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Authors: Jackie Pilossoph

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BOOK: Jackpot!
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“So what are you going to do?”

“Well, actually, I broke up with her.”

I put my head down as I thought about how disgusted I was in myself. I’d called Courtney that morning and told her I couldn’t see her anymore.

“I really like you, it’s just that I’ve got major issues and I need to deal with them.”

Her response had been like taking a bullet. She’d said, “It’s because I can’t have kids, isn’t it?”

“No, I swear!” I’d defended myself.

“Danny, you don’t have to explain anything to me. I’m really sad about this, but I’ll be okay. I get it.” She finished with a sad chuckle, “You’re holding out.” Then she hung up and I’d wanted to shoot myself.

“So I guess I’m choosing money over love,” I said to Jamie.

“You don’t have to,” she said, pity in her eyes.

“Yes, I do,” I replied, “I want to have money. I’m thirty-four years old and I live in a shoe box. I’m tired of struggling. I’m tired of dressing up as a fucking pretzel on the weekends. As far as women, it never works out with them anyhow. So I’m picking the sure thing. Cash.”

When I said it never works out with women, Jamie knew exactly what (or I should say, who) I was talking about; Jillian, the only girl I’d ever loved.

I met Jillian while living in New York. It was at a wine-tasting event. Actually, Jillian was a guest at the event and I was a wine pourer. She tapped me on the shoulder and asked me for a pour of the 1998 Blackstone Cabernet I had in my hand. When I looked at her I went numb. She was so cute! I could tell by the look on her face that she wanted more than just a glass of wine. So I asked her for her phone number.

Typically, I’d have asked her to stay until my shift was over with the intent to take her home with me. But I wasn’t in a hurry with Jillian. She seemed sweet and pure. Shit, how could she not be? She was a pre-school teacher! I was sure she’d never had a one-night stand in her life. So, as unusual as it was for me, I chose to ask her out on a date, not caring if we were going to have sex afterward.

We ended up going out and having a great time. At the end of the night, all I got was a light peck on the cheek, and that suited me just fine. We went out for the next five nights in a row, and every night I got a peck, until the fifth night. Jillian took me to bed. I finally got to touch this beautiful girl. And to my surprise, it wasn’t at all what I expected. It was better. I was in love with her. I knew it right then.

We dated for a few months. Things couldn’t have been better. Then, like an unexpected hurricane, Jillian’s old boyfriend came back into the picture. The guy started pursuing her, calling all the time, sending flowers every other day, and showing up at her place, even when he knew I was there. In my opinion, the guy was a stalker and Jillian should have called the cops and had him arrested. She didn’t, though. Jillian didn’t see her ex as a psycho. She was actually touched by all his efforts. I couldn’t believe how she kept defending him.

“Please don’t hate him, Danny,” she would say, “He was really confused when he broke up with me. He’s different now.”

Speaking of “different now”, that’s what I was starting to think about my girlfriend. She had no backbone. The old boyfriend had dumped her a couple years back and married some other girl. Now he was divorced and back to claim in his words, “the one who got away.” Jillian was taking his side more and more, and things between us were becoming rocky.

Finally, one night when we got back from dinner, the guy was waiting in her lobby, holding up a big jam box over his head like John Cusack did in the movie, “Say Anything.” The second he saw Jillian, he put the box on the doorman’s counter for a second, pressed play and put the box back on his head. The song, “In Your Eyes” began to play. I couldn’t believe it. The doorman just sat there, and Jillian began to cry. Apparently, “Say Anything” was both Jillian and the guy’s favorite movie. All I could do was walk away. The sad part was, Jillian and her ex didn’t even notice me leaving. To this day, I can’t even look at John Cusack.

When I moved back to Chicago, I was still heartbroken about Jillian. And looking back, I think I made a subconscious decision to take my pain out on every other woman in the world by keeping them at arm’s length, never allowing myself to be vulnerable again. Yes, with women I was charming and sweet on the surface, but when it came to any kind of commitment, or being someone any girl could depend on for anything other than a good time under the sheets, I had mentally checked out.

Except for Courtney. She made me want to be one of the good guys again. Courtney had changed me from the guy who didn’t care to the guy who cared deeply. But now, like my mother’s sudden physical transformation, I’d quickly changed back to the coward.

“Look, Jamie, we’re not talking about a few hundred dollars. This is EIGHT MILLION BUCKS. Yeah, I like this girl, but I don’t even know her. Is she really worth risking that kind of money?”

“Only you can answer that,” said my sister.

“My mind’s made up. I made a few calls and I have three dates lined up this week. I don’t want to do it, but I am.” I put my head down in shame and added, “Just so you know, I hate myself right now.”

All of a sudden, I heard a guy shout, “Jacobson?” I looked at the propped open door and there stood a guy holding a clipboard.

“That’s us,” I answered.

“Delivery from Macy’s,” said the guy, “I need a signature before I bring it in.”

“I’ll sign,” said Jamie, standing up, “My mother’s on the phone in the other room.”

A few minutes later, two guys were coming through the door. “Hold her steady,” I heard one delivery guy say to the other, “I’ll back in.” When I got a view of what they were bringing into Frankie’s condo, my jaw hit the ground.

“Wait a minute,” I shouted, “A woman with no grandchildren bought a crib?”

Jamie shouted bitterly, “It’s against all principles of Judaism to bring a crib into the house before the baby is born!”

