I was at home looking through my credit cards statements to see if I had enough credit to organise a Tinder date. While I had been on 100 straight Tinder dates without having sex, I was a sucker for punishment, and perhaps date 101 would bring me the woman of my dreams, IE a woman I could have sex with.

As it turned out, I had maxed out all my credit cards and it would take me six months to get back in the black. Sexless dating wasn’t cheap, and my dodgy investments were enough to negatively offset my hefty lawyer income. While my investments made me a tax-exempt citizen, I wondered whether it wasn’t preferable to pay tax and have money.

Unable to afford another Tinder date, I contacted my ex-girlfriend, Rebecca. We had broken up after my many failed attempts at cheating on her. However, as I had never sealed the deal with another woman during our relationship, I hoped that time had healed all wounds.

“Hi, Geoffrey. It has been a while. What’s up?” Rebecca said.
“I have been missing you. How about meeting up for lunch?” I replied.
“Have you missed me, or have you missed having sex?” Rebecca asked.
“Are those options not the same?” I asked.
“Okay, I guess. Can you meet me at Cargo Bar at 1 o’clock today?” Rebecca suggested.

‘Wow, she is keen. Why have I waited so long to contact her?’ I thought and remembered my predicament. I was too broke to pay for lunch.

I didn’t want a repetition of my library date with Emma, so I decided to be forthcoming about my situation.

“Umm Becky, there is one thing you need to know…” I said.
“Don’t say you infected me with any STD’s?” Rebecca exclaimed.
“Umm no. However, I am too broke to pay for lunch.” I admitted.
“Wait, aren’t you a successful lawyer?” Rebecca asked.
“Yes, but an even worse investor,” I admitted.
“Okay, I’ll shout you lunch. See you at 1,” Rebecca replied.
“See you at 1,” I replied and hung up.

I smiled as I put down the phone. I had secured a free lunch, and with a bit of luck, I would also secure a session of naked yoga. The Duracell Bunny was ready for action.

***

As I met Rebecca at Cargo Bar, she was as okay-looking as ever, and I wondered why I had put so much time and effort into unsuccessfully cheating on her. We had gotten along well, and if I had behaved, we would still be together. I reminded myself that it hadn’t made sense to settle for the okay option when I was young and still had dreams. However, now that I was older and indebted, an okay relationship was better than a frustrating trek in the dating wilderness.

Rebecca approached me and spoke. “Hi, Geoffrey. It’s nice to see you again. Alas to be honest I accepted in the hopes of getting a free lunch. Then again, I assumed you called me hoping to hook up, so as it would seem, neither of us get what we want.”

Ouch, this was not the rekindling of the flame I had hoped for. I cleared my throat and spoke, “Look, I am sorry about asking you to pay. I’ll make it up to you.”

Rebecca shook her head and replied. “It’s not about the money. We live in the year 2019 and I believe in gender equality. I am happy to pay for lunch.”
“So, what is the problem then?” I asked.
“The problem is the multiple times you tried and failed to cheat on me,” Rebecca replied.
“Woah, I never cheated on you.” I objected.
“That’s because you always failed. Imagine how demoralising it is to be with a guy who always tries to cheat on you, but never succeeds. If you succeeded, I would at least know you were an alpha male that others yearned for. Yet that wasn’t the case for us, was it?” Rebecca ranted.

I didn’t know how to respond to Rebecca statement, so I sat quietly for a bit. A minute later a waitress delivered two medium-cooked steaks to our table. While this was what I would have ordered, I was surprised because I hadn’t ordered anything.

I looked at Rebecca and spoke. “Hey, did you order the steaks before I arrived?”
“Yes, I promised you lunch and I knew what you wanted. Let’s eat. I need to go back to work soon.” Rebecca sniped.

