TMNT Boyfriend Scenarios

The First Date: Leonardo

(Y/N)'s POV

Today was rather slow, but that usually happens when I have something to look forward to after work. Thankfully, I was able to get off a bit early, but I still needed to get ready for my date with Leo tonight. I know he mentioned to wear something comfortable and warm, but that's as much detail as he was willing to give me. I didn't want to look like I rolled out of bed decked out in sweats, so I opted for something between cute and comfortable.

When I got home, I rummaged through my closet until I found a white chunky knit sweater that I thrifted last week and decided to pair it with some faded blue jeans and black combat boots. As a precaution, I also carried a black leather blazer with me as I waited for Leo to arrive.

Usually, I'm not the type to be nervous on first dates, but I just felt different about him. Can I even call this a first date? We'd hung out countless amount of times before, so you'd think I'd treat this like any other day. That one drunken night with him should be what pushes away these nerves, but I still feel all these butterflies in my stomach when I think about tonight. I don't know what it is about him or how he makes me feel this way, but I know it's something I've never felt before.

I was sitting at my vanity, touching up my lip gloss when I heard a light tapping at my window. My heart fluttered when I heard the familiar knocking, smiling as I spun around in my chair and stood up, using everything in me to not sprint to the window to open it in excitement. Unlocking the latch, I lifted the window screen and stepped off to the side to allow Leo in.

I pretended not to notice the vibrant flowers he held in his hand that he desperately tried to hide behind him as he stepped inside.

"Hey." He greeted with a smile, hugging me with one arm as he kept his hand that held the flowers behind his back. As we embraced, I caught a whiff of something reminiscent of the outdoors with a hint of lavender. Is he wearing cologne?

"I got these for you," Leo said as he let me go, bringing the flowers into view and holding them out to me. "I picked them myself."

I blushed, biting my bottom lip as I smiled sheepishly, taking the bouquet into my hands and raising the soft petals up to my nose to smell.

"Thank you. How'd you know I liked daffodils?" I asked, gently placing the flowers onto my nightstand beside me.

He shrugged. "Lucky guess. Are you ready to go?"

"Yeah, where are we going?"

"You'll see."

He held out his hand to me as he stepped towards the window. Accepting his hand, I followed him out onto the fire escape of my apartment and up to the roof. There I was met with a large picnic mat covered in blankets and pillows beneath a large wooden picnic basket and plastic battery-powered candles. There was a small stereo off to the side of mat, playing the slow and romantic sounds of a violin.

"You did this all for me?" I asked astonishingly.

Leo led me closer to the picnic and sat down, beckoning me to follow.

"I figured a girl like you deserved a change of scenery from the city lights. Dinner under the stars instead of a busy restaurant." He opened up the picnic basket sat between us and took out two glasses and a champagne bottle. Popping it open, he poured us both a glass, and we cheered to a lovely dinner.

"If I'd known, I would've dressed nicer." I said after taking a sip from my glass.

He rolled his eyes and smirked. "I think you're shining brighter tonight than the stars above us."

I could feel my face burning, thanking the night sky that masked my beet red face just enough with darkness. Since when did he have such a way with words?

We both ate from a charcuterie board he made with the help of April. I joked and questioned just how much he actually put work into the board without April. He denied ever really needing April's help, and we both laughed and got lost in each other's conversations as the night went on. I don't know how long we had been out on the rooftop, but I didn't care. I didn't want the night to end. Eventually, the basket was empty and so was the bottle. We laid under the blankets on the picnic mat, staring up at the sky in silence. His had his right arm resting underneath his head and his left arm wrapped around me as I rested my head on his plastron and pointed up at the sky at the different constellations I found.

"Do you know what constellations you saw in South America?" I asked.

He was silent for a moment, and for a second I thought he fell asleep on me. "I'm not really sure what their names were, but I know I saw a couple when I'd watch over the village at night. It was really all I could do when I was there."

If I'd known better, I would've paid more attention to the reminiscence present in his tone. He seemed... solemn when he talked about his time in South America.

"What was it like living there?"

Leo sighed. "Aside from occasional gang trying to steal from the village, I'd say it was peaceful. Very different from the city. There I felt like what I did for them matter, even if I didn't get direct appraisal for it. I felt like they really needed me there... like I mattered to them."

I turned my gaze away from the stars and looked up at him, trying to read the expression on his face. He didn't turn to me, assuming he was lost in thought as he stared past the stars.

"Do you miss it?" I asked after a moment's silence.

Leo turned his head and looked back at me, and I could see his expression soften just a bit. "If I hadn't left, I wouldn't be here with you. And I don't regret that at all."

He slowly wrapped his arms around me in a full embrace, pulling me closer to his plastron. There we laid in each other's arms in silence, taking in the night sky and letting our words be swept away with the wind.

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Sooo? What do we think? Is it obvious I'm bored and that's why I'm pumping out these chapters all of a sudden? This one I actually didn't struggle so much to write, considering how long it's been. I haven't figured out what dates I'll be doing with the other three, but I'll figure it out soon enough. I hope you all liked this chapter! Please leave a vote, comment, and share with your friends if you enjoyed it! And I will see you in the next chapter. Bye!