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Chapter 374: A talk with Maria.

“Oh wow, your face went red in seconds…” Maria said, mostly in surprise rather than out of a desire to tease me. And yeah, not shit I went red.

Though, to be honest, the more I thought about it, the more I accepted it. After all, my first face-to-face encounter with… Diana was at a love hotel, with me as a customer going with five women. That must’ve already made some sort of impression, so her knowing I’d been going to another hotel with the same girls wasn’t as huge as I first thought. It was awkward that Maria, my boss, also knew I was frequenting love hotels, but with five girlfriends, it wasn’t too hard to guess that I probably had an active sex life.

Honestly, yeah, it was better than she knew. Saved me the awkwardness of explaining myself… IF I ever saw her again.

“So I left an impression?” I asked Maria, rubbing the bridge of my nose. “What kind?”

“Hmm… How do I say this?” My boss stroked her chin with over-dramatic gestures. “She’s… interested, but… You see, she’s 26, like me. But unlike me, she’s a lot more conflicted about having feelings for a younger man.”

So the thoughts I felt from her were true? She WAS interested and happy to see me that day. It made me very happy to hear, but…

I grimaced and nodded. “I understand. Who’d be crazy enough to date a guy 8 years younger?”

Maria glared at me as she harshly cleared her throat.

I gave her a small smile. A little revenge for being so amused over my embarrassment. “But she… likes me? Really?”

“Like I said, you made an impression, that’s all.” Maria quickly said, but it felt like she was almost correcting herself. “She’s single and very picky about men. No, wait, not picky! She’s…”

It was at times like these that I wished I could read the minds of people not directly connected to me. It felt like Maria was hiding something. Either her friend wasn’t as interested in me as she first claimed, or…

I chuckled. “You’re trying to hide her real opinion of me, aren’t you?”

Maria flinched. “...Since when did you get good at guessing these things?”

“I spend most of my time with women rather than men,” I said. “I’m starting to understand how it works. If she’s interested in me, you don’t want me to get cocky, right?”

“...Ugh.” Maria sighed and shook her head. “Look, just think you two would really hit it off. I’m actually so confident, that I don’t want to give either of you any… preconceptions. Here’s my proposal. Let’s go on a double date. You, Thomas, Diana and me.”

I felt a strange, awkward chill, and I think my misgivings were clear on my face.

“What? You think it’s a bad idea? Think we’ll get in your way, smooth guy?” Maria asked, pouting and crossing her arms.

“N-No, it’s just… Wouldn’t it be weird?”

“It’s not like I’m proposing we all rent the same room at a hotel! I’m saying we go out, have fun, we help you break the ice. Unless you tell me you can effortlessly carry a conversation by yourself, because Diana is not huge on talking to strangers, either.”

“...” I opened my mouth to argue, but stopped myself before I could say a single word. Yeah, I’d gotten better at talking, sure, but it didn’t change the fact that all the people around me were better at starting and carrying conversations than I was. Even Noelle, shy as she is, still loves to talk about the things she likes. And starting conversations with strangers… and with a woman older than me at that… It felt beyond me.

Back when I started seeing Mila, Grace and Sarah, they did all the heavy lifting in that regard. They talked to me despite not knowing me and they kept at it even when I couldn’t answer. Then, when I started seeing Alice and Noelle, I had already done some growing and had the advantage of sharing a hobby with Noelle and that Alice was already friends with Mila, Grace and Sarah. Things just… worked out. I like to believe I tried my best, and that things wouldn’t have turned out like this if I hadn’t stepped up when it mattered, but I had to admit things worked… despite me being me. It was, and still is, a depressing thought, and one that kept pushing me to do better next time.

I sighed. “And you’ve already talked about this with Thomas?”

Maria nodded. “And Diana, too, of course. I’m a responsible adult, after all.”

“And if things turn out badly, will you fire me?” I asked.

“Maybe. Depending on how bad you hurt my friend.”

I chuckled. “At least you’re honest about it.”

“It’s mostly a joke. I’m the one pushing for it, after all. I really think you two will click, Oliver.”

I had a hunch, too, but I couldn’t just leave it to luck and fate. I wanted my chance to meet this woman again, and Maria was handing it to me on a silver platter. Saying no would be stupid, and I already had explicit permission to act as I saw fit in the event that I did find her.

“Alright, I’m in.”

“Yes!” Maria fist pumped. “Leave it to me. I’ll take care of everything.”

“...If you don’t mind me asking, why are you so excited about this?”

Maria smiled wryly. “Because Diana’s been going through some rough stuff, and I really want her to start having fun again. She’s always been one to put responsibilities and duty before herself, so I know she will continue doing just that unless I butt in. It’s what best friends do.”

My mind went back to Thomas, to his invitation to his birthday party and the countless other times he kept meddling in my affairs.

I smiled. “I suppose it is.”


************

Chapter 375: Intermission - Anxiety and doubts.

It was still early. Three hours too early, but Diana was already panicking. You couldn’t tell from looking at her, though. Her face was calm and stoic as she browsed through her limited collection of shirts and tops. Her chest, however, felt painfully tight and her heart beat rapidly.

