Disclaimer: I do not own any of the characters from the Mortal Instruments or the Infernal Devices. They belong entirely to Cassie Clare (who is, in my firm opinion, a literary goddess). I do own Beatrice and the younger Max, however (though I suppose you can use them if you ask me very nicely). This story takes place when Clary and Co. are in their forties and have teenaged children of their own.

XxX

"Kid," the bouncer said grumpily, "I don't care if it's part of your Halloween costume. You can't bring that thing in here. Either chuck it or get out of line." The boy, stick-skinny with slanted Asian eyes, muttered something under his breath before handing the small sword- plastic, but well-made and pointy enough to cause a fair bit of damage- to the bouncer before shuffling into the club. It was easy enough for Simon, with his vampiric grace, to sneak in behind him, unseen by the bouncer and the long line of teenagers eagerly waiting for entrance.

The Pandemonium Club, like Simon, had changed very little over the past twenty-odd years.

Simon scanned the crowd for the telltale splash of golden hair, his vampire-enhanced sight easily able to see through the thick clouds of fog pouring through the room. It was crowd that would make his mission difficult, the bodies writhing together so tightly that he wasn't sure where one person ended and the other began. He ran his fingers through his hair in agitation, causing the ends to stick up in a wild fashion that, he noted with dark amusement, would only serve to make him fit in better amidst the visitors of Pandemonium.

A normal man in his forties would be labelled a freak or a child predator if he tried to enter the all-ages club. Simon, however, stood out only for his lack of dyed hair and sobriety.

The joys of being forever young, he thought, though he didn't feel joyful in the slightest.

He saw a flicker of gold in the corner of his eye, a bright beacon through the haze of swirling bodies and foggy smoke. He smiled.

"Got you," he whispered, and set off on his chase.

XxX

He hadn't been doing anything of importance when he got the call from Clary. Halloween was a bitter day for him; probably had something to do with all the adorable little children running around in billowing black capes and plastic fangs. He had been reading an old graphic novel, studiously ignoring the sharp knocks on his door from hopeful trick-or-treaters when his cell phone buzzed in his pocket.

"Simon, I need your help," Clary said immediately upon his answering. He rolled his eyes.

"Hello to you too, Clary!" he said with false cheeriness, "Oh, I've been doing great, thanks for asking-"

"I don't have time for small talk," she said, and it was only then that he noticed the quiver in her voice, "Triss is missing." Simon held back a sigh and set his graphic novel on the coffee table, knowing without any measure of a doubt that his quiet plans to stay in and do nothing this Halloween were now shot to hell.

"What happened?" Simon asked, picking up his shoes from where he had kicked them off earlier in the day and sliding them back onto his feet. He waited for Clary to speak, for a moment hearing only the crackle of static and silence on the other end.

"I don't know," she finally said, her voice flat in a way he recognized as her trying to hold back tears, "She's been in a bad mood for the past few days. I've just been giving her space, and then today I tried to talk to her about it, but it didn't go so well. We got into an argument and she ran out of the house before we had a chance to to work things out…" Clary trailed off and Simon suddenly understood.

The last time Clary had stormed out of the house after an argument with her mother, Valentine had attacked and Jocelyn had almost died. Now Clary was a mother herself and she was terrified that something bad would happen to her baby. With Jace being away in Idris doing Clave business, Clary was probably a nervous wreck.

"Don't worry Clary, I'll help you look for her," he said gently, "After all, I… I am her godfather."

XxX

Triss saw him coming almost immediately after he noticed her. He could tell by the way her body suddenly tensed up, like a bloodhound that had just gotten a scent. She turned around slowly until she was staring straight at him, her green eyes (so like Clary's, he thought) meeting his from across the room. She began to move towards him, navigating through the crowd with a catlike grace that made some of the dancers stop mid-movement to stare as she walked past. Simon could understand this. At sixteen years old Triss was radiantly beautiful with long, wavy hair the same shade of brilliant gold as her father's. She was small, as small as Clary had been at that age, with a scattering of starry freckles across her nose and cheeks. She looked so much like her mother that for a moment Simon was lost in the wave of memories that hit him full force, of him and Clary and what could have been.

