Eight o'clock on the dot, Chuck reached over with a groan to dismiss his alarm, more so out of habit.

But then suddenly he sat upright, remembering he had fallen asleep on the couch last night. After Nate had returned to tell him that Little Jenny Humphrey had committed suicide by jumping from the roof of the hospital.

How did I get in bed? He couldn't help wondering as he scratched his head. And once again, he noticed that oddly enough, considering how much he had had to drink last night, he wasn't feeling hungover in the slightest.

Getting up out of bed, he heard voices coming from across the hall in Nate's room as he approached his own door.

"I know, we're just friends – you're in love with Serena," he heard an all too familiar voice, prompting him to quickly get up and go see just how it was possible.

"Hey, Nathaniel! You're up," he remarked as he burst into Nate's room without even knocking, shocked to see Jenny sitting there in the bed next to Nate, looking just how she did two days ago when he walked in on their oh so innocent sleepover.

"Hey... Jenny's actually on her way out, she just crashed for the night – nothing happened," Nate quickly tried to assure Chuck, not wanting him to get the wrong impression or think he cheated on Serena.

"Yeah, sure, whatever – can I... talk to you for a minute?" Chuck requested, confused as to what was going on.

"Uh yeah, okay – I'll be right back," Nate turned to Jenny as he got out of bed and followed Chuck out into the hallway. "Look, I swear – nothing happened!" he began to protest immediately.

"Yeah, I don't care about that," Chuck quickly assured him, looking over his shoulder, watching the doorway anxiously, as if Jenny were going to just apparate into thin air.

"Okay... then what's up? You nervous about today? Honestly, I'd be more shocked if Blair didn't show up-"

"How... how is she alive?" Chuck interrupted, still not sure how Jenny being there was even possible.

"What? Who?" Nate questioned as he looked around, noticing that Chuck was carefully watching Jenny as she made her way around his room. "Jenny?"

"Yeah..." Chuck's voice trailed as he continued to watch her. It was like watching a ghost.

"What do you mean how is she alive?"

"Last night – her and I had some words, I was depressed over Blair yet again and passed out on the couch... you woke me up a little while later and told me that Jenny had died – that she jumped from the roof of the hospital..." Chuck tried to remind him.

"What?!" Nate exclaimed, trying not to be too loud, afraid that Jenny might overhear and get creeped out. "Why would I tell you that?"

"I don't know but that's what you told me," Chuck informed him. "And then you left to go back to the hospital and I fell asleep on the couch again only to wake up this morning to hear you two and see her alive," he continued. "Does anyone know she's here?"

"I... I don't know...?" Nate answered, unsure of what his answer should be. Rufus, Lily and Eric would probably not be too happy if they knew Jenny had spent the night with him and Serena and Dan would both be livid as well. "I don't think so...?"

"I know!" Chuck declared as the thought came to him. "She's hiding out, isn't she? She faked her death so she could get out the mess she caused these last few days and start over fresh somewhere else, right? I can believe that after everything you're helping her..." he went on.

"Mess she caused? What are you talking about? You mean by tipping off William so he could evade the police?" Nate questioned, trying to follow what Chuck was saying.

"No I mean the mess she caused between you and Serena... which in turn affected Dan and Vanessa... and then Blair and I..."

"Dude, I have no idea what you're talking about – are you sure you're feeling okay?" Nate wondered as he put a hand to his best friend's forehead. "You do feel a little warm..."

"I'm fine," Chuck grumbled as he swatted Nate's hand away and walked away in a huff to get some coffee. Maybe once he had some caffeine in him things would start making sense.

As he sat down to drink his coffee a little while later he reached for the day's newspaper and noticed yet again that it was the same paper from 2 days ago.

"Nathaniel!" he barked from the kitchen, prompting Nate to peek his head from around the corner.

"What?"

"What's with this newspaper? Have we seriously not gotten one in days?" he questioned as he held the offending paper up in view, making a note to speak with the front desk about what was going on and why his daily paper wasn't getting sent up.

"What are you talking about?" Nate asked yet again, this time now growing annoyed.

"Knicks beat The Heat 89-86? That's from Friday," Chuck pointed out.

"Yeah, sounded like a helluva game – kinda annoyed I missed it for the charity thing," Nate remarked.

"Which this paper also has coverage of... saying it was last night," Chuck hissed. Now he was annoyed.

"Chuck, the charity event was last night," Nate argued back.

"The charity event was on Friday – last night was Sunday. Today is Monday," Chuck corrected him.

"Today is Saturday," Nate spoke matter of factly.

"No it's not," Chuck continued to argue.

"Yes, it is," Nate held firm.

"Tell me, has Dorota had her baby yet?" Chuck asked, knowing that would determine for him just what was going on.

"I don't know – I don't think so? She should any day though if she hasn't already..." Nate responded as he tried to recall. Chuck sighed in frustration as of course Nate wouldn't be able to tell him for sure.