She had a date in three hours. Her first date in years. A date with an 18 year old young man she scantily knew.

Diana didn’t know what she would do on the date. It was a double date, with Maria and her own boyfriend, but even so, Diana was lost. She didn’t even know what to wear.

She grabbed two different tops from her closet. Should she go for something modest and mature or something bright and sexy? It was a hard decision for more than one reason. She wanted to make a good impression, after all, but…

Diana pursed her lips and sat on her bed, dropping the tops on the floor as she tightly gripped her knees.

Since her sophomore year of high school and until that point, Diana only had three boyfriends. Two in high school, one in sophomore year of university. None of those relationships lasted longer than a month. She was also never the one to ask the other person out. She was always the one pursued, and… she had a good idea why. She looked towards the full mirror on the wall of her bedroom and glared at herself.

Diana had the type of body most men drooled over. A large bosom, a narrow waist, large hips, a plump behind, long legs, a good-looking face…  It was all Diana had going for her, however. Her generally stoic demeanor and her sudden glares pushed them all away. She knew it was her fault, but it was, and still is, a reflex that’s nearly impossible for her to stop.

“It’s like you fucking hate me,” they’d say.

She didn’t. She never hated anyone. That face, those glares… were her body’s response to intense nerves and anxiety.

Diana never understood what it was to ‘date’. How was she supposed to act around someone who liked her? Nothing ever came natural, and overthinking made her brow furrow, her eyes narrow and chest hurt.

Maria said it herself. Diana didn’t believe in love at first sight, which was the reason she accepted when previous boyfriends, before then mere acquaintances, asked her out on dates. She wanted to know them and for them to know her, but fear of being disliked led to awkward interactions, and thus to truly being disliked. That the exact same pattern repeated three times drove into Diana the idea, the belief that she was just unlikable.

If Maria hadn’t been there all those years to continuously fight off that belief, it was likely that Diana would’ve fallen into a deep depression.

This time, however, it was different. Diana felt… the ‘spark’, love at first sight. Of course, she knew it wasn’t love per se. It was merely attraction, but… an attraction so strong it kept her up at night, rolling around in bed thinking of what it would be like if this young man and her actually clicked.

It was a dumb, welcome distraction from the worry over her father while he was hospitalized, and welcome still after the day of his passing. Idle fantasies to make her smile with a shake of her head after a tiring day. And now… she had a date with the young man, with… Oliver.

He wasn’t going to be what he was in her fantasies. She wasn’t so deluded as to believe he would be. But Maria spoke highly of him, said he’d understand.

This time, it was Diana who wanted to pursue a man. That he was younger complicated things a bit, but it was the first time her heart pushed her towards someone instead of her brain making her stubbornly pursue a goal. She didn’t want to waste this resolve.

Even if it did end up in disappointment.

“...You miss 100% of the shots you don’t take, though. Right dad?”

God, what would he think about this? He was always one to let he make her own decisions, but she couldn’t imagine he’d be very thrilled to know about this.

And that brought her back to her still undecided choice of outfit. Should she lean on her looks with a sexier look, or should she put on something modest and try to make him fall for her personality? It was clear which option had the better chances, but if Maria was so damn sure about all this…

Diana made up her mind. She grabbed her blue jeans, a black T-shirt and her reliable dark green bomber jacket. She tried them all on and decided it was a winner. After all, they weren’t going to some fancy restaurant. According to Maria, it was something very casual.

All that was left was… her choice of underwear.

They… weren’t going to have sex on the first date, were they? Of course not, so there was no need to pick anything fancy.

But what if it happened? If there was one thing she knew about Oliver, it was that… he was a sex machine. Diana’s cheeks burned at the thought, but it was true. At least, a man going a full night with five women had to be, unless they were just playing cards all their time there. And again, if Maria was to be believed…

Ugh, Diana didn’t know what to do. She even found herself glaring again. She didn’t want to seem… desperate, but she’d be lying if she said it wasn’t something she looked forward to. With how good-looking he was, and that lean, muscled body… Dammit, even the fact he was shorter than her was a plus!

Diana went and picked the only set of sheer, black lace underwear she owned. No one needed to know what she was wearing under her clothes, but if things did go down that way, she wouldn’t be caught wearing old, comfortable panties.

Besides, if things truly got to that point, it meant the boy was worth it.


Comments

written_fantasy

Diana is one of those characters I've had in mind for so long before I even started writing her that she's gone through a million changes in my mind before anything was put to page. And then, even as I wrote her chapter, things kept changing as I didn't think some things fit, or made her unlikable. Some new ideas even popped up when I was writing, which is the reason I have such a hard time working with outlines. I had to edit her chapter several times because there was simply too much I wanted to say about her backstory, but I didn't want it to turn into a case of telling you 'here's is how she is' instead of showing you or having it come up in an in-story conversation. I'm honestly not sure how I feel about it now. I hope you all enjoy it.

midnight_texts

Super excited by Diana's introduction. Firstly I think her dynamic with Oliver is going to be really enjoyable but also because of her being similar to him at the start of the story I think will help Oliver contextualize his own growth. Looking forward to the next chapter!