Love is a crazy thing. People fall so quickly in and out of it. Hearts are easily broken and feelings are often hurt. This week was all about Gossip Girl's two favorites things: breakups and hook ups. And there were plenty to go around. Seemed like everyone was either macking it or hacking it.

Chuck Bass always had a penchant for booze and women. So when he decided to follow his father's footsteps in the family business, it was no surprise he wanted to invest in Victrola, a burlesque club. The girls might be half naked and dancing on a stage, but, no, this was not a strip club. Rather, and I quote, "A respectable place where people...can feel free to let loose, no judgment, pure escape." Nonetheless, Blair Waldorf was Chuck's biggest ally. She thought his idea had franchise potential and was pretty smart. Now, the only person to get on his side was his father, Bart Bass. Bart was one of the biggest tycoons this side of the Hudson. Bart's story was one of rags to riches. Unlike the other Upper East Side millionaires, Bart was not born into this world. He worked his way to the top. When Chuck brought Bart his business proposal, he was ecstatic. Bart had been waiting years for Chuck to show interest in something besides partying. He told his son he would love to check the place out and see if it would make for a good investment property. Unfortunately for Chuck, when his father showed up at Victrola he was in a pretty uncompromising position. Chuck was at the bar feeding cherries to a half dressed dancer sitting on his lap. He totally did not scream business professional. Bart argued this was just another excuse for Chuck to be around liquor and women. There was no way he would pour hundreds of thousands of dollars into this place. As Bart left, Chuck followed him outside and watched Bart get into a limo with a young, sexy Asian woman. Hmm, wasn't his dad supposed to be dating Lily van der Woodsen? Once a womanizer, always a womanizer. Looked like the pot calling the kettle black had young Bass boiling over. And knowing Chuck -- he was definitely not one to let things lie.

Poor Lily van der Woodsen. Bart Bass had promised her that she was the only woman in his life. No more 25 year-old leggy models. His eyes were on her, and her alone. So Lily was in for a big surprise when she found a drunk Chuck stumbling outside the Palace Hotel. He had a drink (or five) to ease his pain over what happened between him and his father. While Lily helped Chuck up from the ground, he went off on how his dad told him he wasn't committed to anything. But who was his dad to tell him he wasn't committed when Bart was being unfaithful to Lily? Lily assured Chuck his father was being loyal to her. Chuck told her if Bart was supposed to be so loyal to her then what was he doing with some Asian girl today? Oops. Lily's face turned white as she quickly excused herself and ran off.

At least someone in the van der Woodsen family was having luck in the love department. Lily's daughter, Serena, was having a wonderful time with her current beau, Dan Humphrey. Lonely Boy was definitely not lonely anymore (we're gonna need to come up with a new nickname for him). Dan and Serena were caught making out all over school grounds. Word even got out there was live stream of them doing 'it' on my site (but that was totally just a rumor. Gossip Girl is a sex tape free zone). Even when Dan and Serena were in the privacy of Dan's own home, they had a pesky peeper. Seemed Vanessa, Dan's long lost friend, did not know how to knock. She suddenly appeared every time the couple was about to get down and dirty. But maybe that was a good thing. Like we've said before, Dan Humphrey had barely even talked to a girl before Serena van der Woodsen came along, let alone done anything with one that involved any kind of bodily interaction. Dan was having some issues. Since he had absolutely no experience whatsoever, he was nervous. Thank god for the Internet. After some intense Googling, Dan finally got some insight in how to be a love machine. And with his dad putting in a 24-hour projection installation in his art gallery, Dan was going to have the loft all to himself; the perfect time to have some real alone time with SVDW. OMFG! Okay, we know she's not a virgin and all but still. Serena was gonna have sex! With Lonely Boy! In Brooklyn! This was huuuge!

Meanwhile, Dan's little sister, Jenny, was doomed. A jeweler had lent her a diamond bracelet for the masked ball and somehow she managed to lose it. The bracelet was worth more than Jenny's apartment. If she didn't find it, she'd be picking up trash on the West Side Highway. Jenny also had Nate Archibald to worry about. He confronted her in the school hallway about what happened at the masked ball. Nate tried to bribe Jenny with chocolate (come on N, you can do better than that) so she wouldn't tell Blair he had kissed her thinking she was Serena. Blair interrupted their conversation and Nate quickly gave her the chocolate as an apology for not being so appreciative of her. Blah blah blah. As Jenny backed away from the Blair/Nate moment, Blair ran after her and held up the diamond bracelet Jenny had lost. Busted. Blair knew Jenny was at the ball. Blair told her friends don't lie to each other nor do they keep secrets. And Blair and Jenny are friends. Blair helped pay for the broken clasp. But this was the last time she would ever help Jenny out. Game recognizes game. If Jenny ever crossed Blair again, it'd be over. Jenny promised her it would never happen ever again. Blair was relieved. She didn't want to have a Constance Billard Freshmen Revolution on her hands. Then, Blair broke some big and exciting news to Jenny. Turns out, Nate's mom told Blair's mom that Nate was going to give her his family ring! This was a ginormous deal. Sure, they wouldn't get married anytime soon but it was a token of Nate's commitment to her. Jenny looked upset as Blair was rejoicing. Blair asked her why she wasn't happy for her. That's when Jenny broke even bigger, but not so exciting, news to Blair. She told her all about what happened with Nate at the masked ball. Blair was heartbroken as she demanded Jenny to leave. What a buzzkill, J.

