Breaking the Rules

Lavender shirt, black pants, black shoes. Tall. Late 40’s, early 50’s maybe. Very good looking. Slightly weathered skin but nice blue/grey eyes, and a devilish smile. We met for lunch in the restaurant of a 4 star hotel close to downtown. He greeted me with a big, excited smile and offered me his hand to shake, but I went in for a small one armed hug and kiss on the cheek. For some reason it felt more natural, and I didn’t hesitate. I don’t think he minded.

A few moments after sitting down at the table across from one another, he handed me a small blank white envelope. I said thank you and slipped it into my purse beside me.

He was so nice, so easy to talk to, so solid and confident, and I couldn’t help being attracted to him. He was quite older than me of course, but it didn’t matter. Could I actually see myself dating this one…?

If only it were that simple. He spoke about his wife, I guess I shouldn’t be surprised – though the last two men I went out with were indeed single, to the best of my knowledge, at least. He went on to tell me how she became very depressed after the birth of their second son. She was raised Mormon with the belief  that having children would bring all of the joy and happiness to the world, and to her life. After son number two, she did not feel the joy, or the happiness, and she checked out. She now has a pill for every mood, every section of the day, and her emotions are no longer governed by the events and people in her life- but from the effect of whichever pill she popped last. He is lonely, he has lost the excitement, but he will not leave the marriage, and neither will she. So he does what he has to do to survive each day, living in a loveless marriage void of intimacy and affection.

It’s a sadly romantic story that begs just the slightest amount of pity, while almost absolving you of any guilt you might feel in regards to becoming involved with such man. I wondered how his wife would tell it.

Our lunch lasted an hour exactly. We walked outside, hugged, and as I began walking off, he asked me how he could get ahold of me.

Oh right – and so I gave him my number.


What did I just do?? Only 3 dates in and I am breaking my own rules! This wasn’t fair. If that was all it took, I don’t stand a chance. He caught me off guard, he was so smooth and so normal and so… handsome.


Back in my car I opened the small white envelope. Inside was a hallmark card that simply said “Thank You” in swirly gold letters. Inside the card was 4 $50 dollar bills. I put the bills back inside the card, and the card back inside the envelope, and smiled as I drove off.

He texted me a few days later, I had almost forgotten about him by then.

“Hello JAG, I’d love to take you to lunch again next week. Let me know if Tuesday will work.”

Oh no. A second date? Will I be breaking two of my rules with this one? He seemed harmless enough. But I needed to make sure.

“Just lunch?” I replied.

“I’m up for whatever else you’d like to do. Shopping? Spa? Hot Tub? Just lunch is fine too, if thats all you’re up for. I just want to see those lovely blue eyes of yours again.”

Well that was not the response I was expecting. My mind took me over to our towns high end shopping center, where I imagined us going in and out of each store, a trail of receipts and shopping bags in our wake. Well, that would be fun. But at what price? What do I have to do…? I imagined what “Spa” and “Hot Tub” really meant, and decided not to fantasize about those options for now.

My third rule – no intimate affairs with married men. I have already broken two – I gave him my number, and I was about to give him a second date. I needed to draw the line somewhere, and this seemed like a fine place to start.

“Just lunch sounds fine.”

We agreed to meet again the following week, on Wednesday this time. We had a very pleasant lunch sitting across from each other at the outdoor courtyard of another very high end restaurant downtown. I got the salmon, he got the sea bass – after making sure it was not “chilean sea bass” which is apparently a knock off – a fish that was originally named the “chilean tooth fish” which as you can imagine did not sound nearly as appetizing. Only wild caught, European Sea Bass for our man.

Just as he was asking for the check, a peculiar insect landed on his lip and he immediately brushed it off. It fell onto his napkin which was resting in a heap on the table, and we watched it walked back and forth across the fabric, poking and prodding and inspecting the material with it’s many legs and antennas. Neither of us recognized or could name the creature. It looked sort of like a beetle, with a flat almost round back, and long skinny legs. It didn’t seem to be able to fly, it didn’t have wings, but rather hopped around. When we asked the waiter if he could identify the insect, he leaned over our table to take a closer look and said “Oh yes. Why, this is a native bug, it is harmless, it does not bite.”

A native bug. Harmless. Doesn’t bite.

After lunch, he asked if I’d like to go on a walk with him so we could talk more about what we are both looking for. Gulp.

As soon as we stepped outside, He handed me a small tan envelope which felt like it contained another card. I said thank you and put it right into my purse, and we made our way down the street into the upscale neighborhood that surrounded our downtown.

“So, what were you looking for when joining this site?” Crap. I hate this question. Can’t we just carry on in this vague and obscure world where I continue to meet you for lunch, you keep slipping me $200, and we never need to discuss or address what you or I are really doing here?

“Well,” I begin cautiously. “Clearly there is the financial draw. I am a student, not making much money right now, trying to focus on my studies and my art. And then there is the draw of meeting interesting men – older and hopefully wiser, who I could maybe learn from. I enjoy meeting people and hearing their stories too, which is inspirational. So while the financial aspect is what initially drew me in, I have been enjoying my dates so far.”

