Prompt: Alison or Stevie goes to Henry for dating advice.

I thought this was kind of funny considering that I headcanon Alison as being gay so I'm not really sure what this is but I hope you enjoy it.

Alison bit her lip, squaring her shoulders as she hesitated on the steps of the Georgetown brownstone she'd been calling home since she was fifteen. She could see her dad, sitting alone in the den with a book open in his lap, and she knew that this was her chance. She'd been trying to get Henry alone for close to a week now, and she knew she had to seize the opportunity while she had it, before her bossy big sister or annoying little brother or well-meaning Mom showed up and tried to help. No, this was a conversation that Alison specifically needed to have with Henry, because her dad was the most romantically successful person she knew, and Alison desperately needed advice.

If anyone knew how to romance a girl, Alison figured it had to be Henry McCord.

After all, her mom still looked at him like he hung the moon in the sky just for her, and that was after three decades and as many children. She was sure that if he could do that, he could help her get a date with the pretty blonde in her drawing class. Alison took a deep breath and then forced herself forward. This was no time to debate over it.

"Dad?" she asked, catching Henry's attention. He glanced back at her.

"Hey, Noodle," he greeted her. "What's up?"

"Well…" Alison began, slowly sinking down onto the couch beside him in the den. "I was just wondering if you could help me with something."

Noting her cautious tone, Henry closed his book and set it aside, turning his full attention on his middle child.

"Of course," he replied. "What is it?"

"I need your advice on how to be romantic," she blurted out, and Henry paused for a moment, meeting her deep, soulful brown eyes.

"Being romantic?" he repeated, and Alison nodded.

"Look, it's just that...I don't know, I grew up knowing how it works to play the princess role. I got that from Disney movies and rom-coms," she told him. "But I'm realizing that I have absolutely no idea how to do it the other way around and, you know, I'm not exactly in a position to just sit back and wait for a prince to sweep me off my feet."

"Is there something in particular prompting this?" Henry asked her, and Alison sighed.

"It's Caroline," she said.

"The girl you had that presentation with?" Henry asked, hoping that he'd managed to recall that correctly. Alison nodded her head.

"Yeah, that's her," she confirmed. "I really like her, and I want to ask her out, but I just don't know how to do it, and…" she trailed off, and Henry stayed silent, waiting for her to gather her thoughts.

"I'm asking for your help because you're the most romantic person I know," she admitted. "And you got Mom to love you for a really long time so you must be doing something right."

Henry couldn't help but laugh at that, thinking to himself that if only it were that simple, he would be in good shape.

"What?" Alison asked.

"Ali," Henry began, "it's not like that. You can't just whip up some romantic date night or grand gesture and have that be enough."

"What do you mean?" Alison asked slowly. Henry looked over at her, and for just a moment he saw the inquisitive, shy little girl with the softest dark curls who was always hiding behind her confident big sister. It felt like it had been just yesterday that he'd scooped that little girl up in his arms with such ease and twirled her around. It never failed to make her laugh, and Henry adored the sweet sound of little Alison's laughter. He adored the sound of her laughter now, too, this sophisticated, adult version of the little girl with the dark curls. He smiled slightly at her, reaching out to tuck a strand of her hair behind her ear. His heart ached in those moments; he wanted nothing more than to protect her sweet soul from all the dangers of the world, including that of heartbreak.

"Honey, relationships can't be built on that kind of foundation," he told her gently. "If you build something on the foundation of showmanship, even showmanship rooted in genuine feelings, it's going to crumble. You have to start slowly."

"I don't really understand," Alison said.

"Okay, you know why your Mom and I work the way we do?" he asked. She shook her head.

"Why?" she asked.

"Not because I was romantic," Henry chuckled. "Because we built a foundation. I got to know her. I gained her trust. She gained my trust. We grew to love one another, and yes, there was romance but not the kind you see in the movies. It was a lot more subtle than that, and it all started with that foundation of mutual trust and respect for one another as individuals."

"So...no grand gestures is what you're saying?" Alison asked, and Henry smiled as he reached out to wrap his arm around her shoulders.

"I'm saying take it slow. Don't jump off the high dive before you test the waters. Be her friend first, get to know her, and take it from there."

"Okay," Alison agreed. She looked up at him and smiled.

"You give pretty good dating advice," she said, and Henry grinned at her.

"Well, I did okay on the dating scene," he replied, and she laughed as she rested her head on his shoulder.

Later that evening, as Elizabeth and Henry moved easily around one another in their nightly routine of getting ready for bed, Henry glanced over at his wife. No matter how familiar he was with her, she never failed to take his breath away. He'd always felt he had gotten luckier with Elizabeth than he'd ever deserved; in fact, he'd wondered more than a few times over the last three decades if the other shoe was ever going to drop. It all just seemed too good to be true; even on their worst days as a couple, he had adored Elizabeth, and counted himself incredibly lucky to have her at his side.

"So Alison asked me for dating advice today," he said. Elizabeth, seated at her dressing table, glanced over her shoulder at him.

"She did?" she asked. "Why?"

Henry chuckled.

"Because I know how to romance a girl, apparently," he told her, and she laughed.

"Are you?" she asked. Henry smiled as he approached from behind and wrapped his arms around her, dropping a kiss to the top of her head before she leaned her head back against him and smiled up at him.

"Well, I must have done something right," he said softly, leaning in to press an upside-down kiss to her lips.

"So what did you tell her?" Elizabeth asked as she disentangled herself from him and moved toward her side of the bed.

"I told her that it's not about romance," he replied honestly. "You know, that it's about building a foundation of trust."

Elizabeth looked over at him and smiled. In that moment, she wondered how on earth she'd gotten so lucky.

"I love you, Henry," she said, knowing that would be enough to get her point across. Judging by the way his hazel eyes softened as he leaned in close and drew her in with a hand on her cheek, fingers burying in her hair, Henry got the message.