“Or before it’s conceived!” I added.

My sister sat there, a hopeless look on her face. Then she asked me, “Does food poisoning really only last twenty-four hours?”

Chapter 14

 

I found myself checking my
Blackberry
for texts or missed calls all day. ‘Would he call?’ I kept wondering. Other than the sudden onset of food poisoning, our date had been great. So, of course he’d call! But When? I was feeling quite desperate to hear from him, and I hated to admit it but it wasn’t all because I needed to have his baby stat.

When I got home from Ma’s place, my phone finally rang and I figured it was Frankie calling to make sure I got home okay. It was a given that she checked in with me every time I left her place, just to make sure nothing happened in the ten minutes it took to get from her condo to my apartment. I looked at my
Blackberry
. “Unknown Caller,” it read. That’s how I knew it was Frankie.

“Hi Ma, I’m home,” I answered the phone.

The caller disguised his voice to sound like a high-pitched older Jewish woman with a heavy New York accent. “Thank God honey. I was worried!” said Drew.

I giggled. “What’s with the New York accent?” I asked him, “We’re from here.”

“I was just trying to do the Jewish mother thing,” Drew said in his normal voice.

“Other than the accent, not bad,” I responded, “She really does sound sort of sound like that.”

“Maybe I need to meet her to see for myself.”

“You want to meet my mother?”

“Why not? I’ve always heard that girls eventually turn into their mothers.”

“Well, please shoot me if that happens.”

“She can’t be that bad,” he replied.

I couldn’t help but think that if he knew about the baby scheme, he’d retract his statement.

“So, how do you feel?” I asked.

“I’m okay. I pretty much threw up all last night and this morning, but I think it’s all out of my system.”

Danny’s fake food poisoning theory flashed through my brain.

“So, are you free tonight?” he asked, “Want to get together?”

“Sure.” My smile was so wide I was afraid he’d be able to see it through the phone.

“Pick you up at eight?” Drew asked.

“Okay,” I said, dashing to my closet to start pulling clothes off hangers so I could throw prospective outfits onto the bed. “Do you know where I live?”

“What do you think?”

“Yes.”

“See you soon,” he said before ending the call.

I stood there for a moment and had a silent argument with myself. ‘I’m using Drew and I hate myself for that.’

Myself answered, ‘Yeah, but you’re going to be loaded!’

‘But he’s a really nice guy, and he
really
likes you.’

‘You’ll pay him off,’ myself answered. And that was how I rationalized for the moment that seducing Drew and having his baby was okay.

I ripped off my clothes and jumped in the shower. It was already 6:40, so I had an hour and twenty minutes to make myself look like someone Drew wanted to have sex with. Sad, but that was reality. The words con artist, manipulator and deceitful swindler were coming to mind, but I had to block them out. The words
eight million dollars
meant a lot more right now.

In the shower, I began to think about what was really going on, which was how much I was enjoying my potential sperm donor’s personality. After all the years together at work, it took my mother’s crazy dream to buy grandchildren to get me to go on a date with Drew. Ma was indirectly making me give him a chance, and part of me felt thankful to her for that.

On the other hand, who was I kidding? What were the odds that Drew and I would actually work out as a couple? Relationships with men never seemed to pan out for me. In fact, I wasn’t sure if I’d ever been in love. I barely knew John when we got married, and Max, that was
security
, not love. I didn’t have a lot of faith in myself when it came to men. That was the sad, sad, secret I kept to myself. John had really done some damage to me and my self-esteem, and I wasn’t sure I’d ever have the guts to trust someone ever again.

I heard my phone ring, but I couldn’t get it since I had shampoo in my hair. I knew this was Frankie’s call, and I felt like telling her she should be more worried about her daughter’s mental state, rather than if she made it home safe. Ma was turning me into a neurotic, conflicted mess.

After the whole hair process, which meant towel drying, applying two different kinds of hair gel, blow-drying, flat-ironing, putting hair crème on the ends, and spraying enough hairspray to become a fire hazard, I decided on a slinky black dress and silver sling-backs. I went heavy on the make-up but light on the perfume, because I didn’t want Drew to think I was trying too hard. Around my neck, I wore a circular emerald, which ironically was given to Ma by my dad, thirty-some years earlier. Frankie had given it to me for my birthday, right after I got divorced. She told me that of all the things Dad gave her, this was the most special.

The story behind the necklace was that my parents had had a big fight about something really silly, but it was the first time they’d ever been so mad at each other that they didn’t speak for a couple days. Ma told me that even though she knew she was right, she decided to give in and make amends. So she went out and bought her husband an “I’m sorry” card and left it on his pillow that night.

After my dad read the card, he apologized as well. They hugged and kissed and everything was back to normal, even though according to Ma, she had compromised her opinion to make peace. The next night, when Frankie went to bed, she noticed a tiny box lying on her pillow. She told me she was shaking while she opened it. Inside was the necklace. Dad told her he gave it to her to show how much he appreciated her willingness to make the first move to make up.

Ma told me that the necklace symbolized how much she and Dad meant to each other. So here I was, wearing this beautiful and valuable keepsake on a date I was going on for the sole purpose of tricking a guy into knocking me up. The necklace really was beautiful, but I wondered if I could hate myself anymore than I currently did, and if I was even remotely good enough to wear it.

BOOK: Jackpot!
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