipping through the latest Hinge profiles on her phone.

My friend has alluded to the “big financial mistake” for years now, but I still don’t know what exactly she did wrong that her ex can’t move past. We are close and yet this financial “mistake” remains a mystery only clear to her ex.

Ironically, my friend is a private investment banker. Her career is literally about helping affluent customers make sound fiscal decisions. 

My friend is in the Diet Coke Denial of the most sacred relationship: the one with herself. Deep down, she knows exactly why her ex can’t move past whatever she did or didn’t do fiscally. Deep down, she knows it was wrong to cover up whatever it is that she did. Deep down, she knows her self-degrading humor regarding her derriere reflects her self-esteem and sense of self-worth.

Unfortunately, instead of getting real with herself, she buries the truth and the unspoken shame she feels. Instead of facing fears, she fabricates online filtered profiles of herself from 10 years ago, before her weight gain and financial deceit. She writes about the importance of honesty in a relationship and notes she is “looking for something casual.”

“I just want to have fun,” she tells me.

And then:

“It wasn’t mutual. I was happy.”

Until we get real with ourselves, how can we be ready to date? 

I think of the famous Sir Walter Scott quote:

“Oh, what a tangled web we weave, when first we practice to deceive!”

My friend, in an effort to protect her already broken heart, is deceiving herself and, by extension, the men she is meeting. It’s a tangled mess only to be cleared up through the inner work she needs to do. Denial is the Chinese finger trap of healing: the more we fight to deny the truth, the harder it is to break free and live the life we are meant to live.

Dating Red Flag: The Smooth Operator

The old adage: If it seems too good to be true, it probably is exists for a reason.

FaceTime first dates are a popular experience in the world of online dating—particularly for those finding potential in someone who is geographically less desirable. A few short months ago, when there was still a wait list to get a vaccine, my cousin *Jeani called to share the exciting news: “I have a date!”

The “date” was suggested by a fellow (albeit former) Bostonian who, like Jeani, now lived in California. The divorce father of three girls lived in Silicon Valley—a good five hours drive from my cousin (Los Angeles).

Jeani is a single mom of four in her late forties. She is a full-time veterinarian and works long hours. When most men find out that she A) has more than 2 kids and/or B) is committed to her job they C) run away.

“But this one is different. He thinks it’s cool that I’m a vet and didn’t think twice about me having 4 kiddos. He asked if I wanted to Facetime tonight! And he’s CUTE!”

The next morning, Jeani filled me in on the juicy details: Eric found Jeani gorgeous (He even used the word “mesmerizing” to describe her eyes) and told her he was already “falling in like” with her. He said he’d drive down the coast to spend the coming weekend with her.They talked for almost 3 hours. He went so far as to suggest that their next trip home to Boston be together “to meet each other’s parents.”) 

“He said he’d call me this morning.” Her voice was dancing.

Unfortunately, the morning came and went without a word from Eric. Then the afternoon arrived along with the evening without so much as a text from the flattering Bostonian.

Jeani called me that night, the pain in her voice palpable: “He said he’d call. Why hasn’t he called?”

The next morning, still no word from the man who was “mesmerized” by my cousin’s eyes. By evening, Jeani decided to text him.

“How’s the Smooth Operator doing? Still planning to spend the weekend in LA?”

Within minutes, Jeani’s iPhone starting ringing for Facetime. It was Eric.

Only Jeani was about to see her next patient, so she couldn’t take the call. She Facetimed him about an hour later. Eric didn’t pick up. 

“Try me again.” Jeani texted Eric.

Silence. 

Since then, Jeani can see Eric on the dating site they first met on.

“It hurts. I don’t know why it hurts, but it does. I didn’t even know the guy. So why does it hurt?”

“It hurts because someone played with your heart. It hurts because it’s painful to know that there are people out there who treat dating like a game, who prefer to find pleasure in cruelly leading someone on instead of engaging in an authentic conversation. It hurts because we don’t want to think that he is a part of what makes up our world, our human race.”

I get Jeani’s pain because I’ve been there. If you’ve lived long enough, you’ve experienced the disappointment of someone not being who they represented themselves to be. The high of expectation and the low of reality creates a semi-crash that wounds (temporarily).

It’s always a red flag when someone comes on too strong or says all the “right” things—an auditory confection a vulnerable heart yearns to hear. Be wary of the “Smooth Operator.”  They got that way after lots of practice.

*Name has been altered for privacy purposes.