"Wow, Mom called out the big guns this time, didn't she?" Triss said with a smirk, interrupting his thoughts and reminding him that it wasn't just her father's hair that she had inherited. He frowned at her and crossed his arms in a way that had never failed to make her guiltily apologize as a child. This time, however, she just laughed. "I'm sixteen, Uncle Simon. That doesn't work anymore." She paused thoughtfully. "Well, it might have worked if you actually looked your age, but you're perpetually seventeen. You're more like a peer than an authority figure."

"You could at least try to make me feel important," Simon grumbled, uncrossing his arms, "Now come on, I need to take you home." Triss ignored him but sidled closer, invading his personal space in a way that made him decidedly uncomfortable.

"Oh, but you are important," she said in a husky voice, brushing her fingers up and down his arm in a distracting manner. Simon gaped at her. Now, he had never been an expert at reading girl's intentions, but age- and vampire super-senses- had given him a better understanding, and it very much seemed like Triss was… flirting with him.

Oh, God.

I changed this girl's diapers, he thought, slightly sickened, and he quickly pushed her away from him. "What are you doing?" he hissed. Someone jostled into him and he was reminded, suddenly, of where they were. He grabbed her hand and dragged her to the far end of the club, where he knew a door to a storage room was. Checking to make sure no trysting teenagers were inside and finding it safe, he slipped through the open door, his blonde shadow following quietly behind him. She surveyed the dusty room, boxes stacked haphazardly in the corner and wires scattered across the floor.

"Oh, are we going to do this here, when anyone could walk in?" she asked, suggestively raising her eyebrows, "Kinky."

Simon hissed, an inhuman sound that made her flinch in surprise. "Stop it," he said forcefully, "Whatever you're trying to do, you need to stop, Beatrice. For G-" he choked on the word suddenly, forgetting in his anger that he, in his damned state, couldn't speak God's name. Triss watched him with wide, wide eyes, and he noticed for the first time how tired she looked. She was pale, and the purple shadows smudged under her eyes reminded him uncomfortably of bruises. She looked so small and childlike that he wanted to sweep her up in a great bear hug the way he did when she was a child, to spin her around quickly in the way that never failed to make her giggle uncontrollably.

Of course, at the rate things were going, she would probably take that as an invitation.

"I'm sorry," she said unexpectedly, her voice very quiet, "I shouldn't have done that. I just…" she trailed off and sniffled. Simon was horrified when her eyes filled with tears. "I was just trying to forget how I felt."

"Oh, Trissy," Simon said, and this time he gave into his impulse to hug her. She practically fell into his arms, barely managing to stick her face in the crook of his neck before bursting into tears. Simon rubbed her back and made soothing noises. He would never cease to be amazed by the strangeness of Shadowhunters; he'd seen her kill demons with the deadly efficiency of an assassin, but she still would cry like a normal teenaged girl, when the occasion called for it.

He waited until her sobs turned to soft sniffles before he spoke. "Do you want to tell me who he is, Trissy?" he asked softly. She froze in his arms and looked up at him suspiciously, causing him to laugh. "Sweetheart, you're not the only teenager that tries to forget their feelings for one person by starting a relationship with someone else." She had the decency to look abashed.

"I really am sorry," she told him, "I was just sad, and dancing didn't really help, and then you showed up and I figured that if I tried to start something with you it wouldn't be so bad because I already love you. You know? But I guess that was stupid, because I love you in a very parental way." She laughed bitterly, rubbing the tears off her face with her hand. He saw the inky marks that covered the skin of her arm and shrugged.

"It's my curse to be forever seen by the Fray women as nothing more than family," he said lightly. Her eyes slid up to his forehead, where they both knew the Mark of Cain hid beneath his hairline.

"I wasn't aware that was a side-effect," she said dryly. Simon laughed, and was pleased to see a small smile appear on her face.

It was moments like this that made Simon hate what immortality had made of his life. If he hadn't become a vampire he would have been middle-aged by now, with a family and a mortgage and a secret porn stash hidden in the garage. He would probably have grown to be portly and bald, but that would have been worth it to have a wife and children of his own. He loved kids- there had been times that Clary had had to practically rip an infant Triss from his arms- and he was good with them, too. He would have been a good father.

But he would never get that chance.

"Max asked me to be his parabatai last week," Triss said abruptly. Simon raised his eyebrow.

"Isabelle's son?" he asked, thinking of the boy who had grown to be as beautiful and deadly as his mother. He had always found it amusing that the kid, for as similar as they were in looks, was so drastically different from Isabelle. He was respectful and quiet to the point of shyness, and spent so much time in the library reading that Isabelle would make jokes about needing to get a blood test to see if the hospital had accidentally given her the wrong child.

