Chapter Two: A First Date

Logan woke up to the sound of shattering glass just a few feet away from his head. He rubbed his eyes for a moment, trying to wake himself up fully before sitting up on the couch. He glanced over at his friends in the kitchen. "Who broke something?" he mumbled, still half asleep.

Finn let out a soft laugh. "Well, Colin and I made a bet."

"A bet?" Logan questioned.

"Yeah, a bet on who could wake you up first. I won," Finn said with a wide smile on his face.

"By breaking the glass? The one Rory picked up in Italy last summer? He really liked that glass! I feel like I should win the bet!" Colin debated.

Logan chuckled. "Finn, you have to tell Rory." He got up from the couch and made his way into the kitchen, pouring himself a glass of water. "I really don't want her to be angry. But, boys, I have some news."

Finn hopped up onto the countertop while Colin began cleaning up the broken glass. "Is it that you took young Hayden's innocence?" Finn teased, giving his best friend a wink.

Logan shook his head. "No, nothing like that." He wouldn't talk about that with them anyways. "Hayden and I have a date tonight."

"A date?" Finn exclaimed. Then he straightened up and shouted, "Young Gilmore is eighteen! Are you going to try to win her over?"

Logan couldn't help but smile. "I just hope I don't mess up our friendship."

"You won't," Finn assured him. "Rory has two big brothers who will make sure you're on your best behavior."

"Since when does she have big brothers?" Logan turned around and leaned against the counter.

"Us, of course!" Finn exclaimed, his tone serious. "Colin and I consider ourselves her big brothers. We care about her, we love her, and we don't want to see her get hurt."

"I won't hurt her," Logan stated firmly.

"We know," Colin chimed in. "I've seen how much you've cared for her since she was twelve. Do you remember that night when she showed up at your house, crying after her parents had a big fight?"

Logan nodded, a soft smile forming as he recalled the memory of the broken girl seeking solace. "I gave her a hoodie and we watched a kids' movie together. I remember calming her down and her falling asleep against me."

"You made her feel safe and loved that night. You welcomed her into our group," Colin said, proud of his friend. "Even at such a young age, you were falling in love with her."

Logan laughed softly, grateful to remember that pivotal moment. But his thoughts were interrupted by a question. "What did the LDB think of her last night?"

"She impressed them. They all liked her, especially Robert, who was quite taken with how she can handle tequila," Colin answered.

Logan let out a sigh, rolling his eyes at the mention of Robert. While they were all friends, there was some tension there. Logan wasn't a fan at some comment Robert has made about Rory in the past. Glancing at the time, he realized he needed to get ready for his first date. "I need to shower and pick up Rory. Can one of you call the cleaners?"

Finn laughed. "Colin's got it covered!" Logan rolls his eyes, going to his master bathroom as he hears Colin groans.

— Ace —

Rory's nerves were inexplicable. Though she couldn't find any reason to feel nervous or scared, she couldn't help but feel an overwhelming sense of happiness.

She slipped on a lightweight cardigan over her dress, paired it with black sparkly flats, and grabbed her purse. Making her way to the common room in her dorm, she noticed her date already dressed in a suit. "You're early," she remarked. "And didn't knock."

Logan shrugged. "You, dear, shouldn't keep your door open. Where's your bag?"

Confused, she looked at him. "What?"

"Your bag. Your overnight bag. Where is it?" he clarified.

Her head tilted slightly, a small frown forming. "Does the rule still apply?"

The blond nodded. "Of course the rule still applies. I didn't think I would have to remind you, Miss Rule Follower." Rory raised a finger, walked to her bedroom, and returned minutes later with a Louis Vuitton overnight bag. The bag is a present from Colin from Christmas last year and with the friends she had the bag has truly come to great use. "Good job, my darling."

Curiosity bubbling up inside her, she couldn't resist asking, "Are you going to tell me where we're going on our date?" Her fingers brushed against the bag's handle.

Logan leaned over, taking the bag from her hands, and smiled softly. "Rory, surprises are better. We've talked about this."

"Am I underdressed?" she inquired, suddenly feeling that the dress she was wearing didn't match the suit that he was wearing.

He grabs her bag out of her hand. "No, not at all. Come on, we're running late," Logan said, his grin widening.

