1869 | As the year comes to an end, so does the pregnancy of Hattie Whitledge. On the eve of December 29th, she gives birth to twins: a boy she names Handsome and a girl she names Cupcake. While her husband complains about the "outlandish" names, her persistence eventually wears him down.

1870 | Pumpkin, the third child born into Handsome's family, enters the world. Seeing as Handsome is less than a year old, her birth is irrelevant to him at the time.

1871 | Hattie gives birth to another child, this time a single girl named Sweetie. At less than two years of age, Handsome barely recognizes the significance of another child in the house.

1873 | After his mother gives birth to another girl, Handsome, now three years of age, understands that there is another soul to share attention with. Though not necessarily cranky, he gets frustrated when not given the center of attention at certain times.

1874 | After having pondered on the possibility of gaining a brother throughout the duration of his mother's pregnancy, it's unsurprising that the birth of another sister is met with disappointment. Though upset at first, the four-year-old doesn't shy away from showing his new sister Honey attention when permitted.

1875 | Cupcake shows her first sign of magic. While this is celebrated in the Whitledge household, Handsome cannot help but feel inadequate—despite his father's assurances that his time will come—compared to his twin. He ventures to discover his own first sign of magic, getting into trouble on more than one occasion for trying to force it out of himself.

1877 | The muggle community discovers magic, leading to the Whitledge family to settle into Hogsmeade alongside many of the other magical families. While the sudden move is met with anxiety on Handsome's part, it soon disappears when he realizes everyone around him is also magical. However, it does nothing to soothe his fears that he'll end up a squib.

1879 | Finally, at nine years of age, Handsome's first sign of magic makes an appearance.

1881 | Handsome and his sister receive their acceptance letters to Hogwarts and are shipped off to school in September. His first year is characterized by an intense focus on school work. While he does involve himself in the Leisure Sports Club and Dueling Club, he doesn't hesitate to skip meetings if they interfere with his homework.

1882 | Pumpkin joins Handsome and Cupcake at Hogwarts. Unlike them, however, she is sorted into Ravenclaw (which seems fake but ok).

1883 | Handsome begins his third year and adds Ghoul Studies, Care of Magical Creatures, and Muggle Studies to his schedule. Sweetie also joins them at Hogwarts, but is sorted into Slytherin. He's now taking bets that Darling will be a Hufflepuff.

1884 | The year seems to be going well until tragedy strikes: Handsome's father dies from the laughing plague. After that, on top of the fire that ravages Wellingtonshire in the weeks following, Handsome's mother makes a sudden decision to move the family to the nearby village of Irvingly. Darling begins Hogwarts and is sorted into Hufflepuff, which means the Whitledge family has now invaded all four Hogwarts houses.

1885 | Handsome is named Gryffindor prefect.

Spring, 1886 | Handsome befriends another girl in his year named Madeleine Backus. While their gender and social classes make them an unlikely pairing, the two's personalities mesh well and their interests align. In May, he sits for his OWL examinations.

Summer, 1886 | Over the summer, his mother returns to society after two years of mourning and decides to pursue the healing career she'd put off after marrying. While happy that his mother no longer spends the days drowning in her own sorrows, he doesn't appreciate her decision to seemingly abandon her children.

Autumn, 1886 | The school year starts off with the Sorting Hat getting stolen, which means Honey's sorting is postponed for a solid week. However, when the sorting ceremony finally does commence, she joins Darling in Hufflepuff. Handsome continues his education with Charms, Defence Against the Dark Arts, Herbology, Potions, Transfiguration, and Care of Magical Creatures.

June, 1887 | After his sister instigates a fight with Maddie, Handsome comes to terms with his emotions. Sadly, it proves to be only the beginning of his despair.

July, 1887 | When the Wizarding World Market tragedy takes place, the Whitledge siblings learn that their mother was in the middle of the disaster site. He and his siblings are orphaned, and such a blow leads Handsome spiraling into depression. Alcohol because his choice of coping mechanism, which further leads to him isolating himself from his family out of shame. On a brighter note, he and Maddie do confess their feelings, though do go long periods of time without contacting one another. It is only upon receiving his school letter—his head boy badge included—that he finds the willpower to move forward.

Winter, 1887 | Handsome remains at school for the holidays instead of returning home. Not only does it mean he's spending Christmas by himself, but also his eighteenth birthday.

1888 | Handsome graduates from Hogwarts and, under the influence of his dorm-mate and best friend, joins the Hogsmeade Howlers as a reserve keeper. Tragedy strikes when his grandmother is killed during the Irvingly fog (which eventually moves to Hogsmeade), leaving him with no one to pass the responsibility of his sisters onto. He struggles with alcoholism, though does bounce back—but only when the girls return to school.

1889 | Following the end of the quidditch season, Handsome leaves the Howlers in favor of an internship in the Department of Magical Law Enforcement. He thinks it'll help him "man up" and do something productive with his life— a goal that inevitably falters when Pumpkin dies at the hands at a vampire in July.

1890 | Handsome switches to the Department of Magical Accidents & Catastrophes as an Obliviator, still unsure of where the best place for him to build a career is. It doesn't help that Sweetie seems firm in her intention to pursue the path of an Unspeakable once she meets the requirements. Cupcake has yet to marry, and with Darling less than a year from debuting it seems as though life has no intention of slowing down.