(Of course, Simon considered it a blessing. As one of her many ex-boyfriends, he could safely say that the world could only handle one Isabelle Lightwood. And even then… one was pushing it.)

"Why is that bad?" Simon asked, "Isn't that supposed to be a good thing? It means he trusts you with his life." Triss grimaced.

"Parabatai…" she spat out the word, "It's against the Law for someone to love their parabatai, Uncle Simon." His eyes widened comically.

"Oh," he said, "Ohhh." She nodded dejectedly.

He stood very still, not quite sure how to process the overload of information. It was almost okay when his goddaughter was attempting to seduce him, strangely enough (that could easily be explained by some sort of demonic possession or another experiment-gone-wrong courtesy of Magnus Bane), but Simon felt almost hopelessly sad in the face of the discovery that she was in love. His little girl- the one he had carried around piggyback through the city, the one he taught to read comic books and to tie her shoes- was all grown up.

Simon had never felt so old.

"Well, obviously you can't agree to it," he told her. She looked at him in surprise, green eyes wide. "What you need to do, Triss, is tell him how you feel." He held up a hand to stave off her protests. "Now, and you can ask your father about this because I'm sure he'd love to tell you how hilarious it was, but I have experience with confessions of love to childhood friends gone wrong. It sucks. You'll be miserable. You'll think that you will never love again."

"Did anyone ever tell you that you should look into a career as a motivational speaker?" Triss asked, "Because I for one think that you'd be excellent at it."

"Hush, you," he said, "But things do get better. The world doesn't end just because they don't love you back, and maybe you'll discover that it wasn't that kind of love in the first place, like what happened with your mother and I. Or maybe, just maybe, you'll get lucky." Triss cocked her head, curious as a cat.

"What happens if you get lucky?" she asked. Simon grinned.

"They love you back," he said simply. Triss smiled then, slow and brilliant, and he grinned in return. "Now scoot home, munchkin. Your mom is worried about you and you have a love confession to make." Triss nodded and bolted through the door, but not before giving him a crushing hug. "And never tell your father you tried to seduce me!" he yelled after her. He heard her laugh and smiled, happy that he had managed to improve her mood. The door closed.

But the laughing continued.

Simon whirled around, fangs sliding out, and was surprised to see a girl standing in the corner of the room who had certainly not been there before. She was pretty, if not striking like Isabelle or bright like Clary, with brown hair that curled slightly at the ends and intelligent grey eyes. Her clothing was well-worn and old-fashioned, and something about the way she carried herself made Simon think she was much older than she appeared.

Not that he was one to talk.

"That was a very nice thing you just did," she said. There was a pleasant lilt to her voice. "Lesser men would have taken advantage."

"Well, I'm not really a man," Simon said, taking a gamble, "But I'm guessing you already knew that."

Her grin widened and he knew he had hit the nail dead on the head. "You are clever," she said with approval, "Excellent. You will need to be, Simon Lewis." She walked to the door, patting his cheek fondly as she passed him by. "I will stay in touch." He blinked in surprise, but when he opened his eyes he was shocked to discover that she had vanished.

Simon stared at the space the mysterious girl had been, nervous apprehension running down his spine.

"Why," he asked to the empty room, "Do I always get myself into these situations?"

The room didn't answer, but Simon had the uncomfortably feeling that someone had heard him… and was amused.

XxX

A/N: Hi! Thanks so much for reading. This was a real adventure to write, so I hope y'all enjoyed it. I'm hoping to make this a drabble collection of Simon's life as an immortal teenager, since I feel like that would be quite the adventure. The character of Triss basically wrote herself; I really enjoyed how she could be snarky at one moment but vulnerable the next. I picked the name "Beatrice" for a few reasons; Clary and Jace, for one, have all their Dante chats, and Beatrice is an important character in the Divine Comedy. Beatrice is also a character in Much Ado About Nothing known for her wit. Both fit very well for the girl I had in mind.

If I keep this drabble collection up (and if I get reviews asking me to!) I might write something about Triss and Max (who Isabelle named after her little brother, of course) because I feel like that would be pretty darn cute to see.

I always thought it would be interesting to see how Tessa and Simon would interact. Don't think that it was an accident that they first met in the Pandemonium Club.

Please, please review! It would seriously brighten my life!