— Ace —

Forty-three minutes later, the expression on Rory's face was pure surprise as he stepped onto the yacht. "I thought we were going to dinner?" she questioned.

"We are," he confirmed, he sets down both his bag and hers on the chairs.

"On the boat?" she clarified.

"Yes, that's right," Logan replied with a soft smile. "Come on." He interlaced his fingers with hers, leading her to the front of the boat. At a well-dressed picnic table, he set out two glasses and poured champagne, kissing her cheek after she took her seat.

"I'll be right back. I need to inform the captain that we can set off now," Logan informed her, receiving a nod in response. Rory watched as her future fiancé walked away, then closed her eyes and took a deep breath, savoring the peacefulness of the moment. She's been on boats like this before but it was different when there were just the two of them on it, excluding the staff. When Logan returned and kissed her cheek again before settling down in front of her, she couldn't help but blush.

"Have I ever told you how absolutely radiant you look?" he complimented.

She blushed further, momentarily hiding her face. "Thank you. You don't look too shabby yourself, you know?"

He chuckled softly, his smile gentle. "Thank you, Ace. I have to admit, I was a little nervous about this."

"About this date? Is that why you went all out?" Rory offered him a small smile, one she had learned from Logan over the years.

"Partly. I wanted to make it special because you deserve it, Ace. We've both had to deal with the burden of our arranged marriage contracts. You deserve an amazing first date," he conveyed.

Dinner and dessert passed swiftly, with the sun setting majestically over the ocean. Logan had plotted a route for the boat, taking them through Gardiner's Bay and back. They would return to the boatyard around eight in the morning.

Throughout dinner, their conversation covered a range of topics. Rory inquired about Logan's plans once again, and he reassured her that he would stay in constant communication while they were away. Logan, on the other hand, asked about Rory's plans for her first year at Yale and reminded her to have some fun. He mentioned that Stephanie, Rosemary, and Evie were still at Yale, causing Rory's laughter to imprint itself in his memory. She promised that she wouldn't allow herself to be consumed solely by her studies, that she would have fun and she made him promise her to stay safe and enjoy himself.

Dessert was a frangipane tart made with strawberries and blueberries. A dessert Rory fell in love with when Finn made them drunk from memory a few years ago. She takes the first bite, her eyes moving to Logan's. "These are Finn's." It was a statement, not a question.

"I know how much you love them. Noone appreciates Finn's baking as much as you do, I thought it would be the perfect dessert for our date." He explains, taking a small bite of his. His friend really did have a talent for baking.

Rory could feel her heart swelling at his words. He really was a gentleman. "Thank you for always making me like the most important person in the world."

"You don't have to thank me." The words come out of his mouth as a whisper.

— Ace —

As she let herself relax, she became aware of his presence enveloping her from behind. His arms slipped around her front, pulling her closer, and he delicately rested his head upon her shoulder. The moment felt surreal, with the city lights twinkling in the distance, the soothing sound of the ocean waves crashing against the yacht, and the vast expanse of stars shining brightly above them. Breaking the silence, he asked softly, "Dinner?"

"Was a success," she replied contentedly.

"And dessert?" he inquired.

"Oh, I fell for it. Head over heels," she responded with a hint of humor. She put a note in her head to remember to thank Finn. This was undeniably the best first date she had ever experienced, or any date for that matter.

But Logan, perceptive as ever, sensed that something was still on her mind. After all these years, he could read her like an open book. She turned away from the water to face him directly. "Besides what the future has planned for us, you're leaving tomorrow. What's going to happen to us?" she asked, her voice tinged with concern.

Logan made a contemplative expression. "I plan to visit you several times during the year, and we'll continue to talk, write, and send postcards. Maybe you can come out to us at one point. I still want to court you," he assured her. The word "court" caused a blush to crept up onto her cheeks.

"I'm going to miss you," she mumbled softly. "I'm going to miss you a lot."

"I'm sorry," he murmured, his voice laced with genuine regret. "But I'll miss you too. However, before I leave, there's something I need to ask you."

He reached into his pocket and pulled out a small blue box, the very box that had been burning a hole in his pocket since he slipped it in earlier that afternoon.

Opening the box, he revealed its contents. "Lorelai Leigh Gilmore-Hayden, will you please be my girlfriend?" he asked, his eyes filled with hope and anticipation.