Set some time in between seasons 2 and 3; Spencer and Toby have the conversation about waiting.
I do not own Pretty Little Liars.
It was a night just like any other. A typical rainy Thursday night where Spencer and Toby were sitting on her living room couch enjoying each other's company. Everything was light hearted and easy. He was leaned against the arm of the couch as he held her waist as she leaned her back against his chest. Despite all the other chaos in their lives, they loved these little moments. With coffee mugs nearby and a blanket over them, they had taken up aimlessly asking each other questions. Some they already knew the answers to, others were new that they had never really thought to ask.
"What is your favorite color?" Spencer asked.
"Blue," Toby replied, "What's your favorite movie?" he asked in return.
"Hmm, I'm kind of a sucker for classics," She answered, "What's your favorite hobby?"
"Probably riding and fixing motorcycles. Would you rather see the movie or read the book"
"Usually read the book first. Do you prefer dogs or cats?"
"Dogs. What is your middle name?"
"Jill. Do you like sushi?
"Eh, it's ok. Do you like to cook."
"Yeah, I do. What's your favorite sport?"
"Maybe baseball. I'm not that into sports though. Do you drink?"
"Sometimes. What is your favorite book?"
"Catcher in the Rye. If you could live anywhere in the world, where would you go?"
"Paris. If you could sleep with any celebrity, who would it be?"
He didn't answer right away. Not because he didn't have an answer in mind, but because that question got him thinking about something he had thought about many times before but was always too afraid to ask. He still was, but now was as good of a time as any to finally put it out there.
"Spence, can I ask you something kind of personal?"
"Sure."
"Are you a -" he stopped himself, "Have you ever done that before?"
And that is where the light and carefree mood stopped. She looked at him and squinted her eyes not quite sure where that question came from. "What?" She asked a little taken aback.
Quickly picking up on her reaction, he immediately regretted asking her. "Never mind," he immediately responded, "I'm sorry. You don't have to tell me."
Still looking at him, she thought about it some more. She wasn't offended by the question. In fact, she was almost surprised that they had never talked about this before. They certainly weren't strangers to each other's bodies at this point, but they had never gone all the way yet. It just never felt right. It's not like it was an invalid question either. She had definitely come close a few times, both with him and with some regretful others.
"No," She finally answered, "I haven't."
The usually comfortable silence between them quickly became awkward. He wasn't sure what she would tell him or how she would react. He had secretly hoped that that's what she would say, but no answer would have changed they way he thought about her.
She wasn't expecting him to ask her that question. She was expecting him to say something in response, but was relieved when he didn't. All things considered, it was probably better that they cleared the air about this before they found themselves in a situation they couldn't get out of. But his question got her thinking about one of her own. And hers was a lot more uncomfortable.
"Can I ask you something personal?"
"Of course," he answered in no position to say no.
"Have you ever, you know, besides with.." She couldn't even finish the last part of that sentence. Just knowing about it bothered her too much. But he knew what she meant.
"No," He answered without hesitation, "those were the only times."
He knew that question was coming and he knew he brought it upon himself by asking her in the first place. He wished he could tell her that he was a virgin too. He wished even more that he actually was one and that this was something that they could experience for the first time together.
He was not exactly sure how she found out about his past with Jenna in the first place. He never outwardly told her, but he always knew that she knew. He didn't mind. In fact, in a way he was grateful that he never had to have that conversation with her; that they could talk about it honestly without a lengthy description.
"Would you ever again?" She asked nervously and quietly.
"I would," He answered after thinking about it for a few moments, "as long as I knew for sure that it would be different the next time, I would. It's taken some time, but I've worked through everything. I don't think you can write off anything completely just because of one bad experience." He looked down at her anticipating the reaction on her face hoping that she knew what he meant. That he would never be afraid of taking that next step with her.
She smiled back at him, but there was a look of unease on her face at the same time.
"Would you ever?" He asked her still sensing her discomfort.
A year ago, she wouldn't have been able to answer this question. Having another person seeing her in the most vulnerable way possible was not something she had ever felt she would have been comfortable with. She just didn't trust people easily enough to open herself up to be judged like that. It also didn't help that most, if not all, of her sexual encounters up until that point had been a competition of some sort rather than about love.
Toby was different. She trusted him completely. She wanted to let him in. While with him the idea didn't seem quite as terrifying as it had before, she still wasn't so sure that she was ready to go there just yet. All of her friends had done it already, with experiences well beyond what she wanted to hear about. In one of the few pleasant conversations she could remember having with her sister, Melissa told her that love doesn't have to make sense; that some things just fall into place, but when it's right you know. But why was she so unsure?
"Would I ever? Yeah, sure," She began still uneasily.
"...But..." He continued for her.
"But I'm just not sure I would want to right now. I'm sorry. It's not because of you. Sometimes when I think about it seems like a great idea. Then other times, I think about all of the things that could possibly go wrong and it makes me nervous. Sorry. When we do finally take that step I don't want to have any regrets. I'm sorry, I -"
"Spencer," He interrupted her.
She stopped her rant for a second and looked at him.
"Why are you apologizing?"
"I - I guess I don't want to upset you," She answered meekly.
"Spence, this is the last thing in the world that you should ever be sorry about. If you're not ready, then we'll wait. That's all there is to it. I would never be upset about something like that."
"Really?"
"Of course," He said as he kissed the side of her head, "I want your first time to be perfect. Whenever it is."
She sighed in a disappointed way.
"What is it?" He asked knowing something was still bothering her.
"It's just," She began.
"Just what?"
"You said my first time.."
He looked at her slightly confused, "Yeah?"
"I guess I'm a little bothered by the fact that my first time will never be our first time. I mean it will be our first time together, but not, you know.."
She didn't know how to gracefully finish that sentence. But he still knew exactly what she meant. It was something that he had definitely thought about before but never dwelled on it too much.
"Spencer, I can't change the past. Trust me, I would if I could. But the next best thing we can do is move forward from it. I don't let what happened define me. And I will definitely not let it define us. And like I told you, knowing that it would be different next time would make it a whole new experience."
They were both quiet for a few moments before she finally spoke.
"That actually helped a lot," she whispered much more content than before.
"I'm glad it did," he told her right before the room fell silent again. This time, the silence was back to being the comfortable and familiar silence that it was before this conversation started. Both were relieved that this was all finally out in the open. He knew that she would be ready eventually and she knew that he would wait as long as she wanted. This was the perfect balance.
After what seemed like a while, she finally spoke again, "Would you rather live in the city or the suburbs?"
"City," he answered with a smile, "Do you prefer Summer or Winter?"
"Summer. How many kids would you want to have?"
"Maybe two or three. Do you like flying?"
"It doesn't bother me. Do you prefer the pool or the beach?"
"The beach."
The aimless questioning continued for a little while longer before they both fell asleep in each other's arms.