I’ve had the luxury of having dinner with Jack before. To recap, Jack is a once-a-week regular who has been coming to see me for the past year. That’s a lot of sessions. And Jack respects my boundaries. He happens to be in his mid-fifties or so and married to a woman who has no interest in sex.
Jack has wonderful taste in food and let’s me pick wherever I what, “Get whatever you want,” he always says and once I made a selection, he always chides me to get the biggest size or an appetizer. These extras are the type of thing I’d never allow myself to consider, particularly growing up. An appetizer to me has always been the small snack you eat before a fancy meal so you can order something cheaper, but with Jack he acts so carefree like it’s not going to matter one iota to him; it won’t cut into his spending money or be a sad, sorry surprise when he gets his credit card bill. It took me a few times to eventually indulge Jack in picking something of what I actually wanted, not what I thought he’d want me to pick, because he was paying.
The only bad thing about meeting up with Jack for dinner is that he tends to get there early. I try not to be late when meeting anyone, particularly clients, but I’ve noticed with Jack that even when I show up five minutes early, he’s always there, looking up at me and smiling, relaxed as if he owns the place.
Jack is all grace, which might seem like a strange thing to say about a guy, but trust me, if you saw him in action, you’d know what I’m talking about. He’s the kinds of guy that could get a flat on his Lexus, change the tire swiftly, coolly and competently and manage nary a drop of dirt on his freshly-laundered, crisp dress shirt. I’m fairly certain that he’s never left his zipper undone (and trust me, I’ve seen plenty of my clients leave in a daze and neglect that area) or trip on a slightly upturned sidewalk edge. And then there is me. Which is why I hate crossing a room with Jack looking at me. It’s feels like moving through water. I’ll tell the hostess that I’m meeting someone and she’ll smile as if Jack has told her lovely things about me and then point in his direction. At which point his Alexa-radar triggers and he looks up, smiles, and I immediately feel as if the entire restaurant is looking at me. I’ve been told I’m paranoid, btw. I smile back and move through the room, skirting around tables and people in a haphazard, twister sort-of-way.
“Hey Beautiful,” he says as he pulls the table out with one smooth gesture, allowing more room for me to squeeze behind and sit down. He puts down his phone and gives me his full attention.
“It’s been a long time,” he says.
It’s been two weeks.
“I figured you were away when I didn’t hear from you last week.”
“Oil convention,” he says.
Jack sells some sort of equipment to oil companies, a process called fracking, and it has worked out well for him. He's self-employed (like me) and the thing I love about him is that he is entirely self-made. He never went to college and yet he's making a very good living (what I am striving for), despite the fact that he never went to college.
I won't bore you with our whole entire dinner talk, but I told him I was interested in his Sugar Daddy proposal and he was excited that I was interested. And surprised. He suggested that I think about exactly what I had in mine and he'd think about what he wanted. And then meet again to iron out the details.