Chapter Text
1820
Gregory Bridgerton was finally home after his first year at Oxford. After attending Eton College and receiving a rigorous classical education, he enrolled at university to continue studying the Classics. While he enjoyed Latin and Greek literature, he found himself especially drawn to philosophy and ancient history.
As the fourth son, Gregory wasn’t destined for a title or even a fraction of the responsibilities his older brothers carried. Still, he took his studies seriously. He didn’t have Benedict’s artistic talent or Colin’s gift for writing, so he believed the best way to stand out—without a title or a creative calling—was to become a scholar or intellectual.
He poured himself into that goal during his first year. Most notably, he joined the Oxford Union. That decision didn’t sit well with Anthony, who had spent most of his life avoiding politics and couldn’t understand why Gregory, who had no future in Parliament, would waste time debating it for fun. Gregory understood that Anthony only wanted him to enjoy university without trying to shape his entire future around it, but that simply wasn’t in his nature. The Union gave Gregory a sense of independence and a space to explore his own ideas.
Overall, he had a good first year. He felt comfortable at school, as though he had something to contribute. Now, at nineteen, what he dreaded most was attending his first society ball. He’d spent so much time among peers at Eton and Oxford that the idea of standing in a room full of eligible young ladies felt foreign. Gregory wanted to marry someday, but he wanted to be more prepared to take care of his wife and his home. He also knew logically that few would seriously consider him—he was too young and still in school—but the Bridgerton name still made him a target for matchmaking mamas. His brother Colin had already set an inconvenient precedent by marrying young when he returned from his first tour already wed to Miss Edwina Sharma, all the way from India.
Anthony had been livid at first. Colin had barely escaped his engagement to Marina unscathed, and to come back married—without so much as a warning—had seemed wildly irresponsible. But he eventually came around, especially once Edwina’s older sister Kate moved to London with them. Apparently, Colin knew exactly what he was doing when he suggested Kate join them, because not long after, she and Anthony were married.
A couple of years later, Francesca married and moved to Scotland, where she still lived. Their mother, Violet, had since relocated to a dower house, along with Eloise and Hyacinth. And that’s where Gregory was now bound to spend his summer, escorting his mother and sisters to various social events.
Hyacinth was still a year away from making her debut, while Eloise, now twenty-four, was entering her sixth season in the marriage mart. It wasn’t for a lack of suitors. On the contrary, she had received plenty of proposals over the years. But Eloise was a self-declared spinster who dreamed of the day Anthony would finally purchase a home in the country for her and her best friend, Penelope, to share.
Penelope Featherington.
If there was one thing Gregory was looking forward to this summer, it was spending more time with her. He’d known Penelope for most of his life—and, truthfully, had harbored an affection for her for just as long. The turning point came during her third season out, the year before he left for Eton. She and Eloise had been estranged for much of that year, but it was also the season Francesca debuted, and Gregory overheard that Penelope was seriously looking for a husband.
He remembered feeling an odd sort of jealousy that season, even though he was just a boy. Penelope had started wearing her hair differently and appeared in new gowns with soft, elegant colors that made her look exceptionally beautiful. But instead of simply admiring her, Gregory felt a quiet sadness. Not just because he was jealous, though he was, but because it pained him to see her changing herself in order to be noticed.
Perhaps it was due to the fact that he was young, but he quite missed the brighter colors she used to wear. They matched her easy smile and the excitement he always felt when she walked into a room.
One evening, he overheard his mother mention that Penelope was expecting a proposal. He still remembered the way his body went numb, the sting of disappointment settling in. It felt so final, so unfair that he’d never even have a chance. But, thankfully, Penelope had been reluctant from the start. She never wanted to marry purely for convenience, not without the hope of love. And when Eloise, despite their falling out, saw that her friend was preparing to make a decision against her heart, she put aside their differences. She reminded Penelope that she didn’t have to marry if she didn’t want to.
Just like that, they renewed their joint vow of spinsterhood.
As far as Gregory knew, Penelope had returned to her familiar place at the edge of the ballroom, standing beside Eloise and avoiding attention whenever she could. He wasn’t sure of her motivations—whether she was truly avoiding marriage or simply disillusioned by it—but he was determined to find out. More than anything, he wanted to spend time with her now, as a man, and perhaps erase any assumptions she might hold about him.
Their mother had always told him and his siblings that the key to a true love match was friendship and finding someone whose company you genuinely enjoyed. Gregory didn’t remember much about his father, but he remembered enough to know he had always been present. It made sense, then, that their parents were friends. They truly derived satisfaction from spending time with each other.
