Authors: Jackie Pilossoph
The bar at the W is famous for two things; its Cosmopolitans and its reputation for being the easiest pick-up joint in Chicago. So, here I sat, dressed in my Lucky Brand jeans and a navy Polo shirt, ready to find myself a woman. Not just for sex, though. Well, yes, for sex, but specifically for sex to lead to a pregnancy.
Already on my third martini, I decided the bar wasn’t living up to its expectations, and I’m not referring to the drinks. Girls weren’t so easy to seduce under these times of extreme pressure. I’d already talked to three women and had been unsuccessful in wooing any of them into bed for the night.
The first girl turned out to be meeting her boyfriend there. After buying the second girl two Grey Gooses (or is it Geese?) on the rocks, I found out this hopeful mother of my child was a lesbian. And ironically, the third girl was pregnant! I found this out when I went to buy her a drink.
“What can I get you?” I asked.
“Just a Coke please,” she said with a smile.
“Aww, come on, let me buy you something that costs more,” I flirted, “How about one of these?” I asked, motioning to my Cosmo. And that’s when she broke the news to me.
So here I sat, still alone and still desperate and determined to find someone. I told myself I wouldn’t leave this place alone tonight, no matter what. Suddenly, to my unexpected surprise, my luck changed. A very attractive woman sat down next to me.
“Hi,” I said to this beauty with the prettiest pink frosted lips I’d seen all night.
The girl gave me a courtesy smile that was a bit standoffish. Then she waved the bartender over.
“What can I get you?” the bartender asked her.
“Whatever she’s having, I’m buying,” I said.
“You don’t have to do that,” she replied. Then she looked at the bartender and said, “I’ll have a vodka and cranberry please.”
The bartender went off to make the drink.
“Thanks,” she said, shyly.
“No problem. I’m Danny,” I said, holding out my hand.
She shook my hand and said, “Look, I don’t mean to be rude, but I’m not looking to meet anyone.”
“Neither am I,” I charmed, “Tell you what. Let me buy you the drink and we’ll just sit here and not talk.”
“Why would we do that?”
At this moment, I noticed her pretty cheekbones. “Because then neither of us will be meeting anyone new, since we’re both not looking to do that.” I was trying really hard to be funny. “We’ll just sit here and drink by ourselve, since that’s the only reason we’re both here.”
“I’m sorry,” she giggled, “I didn’t mean to sound like a bitch. It’s just…” She paused and put her head down.
“Did you just get out of a relationship or something?”
“How did you guess?”
“I could just tell. I’m in the same situation. My girlfriend just dumped me, like last week.”
“I’m sorry,” she said sweetly, “you must be hurting.”
The second her drink came, I made a toast. “To two people who recently got dumped, one who happens to be a complete knockout.”
“Thanks,” she said with a big grin.
“…And then there’s you,” I joked.
The girl cracked up and we both laughed as we toasted and sipped our drinks.
Over the next round of cocktails, I found out a lot about frosty pink, whose name was Susan. She was thirty-five, she worked for an advertising agency, and she had moved here from Cincinnati four years earlier. The most important thing I found out about Susan was that she really wanted a baby! Even better, Susan told me that she was completely frustrated because she didn’t make enough money. “The bottom line,” she said, “is that I want to be wealthy.”
Now I knew I’d just hit the jackpot with this one. That’s why I wasted no time and decided to get right to the point. After a few martinis, it wasn’t hard to be blunt. “Can I be honest with you, Susan?” I slurred.
“Sure.”
“No, I mean brutally honest.”
“Please…”
“I need to have sex with someone.”
The look on Susan’s face transformed so quickly it was frightening. She looked like she wanted to kill me.
“This drink is about to be thrown in your face, so I would get up pretty quickly if I were you,” she said in a very low voice.
I pleaded with her, “No…no…listen to me.”
Susan picked up her glass and began tilting it in position to toss it in my face.
“Seriously, Susan, listen! If I don’t get a girl pregnant in the next two months, I won’t inherit any of my mother’s money!”
“What are you talking about?”
“Look, this is serious. I have to have sex, lots of sex, until I get someone pregnant.”
She grabbed her purse off the bar and stood up to go. “Sorry, this is just a little too weird for me.”
I had to make her understand, so I stopped her. “I have a proposition for you,” I said, “If you sleep with me and get pregnant, I promise you, you’ll get rich. Plus, you’ll have a baby! This couldn’t be a more perfect situation for you.”
“What are you talking about?”
“I’m talking about millions of dollars. I’m willing to give you a million dollars to have my kid.”
Susan took a big gulp of her drink. “Let me get this straight. Did you say A MILLION DOLLARS?”
“Yup,” I said, feeling more confident than I did a minute earlier.
“So, what do we do? Start trying tonight?” she asked.
I looked down at Susan’s lap. Her legs were crossed and there was a slit in her skirt that was exposing one of her thighs. I found myself so focused on baby-making, that as nice of a thigh as it was, it was barely turning me on.
