Tamara Fox had been a large part of Tim Drake's life for the better part of two years now. Because of the persistent meddling of one obnoxious reporter, they had become good friends while pretending to be engaged. Later on, he discovered that there were some unintended perks to this situation he'd been forced into. The main benefit he would discover was that since Tam already knew about his double life, but was a "civilian" herself, it provided a much needed outlet over the years to have someone he could spend time with outside of the Incorporation with all its uniforms, masks, and crime fighting. It was nice. It was comfortable. It was normal.
It was a chance to rediscover life beyond the mask.
Somewhere down the line, when Tim wasn't looking (when he wasn't even trying for that matter), he'd started falling in love with the smart, sassy college girl from the good, stable family. Pretending to be a couple for the press and society gossips had somehow turned into the real thing. However, if someone asked him when it all started, when he realized that Tam was more than just a friend, he'd be at a near total loss for words. There were a number of possible moments to choose from...
Perhaps it was during that one December day they shared together during the previous year. It was a seemingly normal winter day that had started with an insane amount of trudging through knee-deep drifts in the snowy wooded acreage around Wayne Manor. At Tam's unusual insistence, they'd spent nearly two hours in the freezing cold gathering enough mistletoe from the surrounding trees to effectively canvas every floor of Wayne Tower, from entrance to penthouse. She'd said she had just wanted to spread a little holiday cheer, but Tim knew that the mischievous gleam in her eyes meant she had something more than cheer on her mind. Still, he didn't have a clue as to what the girl was really up to... That was, until he ran into Bruce Wayne's youngest son right as he was leaving a board meeting.
Damien Wayne and Timothy Drake had nearly collided with one another at the elevator. The younger boy was in a furious, almost murderous rage. The glare he shot Tim might have been intimidating to the elder brother, were it not for the fact that Damien's face was covered with a multitude of varying shades of lipstick prints. Tim somehow managed to hold his composure as he stepped into the elevator to ride it the rest of the way up to the penthouse they shared with the rest of their family. Any hold he had on that composure was lost completely when he later saw the videos from the security cam feeds of Damien attempting to maneuver through the building while trying (and failing) to avoid all the random women caught up in the holiday spirit who ambushed him under the leafy green sprigs.
Far as Tim knew, the little demon never figured out who actually set the whole prank up. When Damien had interrogated him on the matter (after washing off all the lipstick and once Tim was able to look at him for more than two second before dissolving into snickers), he could honestly say that it wasn't his idea. He admitted to being a lackey in the scheme, but not its ultimate mastermind. That honor belonged to Tam, and he wasn't about to give her up to his little brother. After the prank she'd just succeeded in pulling, he wasn't stupid enough to betray her for fear of retribution. Besides, the laughter and memories it gave him had been her very first Christmas present to him.
Maybe the moment in question happened a little later, a month after that when Tim, as Red Robin, had taken a break during his nightly patrol to stop by the piano bar where Tam occasionally played when she wasn't busy with school or work. He knew she played the piano. She told him she'd been playing since she was five. However, he'd never seen her perform before. Out of curiosity, and because it happened to be a slow night for crime, he had Oracle track down the address of the place where Tam played so he could stop by for a peek.
That bitterly cold January night was the first time he'd ever seen her in formal attire. She had worn an elegant black velvet evening gown with immaculate makeup and her hair had been done up exposing her long elegant neck. That night she played Chopin's Nocturnes at a magnificent grand piano. Wrapped in the warmth of the bar and the music, the Red Robin listened and watched while hidden in the shadows of the rafters high above the stage. Tam looked almost otherworldly in the dim mood light of the darkened bar as the passionate strains of music flowed from her fingertips and wound around his heart. He never told her, but that night was the first time she stole his breath away. Especially when she played the piano, he found he could lose himself for hours listening to her music... So much so he had to make it a point never to stop by on nights where he knew he needed to be focused on his work.
Eventually, she learned that he stopped in to listen to her from time to time. She had been so surprised. Not even her family knew that she played. She'd kept it a secret from them for her own reasons. He told Tam where to look, and at the beginning of her sets from that point on she'd glance at that corner of the rafters to see if he was there. She never told him, but the owner of the piano bar said that occasionally, on those nights when Tim secretly visited her, Tam's music would sound more heartfelt and beautiful than normal.
Then again, maybe the moment where everything just clicked was during a stormy spring night just a few short weeks ago, when he stumbled onto the balcony of the apartment she now lived in, just returned from a long mission overseas. Tim was sick from exhaustion and suffering a high fever. He'd come to her home because he promised to see her when he returned. To say that she was upset was an understatement. Still, she'd cared for him, forced him to rest for the remainder of the evening and well into the next day, skipping both work and her classes at Gotham University.
A couple of days later, she made certain to berate him soundly when she was sure he was well enough to stand the lecture and the blows from the pillow she grabbed to beat him with. If he remembered correctly (and fondly), the tirade ended abruptly when the two of them tumbled onto the sofa as he'd tried in vain to disarm her. When they found themselves tangled up in each others' arms, not quite certain how they got there, one thing ultimately led to another...
In the end, it didn't really matter to Tim "when" it all happened. Yes, being around Tamara made him happy, made him feel more like "Tim Drake" than he'd been in years. However, the side of him that wore the mask and the uniform night after night was far from pleased.
That darker, more paranoid aspect of him whispered in his mind with his adopted father's deep ominous tones and warned him, in no uncertain terms, of every horrible, torturous, potentially deadly thing that could happen to her if he continued in this illusion of a relationship. What little sleep he got these days was haunted by the nightmares of the suffering that could come to Tam at the hands of all his worst enemies. It wasn't as if he had to stretch his imagination that far to bring the images to mind. He knew simply from real, first-hand experience. The closer he got to Tamara, the stronger his affection for her grew, the greater and more all-consuming the fears became.
She wasn't like Stephanie or Cassandra or even half the other girls he knew in his life. She wasn't a meta with a collection of natural superpowers or someone trained in a multitude of deadly martial arts. She was just an ordinary girl who went about her normal days without having to worry about fighting super villains or somehow averting catastrophic world-shattering events on a regular basis. How could he, in good conscience, allow her to get even more tangled up in this dangerous life of his?
He'd already lost so many people he loved by horrible, violent means.
And even though a number of them would eventually come back, Tim could often do little more than watch as many of his closest friends and allies died in the line of duty, including the original Batman, Bruce Wayne, himself.
Eventually, after weeks of brooding and analyzing the situation as logically as he possibly could, with a heavy heart Tim Drake decided that for the sake of protecting the woman he'd grown to love he would have to step completely out of her life.