Gregory often felt like he already knew everything about Penelope, from her favorite book and dessert to the flower she always paused to admire in the Bridgerton gardens. But she didn’t know him. Not quite. Not as the man he was becoming at least—the university student, the budding intellectual, the person who thought of her more often than he liked to admit.
He wanted her to meet that man.
Mr. Gregory Bridgerton.
—
As tradition dictated, the opening ball of the season was hosted by Lady Agatha Danbury. This year’s theme was a patriotic tribute to the Crown, celebrating the official ascension of King George IV. The ballroom had been transformed into a lustrous homage to the monarchy, with royal crests and portraits displayed throughout. One in particular—the late Queen Charlotte, a dear friend of Lady Danbury’s—was wreathed in laurel and roses. The rest of the floral arrangements featured white roses and violets, and golden and ivory drapery flowed from the ceilings and balconies. No detail had been overlooked, and no expense spared. It was, as always, a statement of grandeur and loyalty.
Gregory entered the ballroom with Violet on one arm and Eloise on the other. He must have looked more anxious than he realized, because both women rested their free hands gently on his arm, a silent gesture of reassurance. He smiled at them, grateful, before they began their descent down the grand staircase.
Once they reached the floor, the three of them remained close.
“I thought Anthony would be here by now,” Gregory said, scanning the crowd for his brother.
“He stopped coming after the Queen passed away a couple of years ago,” Eloise replied. “Apparently, she was the intimidating one. But you can be sure he’ll attend every single one of these once Hyacinth debuts next year.”
“I’m sure he’ll make an appearance,” Violet added gently. “It wouldn’t be wise to neglect showing support for the new King.”
Gregory nodded, still glancing around the room, his gaze drifting from one cluster of guests to another.
It didn’t take long for the familiar tap of Lady Danbury’s cane to echo across the ballroom floor as she approached.
“Good evening, Bridgertons,” she greeted them with her usual commanding warmth. “Always a pleasure to see you. And you, Mr. Bridgerton—looking very dapper tonight. A proper gentleman.”
“Thank you, Lady Danbury,” Gregory replied earnestly. “The room looks exquisite.”
“It is the first ball of the season,” she said proudly, “and I take great pleasure in leaving the rest scrambling to measure up. It makes things far more interesting. And considering it’s your official season out in society, I had to make it nothing short of remarkable.”
He wasn’t surprised that she knew. She had always been like a grandmother to him, or at least the closest thing he’d ever known to one.
“And here I thought this was all for the new King,” Gregory said lightly.
Lady Danbury chuckled, clearly pleased. “Charm and looks.”
She gave him an appraising once-over before glancing meaningfully at Violet, then delivering a pointed look in Eloise’s direction.
“After all these years, it seems we have yet another Bridgerton diamond on the marriage mart.”
“What a wonderful idea that would be,” Eloise said with mock enthusiasm. “Instead of displaying young women like cattle at an auction, we should be parading the eligible men. Although I’m not sure how eligible this one is if he’s still in school.”
“You wound me, sister,” Gregory replied, feigning offense. “I would very much like to get married one day, but I’m not in a rush.”
“And you have no reason to be, my dear boy,” Violet said warmly. “You should wait for love. Just like Eloise is.”
Eloise rolled her eyes, but Gregory and Lady Danbury couldn’t help but laugh.
“Well yes,” Lady Danbury said, eyes twinkling, “by all means, wait for love. You are, after all, afforded that luxury. But a handsome young man like yourself should still enjoy the season. I expect to see you on the dance floor—and with someone who is not your sister.”
“I don’t believe that will be an issue,” Gregory replied teasingly. “I’m quite fond of my well-functioning feet.”
Eloise elbowed him, earning another chuckle from Lady Danbury.
“Good,” she said, her cane tapping once on the floor. “There are plenty of formidable dance partners for you to choose from.”
As if summoned by her words, Penelope Featherington appeared from behind a column. Gregory’s eyes instantly landed on her. She was in a fine sapphire blue dress, with her hair styled in loose curls to one side. He hadn’t seen her in a while and was definitely taken by her sight. His mother must have heard his heart beating a little too fast upon seeing her because she offered one of those knowing smiles to him.
Eloise instantly let go of his arm and all but ran to Penelope. His mother still held onto him as they walked in their direction. “Penelope is a great dancer.” Violet nudged him gently.
“I know.” He smirked. “We used to practice the steps together when I was younger.”
“I remember.” Violet replied.
—
Penelope was deep in the middle of eavesdropping on a particularly juicy bit of gossip about how Lord Livingston had failed to pay his daughter’s dowry to Lord Stanton when her attention shifted.
