The Stumped Attorney

William. Although something tells me that is not his real name.

“How would you feel about your daughter being on here, William?” I asked him, referring to the website that brought us together.

He was a tough one, this seasoned patent attorney who sat across from me in a cute Italian restaurant in the La Jolla area of San Diego, but he couldn’t get anything past me. That question seemed to have the same effect as me pulling a gun out of my bra and aiming it at his temple. But you wouldn’t have noticed, not unless you were really watching, really paying attention. There it was, the quick quiver of his lip, the color in his face, the ever so slight change in expression, all there and then gone in a flash. He was not expecting a question like that, although it was on topic. I could tell he was just slightly perturbed – even after regaining control over his facial expressions.

“Oh well that would be none of my business. Just none of my business.”

He tried to play it cool. Tried to play it off and approach the question from a nonemotional, totally logical standpoint. After all we were in the middle of quite a long conversation of morals ethics judgments and social norms. It was not meant to put him on the spot, or make him feel uneasy. It was a relevant question, and a genuine question. And what can I say, I was curious. But all he kept on repeating was the same line he outputted the first time I asked.

“What else can I say. That would just be none of my business.”

“Well then, that is very progressive of you, William. Not bad for a 45 year old man like yourself.”

“45? is that what I put on there?” He said with a smirk.

“Yes.”

“Oh, well I lied.”

“Oh, Well… I lied too,” I offered. “And I won’t say about what.”

He looked at me for a few moments, smiled and took another bite of his pasta something or other.

After dinner he walked me to my car and as he handed me my to go box of leftover bucatini alla Sorrentina, he took my hand in his and with a smile said, “Goodnight Tiffany. It was truly a pleasure.”

 

Friends with (My Kind of) Benefits

SO. I haven’t written in a while, and I apologize (to myself) but I will try and double back to share some “unconventional” dating stories in the next few posts.

I’m pretty sure I’ve managed to successfully hack sugar-daddy-dating system. Some how Lunch is totally fine with us being friends, platonic relationship all the way – no hand holding, no kisses on the cheek, no nothing. I clearly stated that was all I was capable of being with him, as he is married… and well, twice my age, but for the purpose of this argument we will stick with the former excuse. And guess what? He still wants to take me out for lunch, take me shopping, and has offered to continue to help me out financially when I need. I’m honestly confused and amazed and I’m not sure what’s in it for him. When I asked, his reply was equal parts sadness and sweetness:

“I’m lonely, and I enjoy seeing you.”

We met at the mall yesterday and he took me around to all of the different high end stores, bought me two new dresses, pair of shoes, purse, and a gorgeous raincoat that I would never in a million years be able to afford on my own (well on second thought, maybe at this rate…).

No price tag phased him which is still hard for me to wrap my head around. $1000 for a dress?

“Go ahead, try it on! If it fits, its yours.”

He paid cash for everything (he must carry around with him close to $5k in hundred dollar bills) and made it a point to give me all of the receipts. It didn’t occur to me why until my girlfriend pointed out that I can go back and return everything for cash. DUH.

I don’t think he cares if I keep the items or return them. He enjoys spending time with me, and it’s more fun to go around shopping than just eat together or take a walk. He wants to help me out financially but maybe it just feels nicer for him to buy me things instead of flat out handing me $500 or $1000 every time we meet. I get it. I like it. No complaints here!

Anyways, I’m still not totally sure how I feel about this whole thing. But it is feeling less and less weird, and I attribute that to my being completely forth coming regarding my intentions and limitations on our relationship. One thing I’ve learned – it is best, especially when navigating such a slippery slope, to be as straight forward as possible. I find the men appreciate it, it’s a breathe of fresh air for them, as they are used to women trying their best to manipulate and persuade them this way and that, telling them everything they think they want to hear. Not my style. And hey – It doesn’t always work out, but the ones who say sayanara after I drop my short and to the point “friend zone” speech, well, one less fella to worry about.

The best part about Lunch is how easy it is for us to just, hang out. Wether we are just getting lunch, or walking around a mall or anywhere else, he has never made me feel weird or uncomfortable, never walked too close or tried to put his hands on me, and our conversations flow. Obviously he is smart and successful and something of a socialite and it’s fun and entertaining (and dare I say educational??) to simply be around him.

And again, who knows how long this thing will last. I’m still waiting for the day he gets bored of me and starts looking for an actual “sugar baby.” But until then, I’m young, free, beautiful, and looking for some good stories to tell when it’s all said and done. And who am I kidding –  a Herve Leger bondage dress or two along the way wouldn’t hurt. 😉

-JAG

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.

Wait.

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.

Whoops.

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.