Disclaimer: I don't own Gossip Girl.

Author's Note: So I was a huge fan of Bart and Lily and I seriously think they should have put more effort into that, instead of persistently playing up the whole "poor little rich girl Lily" thing; they already had that covered with Serena. So yes, I think a little more focus on Bart, showing his human side and showing why Lily and Bart fell for each other is what I wanted and this is the product, along with weekly drabbles.

Fairytales in New York

The first time she sees him, really sees him (beyond the facade that's accepted in their society), isn't in the least the first time she meets him. She's met Bart for years, at the occasional school function, more rarely at the formal appropriate parties. Most of the time, she's met him at those risky parties her mother disdains so much and that she finds herself flirting with.

Not that they do any flirting. Not really anyway. There's a few glances shared and she sort of assumes that he finds her attractive. There aren't many men that don't find Lillian van der Woodsen attractive. What does surprise her is when she starts finding him attractive. That doesn't happen the first time she sees him either; then, she just feels a tug of sympathy within her heart when she notices the momentary look of grief on his face when his wife is mentioned in passing.

Who knew Bart Bass had such a sentimental heart?

The next time she had met him – not really seen him – she thought she must have imagined the whole thing. He had a bimbo on his arms, the kind that looked like she knew ways to have sex that Lily couldn't even imagine. Not that Lily could judge herself; having just gone through (another) divorce a mere two weeks ago, she was already presenting her latest boyfriend to Polite Society.

Who turned out to be as dumb as a brain-damaged illiterate child, when Bart entered the conversation.

And she had to admit...it was kind of fun talking to a guy who seemed as dismissive and acerbic about the blatant falsities in their world as she was herself, whilst doing so with a polite, dismissive smile on his face and a few (oh so subtle) jabs at their peers. And he made her laugh. And more than making her laugh, he had looked at her in that way.

In that way that made a blush creep to her cheeks and seemed to suddenly fluster her, though goodness knew why!

They met a few more times after that, though Lily couldn't have said when or where or why. She was far too distracted by a daughter that seemed hell-bent on ruining her life and maybe ending it long before it was due, and she suspected that Bart was kept busy with his own son, essentially a male version of Serena.

She was a little too busy with her daughter to notice her son slipping away.

But it didn't matter; she saw him a few times, they exchanged a few pleasantries. Lily had long since dumped that first idiot after her last divorce; her latest boyfriend was far more presentable, far richer and so torturously dull. But at least he could hold a conversation with Bart! She wasn't sure how but somewhere down the line, she began to hold her standards against Bart. At least intellectually speaking. Bart wasn't really that much of a looker (though when he looked at her like that, it still had her heart thumping violently against her chest) and for all the women he had on his arms, she hadn't yet seen anything of his alleged charms. But regardless, when she now met prospective suitors, she found herself assessing them to see if they could hold their own against Bart – in a conversation. She had little doubt that they could do it in business. There was a reason Bart's name was infamous in business circles and even with her own meagre knowledge, she knew she would never go against Bart's advice in that area.

Maybe not in the sexual area either; goodness knew he was experienced and she couldn't quite imagine all that he could do...

She pushes such thoughts away, breaks up with the boring guy, dates a couple of others (for a couple of dates only), and finally finds a guy who's charming, rich and funny. Sure, he doesn't look at her the way Bart did once in a while, from across the room. And sure, he's point of view is a lot more optimistic and naive than hers. But who wants to be with an embittered man, even if he makes her want to laugh so hard, she once choked on the cocktail she was drinking. She's happy with him and she often meets Bart at various functions, a different bimbo each time. And she isn't judging them (too much). She's just critical of everything they wear and everything they say and everything they do. Because shouldn't Bart, with his dry humour and cutting comments, get bored with these nitwits?

Even though she knows as well as anyone that people don't necessarily look for equals when they're in it for the sex.