Gregory Bridgerton descended the staircase, flanked by Eloise and Violet on either side.
Eloise had told her he was coming to London for the season, and Penelope had been quietly looking forward to seeing him. Gregory had always possessed such a gentle nature. She still remembered how nervous he’d been before setting off for Oxford, and she often found herself wondering how he was doing, hoping the world hadn’t dulled his sweet spirit.
What she hadn’t expected was how different he looked now. His hair was longer, soft and wavy like Colin’s, though not quite as dark. He looked older, but not much. It wasn’t something in his features so much as in his eyes. Gregory had always been playful growing up—more of a daredevil than anyone else in his family—but even then, he’d carried a certain seriousness that set him apart. It seemed to have deepened since she last saw him.
Before Penelope could dwell on it any further, Eloise appeared at her side and pulled her into a quick hug.
“There you are,” Eloise said, releasing her. “You had me worried.”
“Where else would I be if not hiding from my mama?” Penelope chuckled.
Eloise frowned in sympathy. “How is she tonight?”
“A little better. Phillipa’s expecting again, so I believe she’ll be happily distracted with Philomena and Phineas over the next few months.”
“Great news,” Eloise said with a grin. “We have work to do this season.”
Ever since their reconciliation, Eloise had been helping Penelope with the Lady Whistledown columns. Penelope still had the final say, of course, but she quite enjoyed sharing the workload with her friend. They had to attend these endless social events anyway, so they might as well make them entertaining.
Penelope was just about to reply when Gregory stepped in front of them.
“Good evening, Miss Featherington,” he said with a polite bow. “You look very lovely tonight.”
She smiled, caught off guard, a faint blush blooming on her cheeks. It was hard not to blush when he was looking at her so intently.
“Oh, don’t you dare, Gregory,” Eloise interjected sharply. “You are not using Penelope to practice your subpar flirting skills.”
Gregory’s eyes widened in surprise, clearly not expecting the accusation. Penelope couldn't help but tease him too.
“Is that what it is?” she said, feigning offense. “So you don’t truly believe I look lovely?”
His face went pale, and he began to stammer, clearly scrambling for a response. Eloise tried—and failed—to smother her laughter behind her hand. Penelope almost felt bad for teasing him.
But Gregory recovered quickly.
“Do you really believe everything Eloise says?” he asked, his voice smoother now, a confident smirk tugging at his lips. “I wouldn’t use you to practice, Miss Featherington. If anything, I would’ve practiced just to be able to speak to you.”
Penelope blinked, mildly surprised by the sincerity beneath the charm. Eloise, however, rolled her eyes.
“No rehearsals needed, Mr. Bridgerton,” Penelope said, her smile softening. She noted the way his expression remained serious, even as he returned her smile.
“Would you do me the honor of a dance?” Gregory blurted out.
Eloise blinked in disbelief, while Penelope was too stunned to reply right away.
Penelope hadn’t taken the dance floor since her third season and near-engagement. And now here was Gregory Bridgerton, asking her to dance—not in the safety of a drawing room, but here, in front of the whole of society.
“I’d be honored,” she said at last, “but it’s your first dance.”
“I know I’m only a fourth son with very little experience,” he replied with a smile, giving her a light wink, “but I did have excellent tutors growing up.”
Penelope laughed softly.
“That’s not what I meant,” she said. “Your first dance shouldn’t be with a spinster and a wallflower.”
She didn’t say it with sadness, just concern. Concern for him . For how it might look.
“I think my first dance should be with whomever I want,” Gregory said, without hesitation. Then, clearing his throat, he added more gently, “If she wants it too, of course.”
Eloise was still too confused to say anything, but Penelope finally gave a small nod of agreement.
Gregory straightened, offered his hand, and Penelope took it. He led her to the dance floor just as the opening notes of the quadrille began to play and couples arranged themselves into squares. Her heart fluttered unexpectedly as her gloved fingers curled more tightly around his.
The dance was graceful but too fast-paced to allow for real conversation. Yet words didn’t matter at that moment. What mattered was how the couple moved together, how instinctively they responded to one another. That was the true measure of compatibility. And Gregory and Penelope danced perfectly attuned, drawing admiring glances from onlookers—most notably Violet and Lady Danbury.
After that night, the rest of the season seemed to carry a rhythm of its own. They found each other in ballrooms, soirées, musicales, and operas—always gravitating toward one another and seeking the other’s company. When Penelope visited Number 5, they often ended up playing cards, their conversations stretching long with Eloise and Hyacinth chiming in along the way.
And so, the roots of their years-long acquaintance deepened into a beautiful friendship they would cherish for many years to come.