A/N: So after the "let's-pull-storylines-out-of-a-hat-finale" I didn't want to even think about the sheer stupidity that is Gossip Girl ever again. But then I thought of this, and idk, here we are? Chair Marriage/Baby, but no Dan is GG or Derena marriage bullshit. And yes, Dair are married in this. Confused? So am I?

A/N 2: I don't know why, but I always pictured Chuck's son as the opposite of his father. A decent guy who treats women right. False hope? Whatever. Fuck you all. But enjoy.

Henry Bass' life had never been full of certainties, to say the least. Even when you're spoilt, rich, and the guy who has managed to sleep with half the girls in his years (he can practically hear Emily's remark about that), your life isn't perfect. Or certain. Sometimes your mother marries a guy who isn't your father. Sometimes your father marries a French ex-prostitute. Sometimes your parents get divorced for the previous two to happen. Sometimes you have to pay five thousand dollars to allow your teacher to let you pass Senior English. Sometimes you lie to your mother about that. Sometimes you meet a girl in college that you really like. Sometimes you don't know how to deal with that.

But, there were certainties in his life. He could get hammered one night and by midday the next day, be completely free of any hangovers becausegodblessthebasshangov ercure. He could score any girl just by saying his last name. He could always count on his little sixteen year old half sister ("Sixteen, eh, Em? I lost my virginity at sixteen." "I think we both know that's a lie, Mr I Sleep With Girls At Eighth Grade Camp And Never Talk To Them Again So I Become a Cautionary Tale Across The School.") to be sitting on her bed, cross legged, with a book in her lap on Thursday afternoons.

This Thursday afternoon is no different.

"Emily, Emily, Emily. We need to talk."

"Don't you have school?"

"What are you, our mother?"

"No, but I've been told we're very similar."

"Too similar. You're not going to bite my head off, are you?"

"Depends. Did you have sex with a girl and refuse to call her? Did you and Michael go to Atlantic City and forget all about it again? Did you screw my best friend?"

"I never did the last one."

"That's because one of them is a lesbian and the other, being the female equivalent of you, knows exactly how to avoid sleeping with you."

"I'm charmed."

"Should be. Anyway, what's up, jackass?"

"Obscene language for no reason. I'm offended."

"You're only offended because I'm one of the few people who tells it like it is."

"I can be nice."

"Can is the keyword here."

"Haha. But, I do have to talk to you."

"So talk."

"You sound stressed."

"I'm busy tonight."

"Oooh, hot date?"

"No, I'm planning to kill my half brother. Talk."

"Touchy touchy. But, look. You're the Queen of Romance-don't give me that look-and I need help."

"Going up to girls and saying 'Hey, I'm Henry Bass' not working anymore?"

"Oh no, it's working. But it's something different. There's this girl. And, she's, well, she's great. And I don't know what to do because-"

"Shit."

"What?"

"My sadistic older brother has a crush."

"Half brother."

"Not the important thing here, Henry."

"Whatever. It's not a crush."

"Fine. Love."

"It's not love! I just want to get past the fucking part, okay?"

"For you that's like a marriage proposal."

"Don't start."

"Right. Sorry. So tell me about this girl."

"Her name's Victorie. And she's blonde and from Monaco and I'm pretty sure she's royalty, but she doesn't talk about her family, so I can neither confirm nor deny it."

"Like father, like son."

"Shut up."

"Mmmm, you're real good with people who you require assistance from, aren't you?"

"Just tell me what to do."

"Be yourself."

"I was expecting something a little less cliché."

"I was expecting something entirely different too, so, we're on the same page."

"But really? Be myself? Come on, E."

"Henry, you're a jackass. I know this. But you're also a sweet guy. If this Victorie girl really means something to you, be good to her. And let that Henry Bass shine. That's all I can say."

"Sure it'll work?"

"Nope."

"Thanks."

"Do you have a better idea?"

"No."

"That's exactly what I thought."

Henry Bass did have certainties in his life. And one of them was that his little, half-sister, Emily Serena Humphrey, had twice the brains he did. And knew romance better than Henry knew the back of his hand.

It figures, with parents like hers.

A/N: Shit son, I don't even know.

A/N 2: Michael, is, for those wondering, Scarter's son. Emily's lesbian best friend is Nate and Jenny's daughter, and her other best friend is Michael's twin sister. They were all characters I invented when writing Gossip Girl: Second Generation, which has now be scraped.

A/N 3: In GG:SG, Emily was to end up with Hugo, Cheva's son. Their OTP name was going to be 'You owe me a dance.'

A/N 4: Yeah, it would've been fucking brilliant.

A/N 5: Happy Holidays!