He wanted to take her out on an amazing date. The kind of date you never forget, the kind of date you tell about to all your friends when trying to make them jealous. The kind of date you write about in your diary, the kind of date you compare all your other dates to, just to realize that this one is the most amazing you've ever been on.
Really, he just wanted her to have a good time. He had thought about doing something classy and elegant, like hiring a limo to drive them to one of those overpriced restaurants where they would have eaten frog legs or any other disgusting but sophisticated dish. But then he remembered his first date with Serena, four years ago, how awkward it had been at first and how she had enjoyed the " real " date, so he decided to take Blair on a " real Dan Humphrey date " - after all, it is what she had asked for.
He knew Blair wasn't Serena. He knew every guy she had dated was either and Upper East Sider, a fucking Prince, a Lord, or an Ivy League student. He knew she was used to be treated like a princess, he knew she was always expecting too much from everybody. But despite all that, she had agreed to a date with him. So why pretend to be someone he wasn't ?
It didn't take him long to figure out where he was going to take her.
The two days seemed to last forever, but finally, Friday night arrived. He put on a pair of jeans and a shirt before leaving the loft to go pick her up.
For the first time of her life, Serena wasn't over at Blair's to help her get ready for her date. Usually, she would arrive at 3 o'clock, they'd make some pop corn and watch and Audrey Hepburn movie. Then they would spend hours going through all of Blair's closet before finding the perfect dress. Serena would do her hair and her make-up, tell her how beautiful she looked, and then the guy - whoever he was - would arrive, and Serena would wait for Blair to come back home and tell her how wonderful her evening was. But this time, Serena wasn't here, simply because Serena had no idea she was going on a date with Dan. Blair knew that, deep down, Serena still had feelings for Dan - she would always have - and wasn't sure how she would react if she knew about this date.
So she was all alone to get ready, and she found it extremely hard to find something appropriate to wear. I mean, she had no idea where he was even taking her, which made the task even more difficult. Was she supposed to wear heels or flats ? A dress or jeans ? Something elegant or casual ? As if Blair Waldorf ever wore anything casual.
As if Dan Humphrey would take her somewhere elegant.
She ended up choosing black skinny pants with a form-fitting top. She had tried to be as casual as possible, but heels were essential. While doing her makeup, she thought about how weird things had turned out. She had known Dan for about four years and had always despised him. When Serena first started dating him, she couldn't believe her eyes. And now, she was going out on a date with him. And she was actually nervous about it.
About ten minutes later, she heard the elevator doors open. She rushed downstairs, not wanting Dorota to greet him and start asking embarrassing questions, like what he was doing here. She hadn't told her about their date - she hadn't told anyone really - and prefered to keep it this way until she knew for sure this was serious. Then, she would worry about telling people. But as for know, she just wanted to have fun, and enjoy the evening.