Just then, Chuck's phone chimed that a notification had gone off.

"Again?!" Chuck remarked in surprise as he read for the third time now the Gossip Girl blast about Serena and Humphrey waking up together in Dan's bed. "I think Gossip Girl is broken," he stated as he sat the phone back down.

"God I hope so," Nate sighed in disappointment as he too read the blast. "I guess I should go and find out what actually happened," he decided as he retreated to his room.

Curious, Chuck decided he'd go and try to see Blair. Maybe seeing her would help make some sense.

"Charles, how lovely to see you... can't say we were expecting to see you," Eleanor remarked the moment he stepped off the elevator and into the Waldorf penthouse.

"Lovely to see you too, Ms. Rose - can you tell me is Blair still here?" he asked her, getting straight to the point.

"No, actually, she's out. With Dorota and some good-looking young man from Columbia... she said something at breakfast about avoiding The Empire State Building and how Affair to Remember was on last night and it gave her nightmares..."

"Yes, yes... avoiding The Empire State Building... anything else?" he pressed her further, growing more and more impatient.

"Well she just left not too long ago... I imagine she went to the park," her mother spoke after thinking for a moment. "Why? Is something the matter? Has something happened? You seemed rushed, Charles."

"I am," he confessed as he pulled out his phone and texted Arthur to have the car ready. "Dorota hasn't had her baby yet?"

"No, Charles, she hasn't... but we all wish she would already! Dorota is far too pregnant right now to be of any help," she quipped in annoyance. "Why are you in such a hurry? Does it have anything to do with saving your relationship with my daughter?"

"Something like that," Chuck admitted as he shut off his phone screen after reading the confirmation from his driver.

"Well if I might say, I'm glad to see you're out and about again," she spoke once more, causing Chuck to turn back towards her, a puzzled expression on his face. "I know you and my daughter have been at odds ever since Dorota's wedding for reasons she won't tell me, but despite whatever happened... I know she still loves you and has been concerned for you regardless. If you're trying to win her back – I suggest you do so soon. That young man from Columbia she's been seeing is quite the charmer however I know he won't make her happy for long," she encouragingly nudged him before she went about her way.

He had to admit, it was nice that at least someone was rooting for him these days.

Once he got to the park, he quickly spied her by the duck pond, with a clearly pregnant Dorota, bread and Columbia Cameron in tow. He had to chuckle as the guy was clearly nothing more than an accessory she was toting around to rub in his face. He wouldn't be surprised if she purposely tried to make it work with the guy just to spite him. He knew from her years of dating Nate that sports bored her to no end and clearly the guy was an athlete through and through.

Keeping his distance and a low-profile, he followed them out of the park and spied them stopping by a news stand and hot dog vendor. Again, he he couldn't help a laugh from escaping as he not only witnessed Dorota ordering a jumbo dog with everything on it, but the look of disgust Blair shot her and the look of horror she wore when her date had the audacity to offer one to her. She almost looked relieved when she got a phone call. He watched her intently from his limo sitting across the street, she almost looked excited when she got off the phone, something having entered her mind, only for her to quickly change gears as she spied the front of a tabloid a man nearby had held in front of her.

"Follow them," Chuck ordered to his driver as he witnessed the three of them pile into the back of a waiting town car. Curious, he looked back to the newsstand just to see what it was on the tabloid that had rattled Blair so easily. When he saw it was a headline about The Empire State Building he lost it. She couldn't avoid his ultimatum no matter how much she tried.

"Is here okay, sir?" Arthur questioned as he slowed the car to a stop. Chuck noted they were in Brooklyn, just outside the Humphrey loft. "If we go any closer we risk being spotted," he informed him as he waited for an answer.

"Here is fine," Chuck decided as he watched the scene unfold.

Blair had rushed inside, to chew out Jenny Humphrey, no doubt, while her date and Dorota loitered outside in the alley. A minute had barely passed when Rufus and Dan both showed up. After Cameron had motioned up towards the loft, Rufus said something to Dan before hurrying on in, leaving Dan to chat with Dorota who began to show off what appeared to be her sonogram pictures.

He smiled when Blair reappeared a minute or so later, promptly smacking Dan as she rejoined her party and proceeded to get into it with him, most likely laying into him for getting involved with Serena and interfering in her relationship with Nate.

They had both been rooting for Nate and Serena, much like Nate and Serena had been rooting for them. Nate and Serena made just as much sense as him and Blair did – it was fate, they were destined to all be together, yet how that would be achieved successfully and for good was something they all had yet to figure out. He could only hope they were getting closer. That is... assuming this day would ever end for him.

He noticed Blair looking off in the distance after something Humphrey had said to her, turning back with a smile on her face and a look of relief. Looking where she had, he noticed it was The Empire State Building.

