Chapter 31

Chapter 31

“Serena? It’s Jenny. Can you come over? I’m having a major fashion crisis!” Jenny hung up the phone and went back to her closet. She searched the racks hopelessly. I have nothing to wear! was the only thought running through her mind as she pulled out random articles and tossed them aside carelessly.
When Jenny heard the knocking of the front door, she raced to answer it. “Thank goodness you’re here!” she exclaimed. “Serena, I have absolutely nothing to wear, and my date with Oliver is in an hour! Please help me!” Serena laughed at the pleading in J’s voice.
“Jenny, didn’t we go shopping like two days ago?”
“Yes, but none of that stuff is good enough! Oliver is like the picture perfect Upper East Sider!”
“Only less scandalous,” Serena added quietly, laughing.
“In any case, I really need to impress him! He won’t expect me to show up in some $20 blouse from Macy’s!”
“What’s wrong with Macy’s?” Serena asked, frowning, as she followed Jenny to her room.
“Everything, compared to the clothes his previous girlfriends have worn!” Jenny sighed as she flopped down on her bed. “Serena, what am I gonna do?”
“Well, I think you’re gonna stop moaning and try on this fabulous dress I bought for you yesterday.” Serena smiled as she reached into the shopping bag she was carrying. Jenny gasped as S pulled out a hot pink strapless Waldorf original. The gown looked like a prettier version of the gold dress Jenny wore the night of Blair’s sleepover.
“Blair and I went shopping, and we stopped by her mother’s boutique. Blair said the colour was a little dated, as in a few months ago, but I bought it anyway. I thought you wouldn’t mind.” Serena smiled as she handed the dress to Jenny. “So, what do you think?”
“Oh, Serena! It’s… it’s gorgeous! Thank you so much!”
“Don’t mention it. Oh, but you might want these, too.” S pulled out a matching pair of pink heels.
Jenny was overcome with joy. Screaming, she enveloped Serena in a huge hug. Laughing, S hugged back.
“Now you get ready. Oliver’s gonna be here soon, and you still don’t have your makeup done.” Serena smiled as she began to leave the room.
“Uh, Serena…” Jenny called after her.
“Yeah?”
“You wouldn’t happen to have a Sephora kit handy, would you?” Jenny smiled shyly. Grinning, S pulled a stuffed makeup bag out of her purse. She tossed it to Jenny.
“Here. Knock yourself out.”
After Serena had left, all Little J could do was hop around the room, ecstatic over what S had done for her.

“Oh, wow,” Oliver said, gaping at Jenny as she arrived outside the restaurant. “You look… amazing.”
Jenny smiled. She didn’t want him to pick her up from home and see where she lived, so she had asked him to meet her at a club in downtown Manhattan. “Thank you. You don’t look too bad yourself.”
Oliver was in a navy blue dress shirt and dark jeans. His amazing green eyes glittered at the sight of her. Jenny looked him all over, wondering why he looked so vaguely familiar. Suddenly, she realized it. Oliver looked very much like a younger version of Nate.
Shaking the thought out of her head, Jenny linked arms with Oliver and walked into the restaurant.
“You look so good,” Oliver told her, smiling, once they had sat down. “Pink is your colour.”
“Yeah, well, I do like pink,” Jenny said, in a failing attempt to be funny. ‘I do like pink’? What am I, a four year old girl? Jenny sighed at her stupid remark while Oliver just looked puzzled.
“Um, yeah,” he said. “I’m sure you do.”
“So, uh, anyway,” Jenny said quickly, desperately trying to change the subject. “Blair told me you’re the captain of the debate team. What’s that like?”
“It’s interesting,” Oliver replied, taking a sip from the drink the waitress had just brought him. “Even though my dream is to study social sciences, I was always interested in being a lawyer, so I joined the team to improve my skills.”
“Wow. But I also heard you play lacrosse?”
“Yup.”
“You know, I didn’t expect the captain of the debate team also to be a sports buff.” Jenny cringed at her own use of the phrase sports buff.
Oliver laughed. “Hardly. I just play lacrosse to stay fit. I’m really more of an academic. But what about you? Do you play sports?”
“Well, no, unless you count shopping as a sport.” Jenny laughed nervously as she stirred her drink with a toothpick. Oliver studied her face, and then let out a strained laugh.
The evening went on in a similar way until it was late enough for both of them to call it a night. As the two walked outside, Oliver asked, “Do you need me to call you a cab or something?”
“Oh no, I’ll be fine. I’m sure the pink stretch limo will be here soon.” Jenny smiled at Oliver, trying to read his face to see if he got the joke. He just stared at her for a moment, and sighed.
“Jenny, I have to be honest with you. I don’t like stereotype girls. You know, the kinds who traipse around in designer shoes and forty-dollar lip gloss. I don’t care about that stuff. I like girls who are confident and don’t feel like they need to buy their way into society.
“That’s why I don’t date the Blair Waldorfs of the world. I mean, no offence to Blair Waldorf, but I find those girls shallow and superficial, not to mention insecure. I want to be with someone for who they are, not who they wear.” Oliver tried to make eye contact with Jenny, but she was just staring at the pavement below her. She could feel tears welling in her eyes.
“Jenny,” Oliver said, this time more gently, “Who are you?”
Forcing herself not to cry, J looked up at him. She swallowed, and took a deep breath in. “I’m Jenny Humphrey, and I’m a freshman at Constance Billiard School for Girls. I’m always trying to fit in with the girls at my school, but I just can’t because I’m not like them. I listen to the Spice Girls and shop at thrift stores, and the only reason I’m wearing an Eleanor Waldorf original tonight is because a friend bought it for me. I couldn’t afford it if I saved up for five years.” Sighing, Jenny felt a tear slip down her cheek. “I’m Jenny Humphrey, and I’m a Brooklyn girl living in an Upper East Side world.”
Smiling softly, Oliver wiped the tear from her cheek. “I knew you weren’t yourself tonight,” he told her quietly. “But I always want you to be yourself. You don’t have to pretend to be somebody else just to impress people. Sometimes the best thing is just to be honest and true.”
Jenny wiped her eyes and looked at Oliver. “I was afraid that if I told you who I was, you wouldn’t give me a chance.”
“You should have told me. I wouldn’t have judged you.”
Still sniffling, Jenny smiled slightly. “Are you judging me now?”
Oliver smiled back. “Well, now that I know that you’re an actual human being with feelings, I don’t have to.”
Oliver placed his hand gently on her cheek, and kissed her. Jenny felt happy to be in that perfect moment, staring into his warm eyes, feeling his gentle breath on her lips. It was like something out of a fairy tale.
Jenny hugged him, not needing to say a word. After a few minutes of silent cuddling on the sidewalk, Oliver called her a cab.
“Take this gorgeous girl home,” he said to the cab driver as he helped Jenny into the back. Smiling, Jenny told the driver to go to Brooklyn.
She said goodbye to Oliver just before she shut the door, and watched him through the window as the cab began to pull away.
Leaning back on the seat, Jenny sighed. For once in her life, she felt proud to be from Brooklyn.