Perfect. Just vague enough to dodge the naked elephant in the room, while still answering the question in its entirety. I think I did well! Right?? But he wasn’t going to let me off the hook that easy.

“It’s worked for me in the past like this. I have a mistress, I help out financially, I have secured apartments and cars for the women I have seen, and paid for whatever they needed. Always just one woman at a time, I will add. The last women I saw met with me two or three times a week. I would go over to the apartment I rented for her and we would mostly cook food together and fool around.”

Gulp again.

“Didn’t your wife wonder why you were paying for a random apartment?” I couldn’t help myself, it just came out. He laughed, as if that notion was as absurd as the beach being upset that a few grains of sand stuck to the bottom of your sandal as you walked off it’s shore.

“There is so much money floating around, going here and there. I write so many checks throughout the week between the gardner, house care, kids, care givers, lessons, gym, trainers etc. On top of that, I handle the finances.” Basically, the money isn’t missed, and a few thousand dollars each month slips away easel unnoticed. Interesting. Thank god I love my apartment and wouldn’t dream of moving into a newer, nicer one to be this mans personal Rapunzel. Although he was still charming, tall, and handsome as ever…

“To be perfectly honest,” I continued, “I don’t see myself in that position. I am not necessarily interested in that sort of arrangement of intimacy, but I do enjoy your company. I understand if you would like to move on and find a woman more suited to your needs and wants at this time.”

He wasn’t going to give me up that easy, either.

“We can go slow. Continue to get lunch together on Wednesdays, and continue to get to know one another. I am fine with that. But just know… the more money I give you, the more I will try to kiss you, if that is ok, of course. So you set the rules and you set the boundaries and just let me know what is ok.”

Well then. I did my part, I was open and honest, and he did his. Right? If he wants to continue to see me, I wouldn’t mind. I know it’s entering a danger zone. I know I have stepped foot onto the slippery slope, wearing heels to boot. I know I must watch my step with this one.

He walked me back to my car, I gave him a hug and we said our goodbyes. No kisses.

Until next time… if there is a next time. Now that he knows where I stand, I’ll leave it to him to decide. But men always want one thing at the end of the day (or in the middle of the day, in this case) and that is of course, Sex.

But can you blame him? After all, he is just a man.


Military Man

He is in the military, much younger than the last. 36 years old. He lives in Monterey, and I am still not sure of his name – Tom maybe? Yes, let’s just call him Tom. He used a fake name on his profile, this I remember. But don’t we all?

He was quite cute, though also a bit shorter than me. Fit. I could tell he works out. Nice eyes and smooth clear skin. He was very easy to talk to, and seemed very pleased to be there with me. Being with him felt much like a regular date, we didn’t look too unusual together, sitting across from each other in the ocean front eatery in the cozy village of Capitola. Two minutes into taking his seat across from me he opened up his wallet and handed me two crisp $50 dollar bills. Well, That’s out of the way.

He has been oversees in Afghanistan, and many other places, for a very long time. No women, apparently. He explained that he was so lonely over there he needed to find a girl for when he got back. After browsing the web he stumbled upon a popular sugar daddy type website and began lining em up. Upon his return to the States he had his pick, and decided to fly a lovely young lady up from LA to live with him in his Monterey home. She wouldn’t work, she made a mess, she drained him, she wouldn’t do anything. Most importantly, he said, she wouldn’t leave.

One bad experience after the next led him to sign off, and switch to the less aggressive and more illusive website where he met me.

“But why join this type of website at all?” I was curious. He didn’t seem like he really needed to be on any such website, at least not at first glance.

“I don’t like the games,” he said. “I like everything to be straight forward. I am a giver, and enjoy the finer things in life. I enjoy beautiful women. And I have an easier time finding them this way. After all, look who I am sitting across from. Can you blame me?”

Tom mostly talked, and I mostly listened, though he was polite and did ask me a few questions about myself. I don’t like it when my dates ask me questions about myself… that’s not the point. Not only do I want them to know as little about me as possible, I want to know them. I want to hear them.

He was very taken with me, and very eager and excited to keep me in his life. He talked of road trips to Oregon, Big Sur, flights to Hawaii, and even asked me if I would go to the military ball with him in December.  He will buy me a dress for the occasion, he said.

“It should be long, black, high slit on the side, not too low cut, but definitely sleeveless…” He smiled at me. “Other than that, you can pick out whichever one you want.”

Well, December is in quite a long time, thankfully. Tom and I will be a thing of the past by then, and I will have many more stories to share – none of which will include me attending a military ball in a long black dress with a thigh high slit, sleeveless, but not too low cut…

It’s been a pleasure, Tom. Thank you for meeting me and for an enjoyable dinner, and of course, thank you for the cash. I am certain you will have no trouble at all finding a fitting date for the Ball, but I am not your girl.

I am no one’s girl.