"You can't avoid fate, Blair," he spoke to himself with a smile of his own.

She had just sent her date away for good in a yellow cab and was ushering Dorota back into the town car when he noticed her, Dan and Dorota all froze. He started to get a little concerned but was relieved when they all quickly got in the car.

"Arthur, we need to make a quick stop by The Empire and then to The Empire State Building – the plan's back on," he barked as the car quickly began to head off.

This is it, he thought. She's going to be there.

Only she wasn't.

Chuck waited, getting there just in time, despite the detour he made to The Empire to retrieve the ring as well as a bouquet of peonies.

Yet she still didn't show up.

Irritated, he checked the time on his phone.

7:01

WHY?! He screamed in his head.

He watched her carefully today. Everything that happened... he knew she was coming.

Or so he believed.

Maybe he just desperately believed what he thought had happened when it had really been something different? Maybe something happened? Did Dorota have her baby? (again?). He found it hard to believe though that something like that would happen and Blair wouldn't have texted him, letting him know she was going to be late. She was never late when it came to things that mattered to her.

Resigned to the idea that he was wrong and it wasn't going to happen, she wasn't coming, he left. Brokenhearted and rejected.

Not wanting to be alone tonight, he picked up a pair of escorts in the hotel lobby and brought them upstairs. Needless to say, he was a little surprised to find Jenny Humphrey sitting on his couch, waiting alone.

"I was just waiting for Nate," she quickly offered up as she saw Chuck walk in through the foyer.

"Ladies, go on in, make yourselves at home," he instructed the girls towards his room as he proceeded on past Jenny to the bar.

"You know he's probably with Serena, or at least trying to mend things with her," he nonchalantly spoke as he selected a bottle of champagne and grabbed a trio of glasses. "And honestly, I would suggest you leave anyhow before things get awkward," he remarked as he began to make his way towards his bedroom.

"Things not work out with Blair?" Jenny questioned as she watched him, her question forcing him to stop.

"Take a wild guess," he grumbled as he hated being reminded of how his grand romantic gesture once again failed.

"Sorry..." she spoke, not really knowing what else to say to Chuck as they had never been close. "If it makes you feel any better, I'm trying to forget some stuff too," she offered up.

"Yes, well... if you don't mind, I'd prefer my own methods of forgetting compared to anything you could possibly come up with," he snarked as he retreated to his room.

"Chuck?" he heard voice calling out sometime later. "Chuck?" she called again, her voice getting closer as he sat up in the bed, a naked escort tiredly relaxing on both his sides.

"Shit..." he mumbled as he tried to think fast a way out of his current predicament. Jumping out of the bed, almost tripping over one of the girls, he quickly grabbed his silk boxers and pulled them on before proceeding to throw the duvet over the girls, trying to at least cover up their nakedness.

"Chuck?" she called out once more, this time turning the bedroom doorknob. He knew he was screwed.

"Are you in... here...?" her voice trailed as she stepped into the room and quickly surveyed the scene she had walked in on. "Unbelievable!" she exclaimed. "Just... unbelievable!" she declared once more before stomping back out.

"Blair, wait!" he called after her, quickly grabbing his robe and tossing it on, closing the bedroom door behind him as he chased after her. "Let me explain!"

"What's there to explain, Chuck?! Clearly I was wrong," she huffed as she impatiently tapped her foot, wishing the elevator would hurry up.

"I thought you didn't love me anymore! All day, I followed you around... every sign pointed otherwise and I was sure you were going to show up-"

"You followed me?"

"Yeah... and like I said, I was so sure you were going to show up but then when you didn't... I don't know... I thought I had misread everything I saw today, that I was wrong, you really were done with me... I didn't care if I lived or died! I just wanted... needed to feel something, anything other than what I was feeling," he attempted to explain to her as the elevator finally arrived.

"Dorota's water broke – that's why I was late!" she snapped as she stepped onto the elevator.

"Blair, I'm sorry!"

"Save it, Chuck. I'm done."

"You could have texted me!" he called after her as the doors began to close.

"This day never happened!" she yelled back, tossing the familiar bouquet of peonies at his feet just before the doors shut.

Chuck sighed in defeat as he gently beat his head against the wall. Reliving and failing today didn't hurt as much as it did the first time, however it still wasn't good.

"Hello, faithful friend," he commented to his decanter of scotch once he reached the bar and helped himself to a drink.

It was going to be yet another night of drinking away the pain.

At least this time he had some entertainment, even if he wasn't fully in the mood anymore.

AN: Thank you to everyone who has read/reviewed/followed/favorited this story! I'm glad to hear that most of you are familiar with Groundhog Day and are excited to read this twist on it!=D

Keep in mind, Chuck still hasn't fully figured out just what the hell is going on nor the slightest idea on how to try and fix it.

Any guesses on what happens next? Leave me a review and let me know!

Until next week, XoXo!