Gossip Girl's Nate and Blair were quite the iconic couple for the first two seasons of the show. Unfortunately for these two characters, their relationship was mostly filled with drama and heartache. Nate and Blair had been together for years and Blair was convinced that there would be wedding bells.
Of course, Nate had other plans in mind. The series' pilot revealed that Nate and Blair's best friend had previously gotten together and Blair had no idea that her world was about to be turned upside down. When this information came to light, Blair started to spiral. This was the beginning of the end for Blair and Nate's relationship but it wouldn't be Gossip Girl if there wasn't plenty of drama first.
Nate Did To Blair: Got Together With Serena
If there's one thing that caused most of the drama between Blair and Nate, it's the fact that Nate got together with Serena. Not only did Nate cheat on Blair, but he cheated on Blair with her best friend. It doesn't get much worse than that. Oh, except for the fact that Nate didn't come clean about any of it until a year later.
All of this created plenty of mistrust within Nate and Blair's relationship. Naturally, Blair felt completely betrayed by Nate and started to spiral out of control.
Blair Did To Nate: Tried To Force Him To Say "I Love You"
Prior to Blair finding out about Nate and Serena getting together, Blair had an inkling that her boyfriend had feelings for her best friend. She went to great lengths to ignore the signs, including telling Nate that she loved him, hoping he would say it back. In her mind, this would suddenly make her and Nate's relationship solid and untouchable by anyone, including Serena.
Right as Serena came back to town, Blair did everything she could to hear those words from Nate but it just seemed forced and slightly manipulative.
Nate Did To Blair: Kissed Jenny
Nate took his feelings for Serena way too far when he kissed Jenny at the masquerade ball in season one. Jenny was wearing Serena's mask so naturally, he thought she was Serena. He then continued to confess his love for her and ultimately kissed her.
When Nate found out it was actually Jenny who he kissed at the ball, he bribed her with a box of chocolates to keep it a secret. This all makes Nate look pretty bad. He had several opportunities to come clean to Blair but he continued to lie and cheat.
Blair Did To Nate: Got Together With Chuck
Nate was rarely one to come clean to Blair about his actions but Blair had her sources. She managed to find out from Jenny that Nate kissed her (thinking she was Serena) at the masquerade ball. This was the final straw for Blair as she had put up with Nate's cheating before and he had broken her trust once again.
This definitely caused Blair to spiral and she looked to Chuck for comfort. Unfortunately, Chuck was Nate's best friend, so this came off as a pretty vengeful move on her part.
Nate Did To Blair: Dated Blair When He Had Feelings For Serena
Nate dated Blair for a long time, regardless of his feelings for Serena, which was a pretty slimy thing to do. Not only did Nate stay with Blair after he had gotten together with Serena, but he also stayed with her when Serena came back to town, knowing full well that his feelings for his girlfriend's best friend were still lingering. Even worse, Nate went out of his way to secretly meet with Serena, all while Blair was in the dark about her boyfriend's cheating and true feelings.
It was extremely manipulative of Nate to keep Blair on the hook this entire time and withhold information that she deserved to know.
Blair Did To Nate: Convinced Him To Break Up With Vanessa
When Nate and Blair got back together for the third and final time, Nate was technically still dating Vanessa. Blair convinced Nate to break up with Vanessa so that they could be together. Of course, it didn't take much convincing. Nate told Blair that he felt things had "come to a natural end" with Vanessa and he was sure Vanessa thought so too.
Of course, Vanessa didn't feel this way at all and was pretty upset when Nate broke up with her. Vanessa was easily able to see through Nate's breakup speech and knew that he was leaving her for Blair.
Nate Did To Blair: Almost Gave Blair His Family Ring
When Nate's family learned that he had finally pulled the plug on his relationship with Blair, they weren't too happy. Nate's family was linked to Blair's family business-wise, so it was important that they stayed in the Waldorfs' good graces. Nate's mom momentarily convinced Nate to get back together with Blair and give her their family ring just to keep the Waldorfs from being upset with them.
Luckily, Nate came around and didn't go through with it. However, the fact that he even considered toying with Blair's feelings in this way says a lot.
Blair Did To Nate: Agreed To Convince Nate To Attend Yale
During Blair and Nate's third go at their relationship, Nate's grandfather struck a deal with Blair. He promised to help her get into Yale if she worked to persuade Nate to attend Yale as well. Of course, Blair knew this wasn't necessarily what Nate wanted but she convinced herself it was the right thing to do for both her and Nate.
Unfortunately, Nate's grandfather ended up outing his and Blair's deal to Nate which inevitably made Blair look bad. Nate was angry at first but he eventually forgave her for conspiring with William.
Nate Did To Blair: Bought An Apartment To Keep Blair Away From Chuck
In season two, Nate started to sense that his girlfriend and his best friend had some real feelings for each other. After all, the two were spending plenty of time together and constantly planning new schemes. It was obvious that Blair and Chuck had a bond that Nate wasn't a part of, they bonded over their love for mischief and Nate just couldn't relate.
In an effort to keep Blair and Chuck apart, Nate bought an apartment for him and Blair to live in together. Unfortunately, this plan didn't pan out as Blair and Nate broke up shortly after.
Blair Did To Nate: Chose Chuck Over Nate
No surprise here but Blair ended up ditching Nate on what was supposed to be their first night together in their new apartment. In "Southern Gentlemen Prefer Blondes", Blair left Nate to go conspire with Chuck and track down Georgina Sparks. Of course, Nate was extremely hurt that Blair chose Chuck over him.
Nate had specifically gotten this apartment in hopes that it would bring them closer. Unfortunately, it drove Blair even further away. She didn't admit it at the time, but this was just the beginning of Blair choosing Chuck time and time again.