‘œThe decision to kiss for the first time is the most crucial in any love story. It changes the relationship of two people much more strongly than even the final surrender; because this kiss already has within it that surrender.’ ‘“ Emil Ludwig

lesbian datingI refer to the Year of Nina as the time period between breaking up with Partner #2 and finally meeting Jeanine. I was in my early thirties, on a dating blitz and determined to find the right girl this time around. I needed to kiss a lot of frogs to find my Princess Charming. And kiss I did! But it never got to that point with Jessica despite ten dates’¦ yes, ten dates. And of course I was keeping track.

Jessica, not her real name, but I’ll call her this because her picture on PlanetOut personals looked like Jessica from Kissing Jessica Stein. However the photo she posted was a profile view not frontal and in person her face was much rounder when looking at her straight on. She didn’t look a thing like Jessica Stein. Disappointment number one.

But I liked her. She was an attorney (I have a thing for ladies of the law!) and by choice worked defending the rights of incarcerated offenders living with HIV. She hardly made any money but owned a home and was building another one on a ranch up by Ojai. She could do this because she received regular ‘œhappy payments’ from her family. Happy payments are the expression I use for trust fund checks and until I ‘œdated’ Jessica, I never knew anyone that got one of these on a monthly basis. She had a privileged upbringing and although she wasn’t quite as rich and obnoxious as Partner #1, she was upfront about her ‘œother means’ as she called it. She was quite thankful it afforded her the opportunity to do meaningful work and yet maintain a nice standard of living. Two homes in Southern California, you get the picture. Nice standard.

So where is this story going? Nowhere titillating. Jessica and I hung out for awhile. Ten times to be precise. I really liked her. She was smart, interesting and a great conversationalist. But I wasn’t getting the romantic vibe from her which was strange since she seemed eager to hang out with me. I figured if she wasn’t interested in being more than friends, then she would just tell me. Why string me along? We met on PlanetOut for God’s sake which means I wasn’t looking for another buddy. I was looking for love or at a minimum, some superficial sex.

Here’s the other thing. I paid for the restaurant dates and hosted her a few times at my place. She never paid for dinner or invited me over to her house. When we did get together for the last time, she picked up the tab. Perhaps out of guilt.

Some asked why I went on ten dates and never made a move’¦ well, it’s not like I’m timid. After all, I’m in sales and certainly know how to close a deal. I also know how to read people and while I thought she liked me, I thought maybe she had intimacy issues. One of those women that needed to take it slow.

So here’s the question with this week’s Sleeping with Money… at what point do you draw the line and essentially say: pay your way if we’re just going to be friends. I felt like she was stringing me along. Not all of us get a happy payment and I had to budget for dates. Let me know what you think or what you’ve done in the past. Comments encouraged below!