Oliver watched as William's phone buzzed for what seemed like the millionth time. It had started out at the center of the kitchen table, but the vibrations had moved it until it was now perilously close to falling off the edge, onto the floor. Oliver was trying to decide if he should silence it or not when Will came back into the room.

Will checked the screen and a goofy grin lit his face as he typed in a reply to whatever he saw. "Hey, Dad, you know what I really want for my birthday?"

"What?" Oliver responded with his own smile. Fifteen. It was flying by so fast. Will was going to be an adult way too soon. Next year, he'd be able to drive himself wherever he wanted to go and Oliver would probably only see him when he was sleeping.

"I want to go see the Chicago Institute of Art. I've been looking at pictures of it online and it looks so cool. Walt Osmond is going to be there the weekend of my birthday giving a two-day demo. I really want to do it. And it would look really good on my college applications. Plus, we could go to the Navy Pier and maybe check out Wrigley Stadium."

Oliver didn't personally have much of an interest in art, but Will lived for the stuff and the boy seemed so excited it was hard to say no, especially for his birthday. Will gave a cheer when Oliver pulled out his cellphone and started relaying reservation instructions to Mia, his assistant.

"Ooh! You know who else would love this?" Will asked. "My friend Tyler. Tyler should definitely go with us."

Oliver had never met Tyler, but he didn't see the harm in inviting a friend along. "That sounds fine. Since it's your birthday and all. Do I need to talk Tyler's parents or what?"

Will cocked his head to the side and thought for a moment. "Probably, but just have Mia forward the itinerary and then you can do the parent meet and greet the day of."

Will scribbled down contact info for Tyler's parents and Oliver passed it along, instructing Mia to book two rooms. No way did Oliver want to spend three days in one room with two teenaged boys.

"You're the best, Dad!" William gushed and surprised Oliver with a tight hug.

That probably should have been the first clue.

The day they were scheduled to leave, Oliver and William pulled up to a nice two-story home in a decent neighborhood. As Oliver put the car in park, Will was beyond fidgety, but Oliver wrote it off as excitement. The two of them walked up to the door and Will rang the bell. The heavy oak door swung open and a young girl around Will's age opened it. Her face split in a bright grin when she saw them.

She bit her lip and tucked a lock of her shoulder length, dark brown hair behind her ear. "Hi, Will."

"Hi," William replied far shier than Oliver had ever seen him and he nearly leaned into Oliver which he hadn't done in almost five years.

"Tyler, is that Will?" a voice asked from further back in the house. "I want to talk to his dad before you guys leave."

And in that moment, it became clear to Oliver that he had both over- and under-estimated Will's maturity.

Oliver silently turned to look at Will who was studiously avoiding his glance.

"Mayor Queen! Good to see you. I'm George, Tyler's dad. This is my wife, Marguerite." Tyler's dad, a big bear of a man with a wide, welcoming smile extended his hand in greeting. Oliver reached out to shake hands, working hard to keep the friendly smile on his face. George directed them into the living room and motioned for Oliver to take a seat. He and his wife followed suit while Tyler and Will trailed behind in the foyer.

"We're really glad to finally meet you," Marguerite said as she settled on the sofa. "Will is a good kid, but you can understand our hesitation at sending our daughter on an overnight trip with a boy, even if you're going to be traveling with them."

"Absolutely." Oliver nodded. "I'll be frank with you. I—uh— I didn't actually know Tyler was a girl. If you're uncomfortable with her going with us, I totally understand and William will have to get over it, particularly since he could have avoided this by being completely honest with me."

The last part was said in a louder voice directed towards Will who had the good grace to duck his head and turn away.

In a lower voice, he continued. "William doesn't know it yet, but my assistant, Mia, will be traveling with us." Or at least she would be once Oliver called her and bribed her with double overtime and a luxurious hotel room. "Tyler can room with her so that there's an adult with her overnight. Will's bunking in my room."

Marguerite smiled brightly and letting out a relieved sigh. "Oh! Well, then that does make this a lot easier. Thank you so much! This is a wonderful opportunity for them both."

Oliver wrote down both his and Mia's contact information and handed it to George before shaking hands with both of them again.

Just as they stepped out the door, Tyler remembered she needed to use the bathroom.

Will's eyes bulged in a slight panic as he realized that left him and Oliver alone.

"So what? You thought I just wouldn't notice that she was a girl?" Oliver asked as they walked to the car. "Maybe I'd go oblivious for three days while you roomed with your girlfriend."

"She's not my girlfriend," William muttered, his entire face going beet red.

Oliver stopped and glared at William. "She's a girl. She's your friend. From what I can tell, you like her and she likes you. If it's not official, you're probably hoping this trip would get you there, right?"

William shrugged, refusing to make eye contact.

Oliver sighed. "Will, I know you're at that age where you're starting to want to… physically try new things, but—"

William's gaze shot up at that. "Dad! We've already had this talk!"

"Well, you used me to try to get three days in a hotel room with your girlfriend, so we're having it again!" Oliver barked. "I'm not trying to embarrass you. I'm just telling you to slow down and be careful. You have the rest of your life to be an adult and do… adult things"

William groaned.

"Fine," Oliver relented. "Here's how this is going to go. We're picking up Mia. She's rooming with Tyler. You're rooming with me. You two will never be in a room by yourselves. Got it?"

"That's not fair!"

Oliver laughed, a dry sound that didn't actually convey humor. "That I won't let you spend three nights in a hotel room with a girl you're attracted to? What's unfair about that?"

Will glared at Oliver. "I've googled you, you know. You weren't exactly a choir boy when you were my age."

Oliver mouth snapped closed. "If you've googled me, then you know what a mess I was because my parents let me do whatever I wanted when I was your age. They wouldn't have blinked twice about me having a girl in a room for three days at 15. And I did everything I could trying to figure out where the line was and I never found it. It took nearly dying and five years of fighting for my life every day to straighten me out. I was hoping not to have to take such a drastic route with you."

William opened his mouth to respond but Tyler bounced out of the house and started going full force about how excited she was to be going to Chicago. The two of them climbed into the back and Oliver might as well have disappeared for as much attention Will was paying him, leaving Oliver to steadfastly refuse to think about whether or not William had taken The Big Step or was just hovering around the idea.

Mia was waiting for them outside of her apartment complex, overnight bag in hand. Her eyes sparkled with laughter as she slid into the front passenger seat.

"Well if there was ever any doubt he's my kid," Oliver muttered and then sighed. "What am I going to do with him? He's only half way through high school!"

Mia laughed out loud.

"You're definitely going to have to keep an eye on them." She tossed a glance over her shoulder at the two kids who were absorbed in their own little world. "They're kind of adorable, though. Tyler and William sitting in a tree…"

"So not funny," Oliver groaned.