Serena was let go after another day, she needed some time alone, so she sent Blair home, or to Chuck's bedroom. Serena went for a walk by herself. She inhaled, then exhaled, fresh air. Then she listened, silence, in New York City, that's impossible. Then she heard laughing, she knew it couldn't stay for long. This man closed his phone. He looked at Serena like she was goddess. "Hello," she said softly.
"Hi," he said.
"I'm Serena, who are you?" she asked curiously.
The man gulped. "I know who you are—" he muttered. Serena scrunched her face with weirdness. This guy was kind of creepy. He shook his head out of the hypnotist. "Dan, Dan Humphrey. I go to Saint Judes, you've never seen me?" he asked.
Serena shook her head. "No, sorry." They started talking for a while and Serena turned out to actually kind of like this guy. He was funny, nice, and attractive. Short brown hair, and had a brown leather jacket. Stylish.
"Well, I should be going," he said pointing his way to the bridge that led to Brooklyn.
Serena nodded and waved. They both turned back to back and started walking their separate ways, until Serena had an idea. She turned back to him and shouted, "Humphrey!" He turned immediately. She walked closer to him. She could do this, right? Of course, she hasn't seen Nate in three days, no call, no letter, nothing. "I know this is weird since we just met, but my friends are having a wedding in Jamaica, and that's pretty far, but we're leaving tomorrow, Friday until Monday, so what do you say?" she asked.
He nodded. "The Sheppard's wedding?" he asked. Serena nodded. "My dad was invited to it; we were going to go anyways. So, yeah I'll go."
"You guys were invited?" Serena asked shockingly. Dan looked down. "Oh I didn't mean for it to sound bad, it's just—" She was stuck.
"I live down there and they live up there? Yeah, well, my dad has an art gallery and Don Sheppard has been going there forever," he explained.
Serena nodded. "Sorry for sounding so bad, I hope you'll still come to the wedding with me." Dan nodded. "Okay, well, I guess you should be going," she reminded him.
"Yeah, bye," he said as he leaned in and hugged her. "I'll—I'll see you tomorrow in Jamaica." And he walked off.
'I'll see you all in Jamaica. Cannot wait for the Sheppard's wedding.'
The next day, Blair, Chuck, Serena, Lily, Bart, Eleanor, and Anne got on the plane to go to Jamaica. Blair sat next to Chuck, Lily next to Eleanor, Serena next to Anne, and Bart by himself. Serena could hear Chuck and Blair kissing each other; this was them doing it quietly, too. They were trying to be quiet so their parents wouldn't hear, but if Serena could hear them, two rows away, their parents could probably hear them. Anne turned her head towards Serena. "So, have you talked to Nate lately?" she asked in her sweet voice.
Serena smiled, and shook her head. "No, where did he go?" Serena asked. She was actually very excited to hear the answer to this question. Nate didn't tell her anything.
Anne looked shocked. "Nathaniel didn't tell you?" she asked. Serena shook her head. "That's weird; he couldn't stop talking about you for ages. But he went to Jamaica earlier on his boat. I asked why he wasn't going with you and he just slammed the door. What happened?" she asked.
She shook her head. "Nothing important, I'm hoping we'll settle it in Jamaica."
"Chuck, do we have a room together? Or is it Serena and I and you…" Blair asked, not knowing who Chuck would be sharing a room with.
He turned to her. "Nate?" he said. Blair raised her eyebrows in shock. "Yeah, he's there, he sent me an email earlier. But no, it's you and me."
She turned to Serena. "Who will she be sharing her room with?" Blair asked curiously. Chuck smirked. "Nate?! No, no, no, I will not allow it. Who would be stupid enough to put her in a room with him?!" she shouted. Then she turned to Serena, good, she was chatting with Anne, not paying attention to her and Chuck's conversation about her. Blair turned back to Chuck to see an even bigger smirk on his face. "You put them together?! You ass! Why would you do that to them?!" she said, a bit louder.
"So they could work it out. I made the rooms non-switchable, so they'll be stuck with each other," Chuck informed her.
Blair scoffed. "Chuck that is the worst plan you've ever made." He looked upset. "But it just might work. Okay, but if Serena or Nate comes in our room asking us about it, what shall we say?" They planned and planned the whole ride there. They were turning into the old, scheming Blair and Chuck.
They all got to the hotel in Jamaica and the first thing Serena was to do was to go to room 65, Dan's room. Of course, she didn't go straight there, she went to get her key and check what room she was in, room 43. She used the elevator because of all the suitcases she had with her. Serena walked into her room to see stuff already there; she got freaked out, until she saw someone's name on it. Nate Archibald. Seriously, they put her in the room with her ex boyfriend who didn't know she had gotten raped? That's wonderful. Serena dropped all her bags and went upstairs to room 65. She knocked on the door threw times. "Humphrey open you door!" Serena screamed. He did after another knock. "Hey there," she said, obviously impressed. Dan was wearing a tux, but without a tie and open collar. He looked like Nate when they had their water fight. She shook her head, no she cannot think about Nate now, she's just going to go downstairs and talk to the people working here.
"Umm, I'd really like to talk to you, but I have to get ready for the wedding," Dan told her.
Serena nodded. "Okay, I guess I'll come here twenty minutes before we're supposed to leave." He nodded and Serena left. She was going down to the front counter to talk to the person about Nate and her living arrangement. Serena got there just to see a line up, and to see a very familiar body and back of the head in the front of the line. Serena started walking up to the front of the line, not caring that people were yelling at her. "Nate?" she said in a calm voice.
Nate turned to see her wearing shorts and a t shirt; she looked beautiful. Nate had underestimated her looks when he was remembering her on his boat. "They put us in the same room," he said. He still hadn't forgiven her for sleeping with another guy while they were dating.
The woman at the counter cleared her throat to get their attention. "I'm sorry sir, but it says here that you may not switch your rooms. No exceptions," she said in a high pitch tone.
Nate shook his head in disappointment. "What if she had a deadly disease that I could easily catch?" he asked.
"Well, does she have a deadly disease that you can easily catch? Because if she did, she should be in the hospital," she told him.
Nate took his key and left the counter. Serena smiled and waved at the woman at the counter. Serena walked into her and Nate's room without Nate. He went to talk to Chuck and Blair. He burst into the room while they were kissing. "I cannot believe you guys did this!" he screamed.
"Well hello Nathaniel, nice to see you too. But we are dating, I think it's necessary," Chuck said in his smug voice, referring to the kissing.
Blair looked at him with a death stare, and then looked back at Nate, he was shaking his head. "You put me in a room with Serena? Are you serious?" he said harshly.
"Nate, we didn't do that—" Blair started.
"No Nate, we did do that." Blair looked at him again. "He should know about Serena, Blair."
"What about Serena?" Nate asked worriedly.
Blair nodded and stood up. "You broke up with Serena when she 'slept with someone else' correct?"
"Blair, he already knows this, just get to the real reason why she was crying."
She turned back to Nate and looked straight into his blue eyes. "Nate, she didn't sleep with someone, someone slept with her." Nate looked confused. "Someone drugged her again Nate! And you wouldn't let her speak! Someone raped her and the boyfriend she loved had just broken up with her. Life sucked for her, she probably felt like dying." Nate looked more worried. "Then she hit the ground and stopped breathing." With that Nate ran out of the room and started running towards his room shared with Serena. He could hear her laughing, why was she laughing by herself? He got four feet away from the room just to see Serena being escorted out of the room with a guy who looked very familiar. Maybe he went to his school, probably did. Nate quickly jerked his head down so Serena wouldn't see him. It's over.