Regardless, she's enjoying this man, even if she disparages half of the things he says, is embarrassed of the other half, ignores all of his opinions and generally avoids eye contact with one Bart Bass if he happens to be in the room. And she thinks he's really into her – gives her flowers, flowery compliments too and he's more than willing to be amorous with her. Which is why it's a complete shock (less disappointment and more the humiliation) when he breaks up with her in full view of everyone, spoken at full (and drunken) volume. Bart's in the room and she's assiduously avoiding his eye. She's trying, and probably failing, at keeping a very embarrassed flush from raiding her cheeks but tears are nowhere in sight. He was nice and everything but her heart just wasn't in it, not really. But it's more than a little humiliating and she doesn't think it fits her ladylike status if she slapped him in the face or kneed him in the balls like she so desperately wants to do. Instead, she grabs two cocktails, downs them both and grabs a third. She can't avoid Bart completely, which is how she sees him, from the corners of her eyes, propelling the drunken bastard out of the room. She's never sure what happens or who does what (though she has very strong suspicions that it's all Bart Bass) but the next thing she knows is that the guy has lost his job and left New York for humbler surroundings. Honestly speaking, she's ok with Bart doing this on her behalf (assuming he did it and assuming it was for her).

She'll never understand why she likes his mysterious, underhanded ways, done on her behalf, when she despises her mother for doing similar things. She doesn't understand why this flatters her, how she's ok with him doing things on her behalf without her permission or knowledge...

And then her world crashed around her. She found her baby boy, the most wonderful, innocent, selfless person in her life, bleeding away. And she didn't know what to do!

What the hell could she do?

Her fingers itched over numbers on her phone – who to call, what to say, what to do... Serena was a must but it was too unpleasant to do. She should probably call Cece but she was too ashamed. She could call Bart, have him sort things out in his own effective way, remove all the stress and worry about what to do and leave her with just pure concern for her son. But she shirked from that, couldn't stand losing face in front of him. So in the end, all she did was put him in a home, known for its ability to keep the secrets of their residents, the kind she'd been in.

She wouldn't think back to that time; she refused to. Those giddy days and dizzying nights with Rufus, flaunting all of her misdemeanours in her mother's face, rebelling in the only ways known to her...

A wonderful time but so stupid, when she looks back on it. She's a mother now, with a family to protect, a face to show. So she dropped Eric off at the home, stayed with him for a few hours, went home to get ready and went to the party she was supposed to that night. And she had a tight, artificial smile on her face the whole time. After all, she couldn't let her baby be ogled at and if that meant facing these heartless members of her society with her fake smile firmly in place, so be it.

Of course, by the end of the party, the pain in her cheeks from her strained smile and the headache from listening to all the bullshit, worrying incessantly about what her son might be feeling and what her reckless daughter might be doing left her with the strongest urge to cry.

Which was when she finally saw the infamous Bass charm...

Awkwardly clearing his throat and carefully looking away from her, he started mumbling about how he doesn't know how to do this with her type of women-

Her type of women? What exactly did he mean by that?

He went on to explain that normally he kissed women who were paid for it or women who were good for nothing else. To find a woman who's interesting to talk to, has class, a neurotic and intimidating personality and sex appeal that could be more destructive than nuclear warfare, how does one go about kissing a woman like that?

There was a certain amount of charm, seeing a grown man flounder and stutter like a teenager; especially a man of Bass' reputation.

So she showed him how it was done. You act like an insecure teenager, flatter the woman liberally, comforting her in her time of need without realising it. And then, you get her to kiss you.

And really, it wasn't a whirlwind romance or an epic tragedy. There was nothing Romeo-and-Juliet about them. But it was Bart-and-Lily, quiet, behind the shadows, surreptitiously taking place until Lily and Bart became Lily-and-Bart and she kinda liked it. He liked it. And it sort of worked, in a sort of dysfunctional way that she couldn't understand, no matter how long or hard she thought about it. They sort of worked.