Olivia’s POV
As we prepared to leave, I turned back toward Maxwell, wondering what he’d planned for himself. "What about you, sir? How will you spend your night?"
He simply waved off with a dismissive gesture. "Don’t worry about . I’ll just hit the club or sothing. Maybe find myself so company. You two just focus on having a good ti."
I nodded, "Right. We’ll... we’ll see you later then."
"Take your ti, Oliver. You don’t have to even return tonight."
I had to stop myself from showing him my middle finger as we turned toward the door. The pure audacity of the man.
The mont we stepped out of the hotel, I felt the cool Chicago evening air hit my face, and I took a deep breath, trying to calm my nerves.
Walking beside Diane, I made sure to maintain a careful distance between us - close enough to seem normal, but far enough that our skin wouldn’t accidentally graze each other. The last thing I needed was for her to notice how smooth my skin was or feel the subtle curves I was desperately trying to hide.
"So," Diane said as we walked down the street, "What do you do for fun?"
I cleared my throat, keeping my voice low. "I... well, work keeps pretty busy. Not much ti for... this sort of thing."
"This sort of thing?" she asked with amusent. "You an spending ti with people? Or do you specifically an spending ti with won?"
My face burned. "Both, I guess."
Diane laughed, "You’re refreshingly honest, Oliver. Most n would pretend to be experienced playboys."
"I’m not most n," I muttered, then imdiately worried that sounded too revealing.
"No," she said thoughtfully, studying my profile as we walked, "you’re definitely not."
We found a small café with outdoor seating and twinkling fairy lights. It was exactly the kind of place I would have chosen myself - as a woman.
"This looks perfect," Diane said.
As we settled into our seats, she leaned forward slightly. "So tell about yourself, Oliver. What do you do when you’re not being Maxwell Wellington’s right-hand man?"
I fumbled with my nu. "I... read. A lot. And I like movies. Quiet evenings at ho, mostly."
"What kind of movies?"
"Um... romantic codies, mostly." The mont the words left my mouth, I realized my mistake. What man admits to loving rom-coms on a first date?
But instead of looking surprised, Diane’s eyes lit up. "Really? What’s your favorite?"
"The Proposal," I said without thinking, then quickly added, "I an... it’s got good... uh... cinematography?"
Diane burst out laughing - not mockingly, but with delight. "Oliver, you don’t have to pretend. I love The Proposal too. Sandra Bullock is fantastic in it."
I stared at her in amazent. "You... you don’t think it’s weird that I like romantic movies?"
"Why would it be weird? Shows you have a romantic heart under all that shyness." She smiled warmly. "I think it’s sweet."
As the evening progressed, I found myself relaxing a bit despite my constant awareness about maintaining my disguise. Diane was... incredible. She was funny, intelligent, and had this way of looking at that made feel like I was interesting.
After dinner, we walked through the park. It was beautiful in the evening light, with couples strolling along the paths and street musicians playing soft jazz.
"Ice cream?" Diane asked, pointing to a vendor cart.
"Sure," I said, pulling out Maxwell’s wallet from my back pocket. "What flavor do you want?"
"Surprise ," she said with a mischievous smile.
I ordered her strawberry and got vanilla for myself.
As we continued walking while eating our ice cream, Diane kept asking questions.
"Do you have any siblings, Oliver?"
"No," I said simply. "I’m an only child."
"That explains the quiet, thoughtful nature," she mused. "What about your girlfriend? The one Maxwell ntioned at the conference. Tell about her."
My heart skipped a beat. I had hoped this topic wouldn’t co up, but then, Diane is a woman. It’s normal that she’d want to know. "Yes, I... I do have a girlfriend. Her na is Kira."
Diane’s eyebrows rose with interest. "What’s the story there? Why does Maxwell think she isn’t good for you?"
Saying the truth wouldn’t hurt, I guess. Maxwell had already shared that story with everyone. "It’s because... well, she jumped on him once. Physically. To defend when he said so pretty an things to ."
Diane stopped walking and stared at for a mont, then burst out laughing. "She jumped on Maxwell Wellington? Your girlfriend actually physically attacked your boss?"
"She was defending ," I said quickly, my cheeks burning. "He was being... well, he was being Maxwell. Really harsh, and she couldn’t stand watching him tear down like that."
"That’s..." Diane wiped tears from her eyes, still chuckling. "That’s actually kind of amazing. I hope she doesn’t jump on too for taking you out tonight."
I found myself smiling, "She’s... she’s actually pretty understanding. But I really love her, Diane. I wouldn’t want to do anything to hurt her."
Diane’s laughter faded into a more thoughtful expression. "You really do love her. I can hear it in your voice when you talk about her."
"I do," I said softly, and it was the most honest thing I’d said all evening. "More than anything."
"That’s sweet," Diane said flatly, but there was sothing in her tone. Sothing that sounded like a challenge, maybe. "But she’s not here right now, is she?"
I refused to read aning into her words as I turned and continued walking.
We found a street food vendor selling gourt grilled cheese sandwiches, and despite having just eaten dinner, we couldn’t resist. As we shared the sandwich, Diane kept watching .
"You know," she said, taking a bite, "most n would have lied about having a girlfriend. Or at least downplayed the relationship."
I looked at her suspiciously. "Why would I do that?"
"To keep their options open," she said with a shrug. "But you... you light up when you talk about her. It’s actually quite attractive."
"Attractive?"
"Loyalty is sexy, Oliver. The way you defend her, the way your whole face changes when you ntion her... it makes want to know what kind of woman could inspire such devotion."
I didn’t know what to say to that, so I focused on eating, trying to ignore the way she was looking at .
"But you know what else I think?" she continued.
"What?" I asked warily.
"I think you’re curious about what it would be like to be with soone else. Just a little." Her voice was soft, almost hypnotic. "I think that’s why you agreed to this dinner, why you’re here with instead of speaking to your girlfriend on the phone all night."
"I’m here because Maxwell made co," I corrected.
"Are you?" She smiled knowingly. "Because you seem to be enjoying yourself."
I looked away. Praying that this night would just end already so I could go back to the hotel. At this point, sharing a room with Maxwell seed less terrifying than this.
We ended up on a bench overlooking the lake, the city lights reflecting on the water like scattered diamonds. Diane had sohow managed to sit closer to , close enough that I could feel the warmth radiating from her skin.
"Can I ask you sothing?" she said, turning to face fully.
"Sure," I said, trying to sound steady.
"What are you so afraid of?"
The question caught off guard. "What do you an?"
"You’ve been tense all evening, like you’re waiting for sothing terrible to happen. You keep your distance, and every ti I get close to you, you practically avoid ." She tilted her head. "What are you running from, Oliver?"
My mouth went dry. "I’m not running from anything."
"What is it, Oliver? Aren’t I attractive enough? Tell ." she asked softly.
But before I could respond, before I could even process what she ant, she leaned in and pressed her lips to mine.
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