Author's Note: I have wanted to write a "what if Blair really was pregnant in season one?" story for a while now. My attempt morphed into this AU thing that has been written, deleted, rewritten, and recused from my computer's recycling bin multiple times. It uses scenes from the show, which makes me rather nervous given what happened the last time I tried this in a different fandom. Anyways, the key point is that this is an AU fic that borrows scenes from the show.

The title of this piece comes from Laila Lalami's novel, Hope and Other Dangerous Pursuits. At some point whilst writing this my eye happened to land on the spine of the novel and I could no longer shake the idea that this story has to be called "And Other Dangerous Pursuits". It, of course, breaks my implicit rule that all fics have single word titles, but sometimes things fit too well.

Nathaniel is running late. Or, so Chuck deduces from the passing time and the lack of text or call on the part of his best friend. This kind of behavior – showing up late, not updating people on his whereabouts – would never fly with his father, but then again Nate's parents actually love him and this is not a business meeting.

The bar is crowded; the hostess looks overwhelmed. His finger has been off the pulse of the Manhattan social scene for long enough that he has never even heard of this place before. But the amount of people crammed into this establishment, the amount of people trying to beg for a table makes it plain that this is the place to see and be seen. The scotch isn't bad, and the wait is nothing a hundred dollar bill or two can't solve. People like him don't make reservations and, even if he had, Nate's tardiness would have made them already miss it.

Instead, he orders another scotch and scans the room, appraising the appearance of every woman in this place. He doesn't look twice; he never looks twice at the same woman. Yet, when his eyes settle on the brunette at the end of the bar, he finds that he cannot look away.

He watches the way her finger skims the rim of her half-drunk martini glass. He watches the way her curls fall in front of her face, the way they bounce and sway every time the door to this establishment opens and the gust of wind catches her in its breeze. He watches the way her hips shift and her knee-length silk dress rides up every time she crosses and uncross her legs, the way she ignores every man who approaches her.

Suddenly, it becomes a challenge, a game. He wants to saddle up next to her, take her down a notch and gain her attention. But, most of all, he wants to know why she looks so damn bored.

"You look ravishing."

She looks directly at him, and he is taken aback by just how beautiful she is. The look on her face is one of surprise; he can tell the comment, the heat in his voice has startled her. But just as quickly it is replaced by disgust as her eyes roam over him, mentally picking him apart like a buzzard picks apart a carcass.

"Is that your pick up line?"

Her voice is dripping with incredulity, and he rewards her with a smirk. He's never used those words on anyone before so he is unsure of the follow-up. Now it seems silly to have expected her to just fall into his arms, to just demand that he take her now.

"I'm engaged," she informs him, thrusting the diamond on her fourth finger in his face. She sounds smug and the diamond looks oddly familiar, but he doesn't care because engaged is not the same thing as married.

"Where's your fiancé?"

The smug look on her face falters for a brief moment. She starts to explain how he is running late but cuts herself off and states that her fiancé's whereabouts are none of his business. Her attempt at an explanation is useless, though. He is far too enraptured with the shape of her ruby red lips to listen.

"If I was your man," he informs her as he drops his voice and leans closer to her ear. "I wouldn't need instructions on how to find you."

He backs away with a self-satisfied smirk. She is too good at this to give him the satisfaction of a shiver, but he can see the gleam in her eye as she opens her mouth.

"Or ravish me, I'm sure."

He is stunned, frozen in his spot over her reply and unable to do anything as her smirk morphs into a picture perfect smile and she slides off her stool. For a brief moment, he thinks she might actually be taking him up on his implicit offer and thus be easier than he thought. But she slips past him, greets the man who has stopped next to him with a kiss.

"Sorry I'm late," the familiar voice apologizes. "Oh, good, I see you've met Chuck."

The contribution of his name makes everything click, and he turns to his left to see the brunette tucked into the embrace of his best friend. Nate conducts formal introductions as the smile on her face disappears for a moment. Chuck offers his hand, jumps at the electricity that courses through him as her slim fingers slip into his palm for a handshake.

And then he knows he's fucked because the woman he has taken to calling the Ice Queen, the woman with the witty retort is his best friend's fiancée.

He barely manages to make it through dinner, focuses the conversation entirely upon his latest business venture and makes a point of ignoring her. She seems disgusted to learn that he is trying to purchase a burlesque club, grows increasingly annoyed with his rude behavior. He comes up with an excuse that sounds lame to him (and her), but Nate buys it and he is able to escape before dessert. And, as Arthur speeds through midtown Manhattan, he makes a promise to avoid her at all costs.

Except, on Tuesday, Nate calls him and rambles on for fifteen minutes about some emergency at his father's company that he needs to help handle before asking him if he can please take the time out of his day today to drive up to New Haven. He asks why before he remembers that the Ice Queen lives there, that the Ice Queen is a freshman at Yale.