We ate our steaks in silence. I was about to leave when Rebecca smiled and spoke. “Hey, Geoffrey, one of my college professors, Kanika, would love to have dinner with you tonight. Are you available? It’s her shout.”
“What’s the catch?” I asked.
“Nothing,” Rebecca said and smirked, “I am just helping a friend of mine meet the man of her dreams.”

I hesitated for a bit. I sensed that my ex was pranking me, but I could not be sure. “Okay, I’ll go. What does she look like and where do I meet her?” I asked.
“Meet her at Le Petit Frog Restaurant at 7 PM. This is her photo.” Rebecca said and showed me a photo of a Thai woman in her late thirties.

I looked at the photo, and while Tanika was by no means a stunner, her features were acceptable and better yet, she was paying for the date. It was time to break my dry spell by having sex on my 101^st date.

“Great. Tell her I am happy to meet her.” I replied.
“Good luck,” Rebecca smirked and left the restaurant.

As I returned to my lawyering office, I felt a mixture of anxiousness and anticipation. I was anxious because I was unsure of my ex-girlfriend’s intentions. Yet I also felt anticipation because Kanika seemed like a safe bet, and it was time to break my long dry spell!

***

“Hi, Geoffrey. Before we begin, I would like you to answer two questions to ascertain our compatibility.”

I looked in bemusement at my date at the restaurant. Was this a date or a session of paid market research? In any case, I saw no problem in answering any pre-qualifying questions now, as this would save me a couple of hours if my answers were incorrect.

“Ask away,” I said and smiled.
“How high are your IQ and how many have you slept with?” Kanika asked.

‘Wow, this was direct and unexpected.’ I thought and wondered whether Rebecca had hidden a camera somewhere. It might surprise the reader that I am highly intelligent, and I was the top student in my high school class. Unfortunately, high school never taught me common sense.

“My IQ is 135 and I have slept with a dozen or so women,” I replied.
“Excellent answers. And how many men have you slept with?” Tanika asked.
“I haven’t slept with any men,” I replied.
“But would you consider it if the opportunity arose?” Tanika asked.

Ouch, this was a tricky one. My honest answer would be. ‘Fuck that, I am not a bloody pooftah.’, however, that answer would reduce my chances of having sex tonight, so I replied. “As humans, we should always keep an open mind to find novel ways of expressing our sexuality.”

“Excellent. You passed the test. Let me shout you a $199 French degustation dinner.” Tanika said and smiled.
I smiled back. While I would have preferred $199 spent on drinks and marching powder, it was still flattering to be on the receiving end of an expensive dating experience for once.

As we ate our fancy French meal, Tanika spoke about her gender studies research. It was an okay experience and Tanika’s vocabulary revealed that she was also intelligent. Meanwhile, her far-fetched left-wing conspiracy theories proved that she lacked common sense. So, I guess that we were compatible.

At the end of the date, Tanika looked at me and spoke. “I had a great time with you, Geoffrey. Would you mind coming to my place so we can have sex?”
“Sure, why not,” I replied.

While Tanika was far from the prettiest woman I had been on a date with, she was the first one to spend $200 on me. It was payback time, and the Duracell Bunny was ready for a night of passion.

***

“Is this your real penis?”

Tanika’s comment confused me, as we were about to set up a session of naked yoga.

“Of course, it is. What are you talking about?” I replied
“I cannot have sex with you, Geoffrey,” Tanika said and rolled away from me.
“What is going on?” I asked.
“I am a ladyboy, and I am only attracted to mengirls, IE. men that used to be women.” Tanika revealed.
“I don’t understand anything at all,” I said, still confused by the surrealism of the encounter. “Rebecca told me that you were my perfect match, an intelligent woman who had converted into a man. I am a man, Geoffrey. I am not attracted by other men. Please leave my apartment.” Tanika said.

I pulled up my pants and I hurried to leave Tanika’s apartment. I guess Rebecca got the last laugh for the many times I failed to cheat on her. Fucking hell, I almost had sex with a transvestite. Yuck!