“Absolutely,” I answered. Now I knew I was in.
“So, will you give me some of it tonight?” Susan asked, throwing me a curveball.
I was confused. “What do you mean?”
“I mean, if I sleep with you tonight, I want a thousand dollars.”
Now I was a little weirded out. “Are you joking?”
“No,” she said, “If I’m going to have sex with you, I deserve to be paid.”
I didn’t know where this was headed, or what just happened here, but all of a sudden I got this strange feeling about Susan, almost like she was a prostitute. I knew I was being ridiculous for thinking this way, however, because the girl had been so descriptive when talking about her advertising position. My head was spinning, combination confusion and alcohol, but I knew Susan was my last prospect of the evening so I decided to bypass her bizarre behavior and just give things a shot.
I stood up, put my hand in my pocket, pulled out a wad of cash and counted it. “Okay listen, I’ve got two hundred fifty bucks. What do you think?”
“Can I see it?” she asked.
I handed her the money and within about two seconds, she took it, grabbed her purse off the bar, and pulled out a badge and a pair of handcuffs. “You’re under arrest for soliciting a prostitute,” she said in a very different voice than she had been using all night.
Before I could even speak, I was being handcuffed. Several bar patrons watched my arrest as Susan, now known as Officer Kay Olson of the Chicago Police Department special crimes unit escorted the suspect out of the bar. I sobered up quick, especially when we got outside and I saw the police car that would take me to jail.
“Are you crazy? I was totally set up! This is entrapment!” I yelled.
Susan, with the beautiful lips and high cheekbones opened the squad car door. “Get in,” she said.
At 6:00 the next morning, I was awakened by the faint ringing of my cell phone. I jumped out of bed, wearing sweats and a t-shirt Drew had left at my place. I wouldn’t tell him I loved him, but I was so attached I had now taken to sleeping in his clothes.
I ran around the apartment searching for my ringing phone, wondering who could be calling so early. It was either Drew or Frankie, both headed out of town today and probably calling to say good-bye or give me some last minute details. I finally located my
Blackberry
, which was hidden under a stack of unread mail on the kitchen counter.
“Hello?” I answered.
“Where have you been?” asked Danny. His voice was very loud and very urgent. “I’ve been calling you for hours!”
“I must not have heard the phone. What’s up? What’s wrong? Is it Ma?”
“No. I’m in jail.”
“What?”
“I’m at the police station at 44
th
and California. Will you come get me?” he asked.
I stood there in shock.
“And call that guy, Alan, Ma’s lawyer,” he added.
My head was spinning. Where was 44
th
and California? Where was Alan’s phone number? Most likely it was attached somewhere on the “baby for money” contract.
“Danny, what did you do?”
“Nothing. I’m innocent. I’ll explain when I see you.”
“Okay, I’ll be there as soon as I can.”
“And Jamie?”
“Yeah?”
“Bring your checkbook. You know…for bail. And whatever you do, DO NOT call Ma.”
“Gotcha,” I said, before ending the call. I stood there deciding what to do first. Call the office and tell them I might be late? I could call from the cab. And did the police actually take checks for bail?
Quickly, I took off the sweats, threw on a pair of old jeans and headed out, wondering what on earth Danny could have done to have gotten arrested. In the back of my mind, I somehow knew that the whole baby thing had something to do with it. That’s why I had a strong urge to call Ma and let
her
deal with the mess she’d created. But Danny told me not to. Plus, my baby-loving mother was probably at the airport drinking mimosas, waiting for her first-class flight to board.
The first thing I did when I got in the cab was call information for Alan’s number. Seconds after I was connected, he answered. I was shocked. I expected to get his voice mail at 6:10 a.m.
“Alan speaking…”
“Hi Alan, this is Jamie Jacobson. I…”
“Hello, Jamie, how may I help you?”
He was being extremely courteous. In fact, the way he was treating me was making me realize how much he really liked my mother. Of course, it didn’t hurt that his client was worth millions.
“Well, my brother’s in jail. Apparently, he was arrested last night. He’s at 44
th
and California, wherever that is, and I’m on my way there now.”
At this moment, I noticed the cab driver checking me out in his rear view mirror.
“Okay, Jamie, slow down,” Alan said, “First of all, do you need directions?”
“No, I’m in a cab.”
“Okay, good. Now tell me what’s going on with Danny. Where and why was he arrested?”
“He didn’t tell me anything. He just said to come get him and to call you.”
“Okay. One of my colleagues will meet you there shortly to represent Danny and to bail him out. You just get there and don’t worry about a thing.” Now I surmised that Ma was paying him well.
I thanked Alan, hung up and then realized my cab driver was lost. He proceeded to drive around for a half hour looking for the place. When we finally made it there, Danny and some guy, who I presumed was Alan’s lawyer buddy, were standing in the lobby talking.
“It’s about time,” Danny said with hostility, “First you don’t answer your phone, and then it takes you an hour to get here!”
“My cab driver got lost. Excuse me!” I replied.