He tries to come up with an excuse to get him out of whatever Nate wants as he listens to Nate explain that Blair is giving a speech representing the freshman class that is really, really important to her. His best friend sounds almost desperate as he confesses that he completely forgot until her reminder text this morning, and he feels irrationally angry over the fact that he remembered even though she mentioned it only once at dinner last week.

But Nate's got him by the balls, reminds him of that time that he covered for him to Bart and prevented him from getting shipped off to outer Siberia. (Boarding school in Switzerland was bad enough, and Prague at least possessed some semblance of civilization.) The photographic proof sent to his phone is more than enough incentive. He just got back into his father's good graces, just got invited back to New York, and he's not about to be banished again.

So he instructs Arthur to drive him to New Haven, tries to formulate a plan for dealing with brunette curls and ruby red lips as he edits his business plan during the nearly two hours it takes him to get from the Upper East Side to the Yale campus. Nate's directions are shit and it takes eight coeds – coeds he'd rather be following back to their dorm rooms – to find the right building.

He barely manages to slip into a seat in the back before the program begins, but he doesn't go entirely unnoticed. By the time he is settled into his seat, by the time he spies her on the stage, her expression has morphed from masked anxiety to masked confusion. He offers her a shrug but the lights are already dimmed and his movements go unseen.

The program is long, longer than Nate had estimated, and it's over an hour before she is announced. She moves gracefully, commands the podium as though she is queen and the audience is full of her subjects. Maybe not always loyal, maybe not always deferential, but her subjects none the less. Her speech is poised and perfect just like her, but he does not miss the not-so-subtle digs at her competition even if everyone else does.

He waits near the back row of the auditorium, watches as everyone from coeds to professors flock around her and watches as her expression changes to an odd combination of disbelief and disgust when they are the only two left in the auditorium. The flowers are thrust into her hands as she asks him what he's doing here, as she eyes the red roses with distrust.

"They're from Nate," he informs her. The statement isn't entirely true. Nate didn't even mention bringing her flowers, but he figures that's what boyfriends do and girls like red roses, right?

"He, uh, couldn't make it. He sent me instead."

"You're not going to take me out to dinner, are you?"

Her question throws him for a moment. Nate said nothing about dinner; he was only supposed to show up and hear her speech. But the way she asks it makes it sound like she is expecting him to do so, to want to do so.

"Do you want me to?"

"You're not my boyfriend," she reminds him, although he's not sure if the reminder is for him or for her.

"I have a lot of homework, anyways," she demurely adds. It's the perfect excuse, but neither of them grasps onto it the way they should. Instead, they stand in an empty auditorium and try to figure out how to extradite themselves from this situation.

"Here I thought you were the perfect Upper East Side princess."

"Excuse me?" She cries out incredulously.

"You could at least play the proper hostess and offer to show me around," he replies. "I drove all the way up here, and you're just going to send me off without giving me a tour. I've never been on a college campus."

"I find that hard to believe," she retorts. He smirks at her response, amends his early statement to state that he's never been on the Yale campus before.

"Why do you care?" She asks just as he asks himself the same question.

Because the truth is that he doesn't care, but the way she talked about Yale in her speech makes it sound like the most exciting place to be. More exciting than a brothel in Prague, more exciting than his new club on a Friday night. Except her eyes don't match her mouth, and he wants to know why that is.

"I don't," he snaps. "I just want to know where to find the easiest coeds. I figured who better to ask than an insider."

"You're disgusting," she announces before turning on her heels and stomping away from him.

He doesn't bother calling after her, doesn't bother following her. Rather, he watches curiously as she drops the dozen red roses in the nearest trash can before fleeing the building.

The following Monday Nate invites him out to dinner. He accepts because he thinks it will be just the two of them, but he arrives at the same restaurant he first met her in to see her seated next to his best friend. Across from them is a blonde woman, and it doesn't take a genius to figure out that this is a blind, double date.

Nate mumbles an apology to him when they greet each other, and his perfunctory greeting to his best friend's fiancée is met with her own introductions. The woman seated with them really needs no introduction because even he has heard of wild child Serena van der Woodsen despite not living here for the last three years.

Serena's better qualities are praised by the couple across the table from him with Blair gushing and Nate nodding his head in agreement. She's a freshman at Brown just visiting for the weekend but she grew up on the Upper East Side, and, Chuck, did you know that Serena and Blair have been best friends since they were four?

Truth be told, Serena is blonde and beautiful and has breasts and probably would have been his type. But tonight he is far more fascinated by the way Nate's eyes are following his fiancée's best friend (and maid of honor, he is informed during the course of the dinner) rather than his fiancée and by the way Blair's eyes aren't matching her mouth as she tries to encourage something between him and Serena.