My First Rodeo

I arrived 20 minutes early. I sat in my car for the first 10, and then slowly made my way towards the front door of the restaurant located in the corner of small shopping strip off the main street.  I wore my off white sleeveless silk blouse, tucked into navy blue fabric pants that cut off at the ankle, with shiny black pumps. I wanted to dress as though I was going to a job interview at a law firm – not like I was getting paid to go to dinner with a man who could almost pass as my grandfather. I was the only person around, he surely had the advantage – he could drive past, see me, change his mind and gun it in the opposite direction…

He did not, however. Only a few short moments went by before I saw a man pull up in a shiny new BMW. He stepped out, and I knew right away it was him.

He was short. Very short – much shorter than me, with round thick rimmed glasses, black beard, and smiling, boyish eyes. He wore khaki slacks and a dark button down beneath a warm brown vest. He approached me with a wide smile and took my hand in his. I felt relieved. I liked him right away.

“Excuse me,” he said, “but I was not expecting you to be early as well – I need to make a quick stop at the store next door. It’s right here.”

I was friendly and easy going. “Of course! Would you like me to come with you?” He shrugged with those same smiling eyes of his and gestured towards the store, offering for me to accompany him. We stepped inside and he walked straight for the ATM. Oh right, I thought. No shame here. Is he going to just hand it to me? Nope. He took out his wallet and put the bills inside, and we walked back out towards the restaurant.

We were the only english speakers in the small and homey yet upscale Japanese eatery where all of the servers and wait staff knew him by name. The very same exact name (first and last) as my great uncle who I adore, ironically. I will call him Mr. Fox.

“Shall we bring you your bottle Mr. Fox?”

The waitress brought out a tall half-full bottle of sake with a tag around the neck that read “Fox.” I wondered briefly about the young lady whom he had surely started this particular bottle with that we would now be finishing together. The waitress poured us each a glass, and when she was finished he asked for two more glasses. When they were brought to our table, he filled them with sake, walked over to the bar and set them on the ledge for the chef and server. When the server noticed, he brought his glass of sake over to our table, bowed and took a drink with Mr. Fox, then exited. Well that was different. How thoughtful…

There we were, sitting, facing each other across a very small candle lit table. I felt very natural and very calm. Just your run-of-the-mill dinner date… but I am 26, and he is 62, and he handed me a blank white envelope with $160 dollars inside. For what? Meeting him for dinner, no strings attached.

He was married once, then divorced many years ago. No children. Another lifetime, he said. These days he is single and alone, or more accurately, lonely. We sat there eating various forms of raw fish and rice and drinking sake and talked for 2 and a half hours. We talked about film, art, music, shared stories.

“I’ll give you $300 if you can guess what I majored in!” He challenged with that mischievous look. Well, I thought, It can’t be anything obvious… surely not computer science, or mathematics. He gave me 3 tries – but I struck out each time. “Early childhood development!” He said triumphantly. I must admit that I was amused and surprised that this successful tech executive from the Midwest who had landed himself out on the West Coast kicked off his career as a Kindergarden teacher.

He continued. “Now, for $1000, guess what my next job was.” Shoot, I thought. I’m not going to get this right – but how nice would that be! I gave it a shot but low and behold I had no idea. Ready?


Who knew. He liked this guessing game, and he liked to amuse. Mostly, he liked to talk, and to share his life, which worked out just fine for me. I loved to listen.

He was kind, nice, smart, funny, and easy to talk to and I did not even notice the time fly by. After I left, he messaged me with a few film titles that he recommended I watch, and told me that he had had a wonderful time and would love to see me again.

I had a nice time too, Mr. Fox. But I do not see us progressing romantically. It was lovely to meet you. I’m sorry we will not work out, but I am thankful for dinner, great conversation, stories… and for the cash of course. While this may have been my first rodeo, I am no stranger to letting a man down easy.

Would I do this a hundred times over? Yes, I am afraid so.

What can I say. I am just a girl.

Slippery Slope

Watch your step…

Have you ever done something you never thought in a million years you would ever do? Something that questions your morals, your upbringing, your religion, your mother, your father, your community, something that forces you to re-configure your entire perspective on good vs. evil, right vs. wrong…

Something that if you did it, it would mean you aren’t quite “you” anymore. After doing it, you simply cannot be! How could you? Because everything up until that point, every word you spoke, every thought you thunk, every friend you made, everything that defined you was rooted in all of the above.

So what now? What happens after you dip your pinky toe into the pond, and before you know it – there you are standing in the middle, tilting your head side to side trying to get the water out of your ears.

It starts with dinner. Or lunch even. Get paid $200 to wine and dine at your town’s finest eatery, no strings attached? Yes please – whats that? Oh, yes I would like a box, thank you. And how about getting $2,000 for lunch in a private hotel room – minus the wine and dine (let’s not kid ourselves). And have you considered pocketing $10,000 for a weekend getaway? Maybe a private island off the coast of Maui… No? Perhaps $50,000. Shopping, spa, hot tub… Oh but don’t worry, we can just do lunch, if that’s all you’re up for.

I just want to see those lovely blue eyes of yours again.

Everyone has a price.

What’s yours?