You gotta feel kind of bad for Nate. He was having major issues with the fam. With Lindsay Lohan just released from rehab, there was an extra spot for Nate at the Cirque Lodge. And that's exactly where Nate's mom, Anne, wanted to send him. After finding cocaine in their apartment, Anne was certain it was Nate's and was going to stop at nothing to get her son the proper treatment. The cocaine was actually his dad, the Captain's. When Nate confronted his dad about this, The Captain assured Nate he would talk Anne out of sending him off to Utah. The Captain was just having a rough time at work. Someone gave it to him to ease his troubles. He's not a drug user and will flush the bag down the toilet ASAP. Unfortunately for the Captain, Nate was still weary. Nate followed his father and caught him buying more coke. The kids on the Upper East Side aren't the only liars on the block. Their parents are guilty of that too. Big time. The Archibalds went over to dinner at the Waldorfs to celebrate Nate's dad taking Eleanor's company public. When Blair saw Nate she was ice cold to him. She asked him if there was anything he wanted to tell her and Nate said no. Blair rolled her eyes and had to pretend to enjoy spending time with Nate and his family. Nate's dad acted really weird and wired the whole night. He even went as far as to pester Blair into trying on the family ring. Nate sensed the uneasy tension and suggested to his father they go outside to smoke some cigars. When they got outside, Nate confronted the Captain. The Captain was obviously tweaked and that's why he was acting all crazy. The Captain didn't want to hear any of it. He's the adult, Nate's the kid. While Nate tried to stop his father from going back inside, the Captain punched him. As luck would have it, a cop car was just passing by and saw it all. They approached the father and son to see what was going on. Nate apologized to his dad as he told the cops to check the Captain's pockets. Sure enough, there was a bag of cocaine. The police arrested him and took him off. The Captain better have a good lawyer. Blair saw the whole altercation from her bedroom window. She went downstairs and confronted Nate. Blair told him about how upset she was that he didn't even try to find her at the masked ball. While she was waiting for Nate to get to her so they could finally be together, he was off confessing his feelings for Serena. Blair's had this grand idea about their future together ever since she was a little girl. Maybe she's been wrong this whole time. As Blair got into the limo alone, she told Nate he should go and be with his family. Next stop for Blair: Victrola. Next stop for Nate: who the hell knows.

As Chuck continued to sulk at Victrola, his father, Bart, returned to the club; along with the sexy, young Asian woman from the other day. Bart introduced her to Chuck. Her name was Pauletta Cho and she had recently written an article about Bart in the New York Observer. Pauletta was looking for a change in career. Instead of writing about titans, she wanted to become one. And her first order of business? Checking to see if Chuck's venture was worth Bart's investment. So I guess Bart Bass wasn't shagging her. Oops...Chuck admitted to his dad what he told Lily. Bart was disappointed but knew he couldn't really blame Chuck. Guess Bart has taught Chuck more than just how to spot a good investment when you see one.

With his dad and Jenny out of the loft, Dan transformed his bedroom into a love shack, complete with candles (a total fire hazard) and a special devirginizing mix tape (how Lloyd Dobler of him). The scene was set and now the only thing left to do was 'it'. As they were getting down to business, Dan was trying out all the moves he'd learned online. Then suddenly, Serena stopped him. She was scared. Not of Dan but of the whole situation. No guy had ever looked at her the way Dan did. Maybe it was better just to take it a little slower. They both really liked each other so there was no rush to have sex right away. Dan and Serena will wait until they are both ready. Aw, so romantic. Doesn't it make you want to just puke? But in a good way, of course! While Dan and Serena were not doing it, Jenny was seen on the Metro North heading upstate. We hear she was paying a visit to her mother up in Hudson asking her to come home. This should be interesting now that Jenny's dad, Rufus, and Serena's mom, Lily, have been hanging out so much. And what about Lily and Chuck's dad, Bart? Is she going to take his word that Pauletta was just an apprentice? Or was this the straw that broke the camel's back? Oh, a tangled web we weave...

Once Blair arrived at Victrola, she told Chuck she thought Nate and her just broke up. Chuck was aghast. Blair and Nate? Broken up? Blair needed a drink. As the two watched the burlesque dancers perform, Blair told Chuck she had moves too. Chuck doubted that. Blair raised an eyebrow and told him to guard her drink. She got on the stage and unzipped her dress. Can I get another OMFG? This was soooo not the Blair Waldorf we all knew. Blair slithered out of her dress and did her sexiest moves in just a slip. Showgirls this was not. But rather, Upper East Side Socialite Lets Down Her Guard. At the end of the night in the limo, a tipsy Chuck told a tipsy Blair she looked amazing up on stage. And it was exactly what Blair wanted to hear. The two started kissing and one thing led to another and...well, let's just say our favorite virgin Queen is no longer a virgin. Yes, she and Chuck did it. And she hadn't even been broken up with Nate for more than a few hours. You just can't keep a bad girl down.

What is Nate gonna say when he finds out his best friend had sex with his girlfriend? Oh wait, his EX girlfriend. Maybe Nate will get a dose of his own medicine? Or maybe he just won't care? We're thinking the latter. Things went from bad to worse for Nate and his family. Nate's father's bail was set at a million dollars. Cocaine possession wasn't his only charge. Turns out the DA had been working on a case against him for some time now, on allegations of embezzlement and fraud. Orange is so not the Captain's color.

So with Dan and Serena hooking up, Blair and Nate breaking up, Bart and Lily doing a little bit of both, this has been a pretty crazy few days. But our favorite pairing of the week has to be Blair and Chuck. Is the UES really ready for a Blair/Chuck relationship? I'm not sure the UES would be able to survive. What happens when Medusa has sex with the devil? Surely, souls will be sacrificed. We say, "Go Blair!" Girl has been repressed for too long and we're glad Chuck finally broke her out of her shell. And you what they say: the best way to get over someone is to get under someone else...

xoxo GOSSIP GIRL

November 6, 2007