Trixie's Most Difficult Challenge

by MysteriousStranger

First published

After confessing, Trixie Lulamoon takes Sunset Shimmer on a date.

Confessing was the hardest part. Now the rest should be piece of cake. Or at least that's what Trixie thought.
With no experience in dating, will Trixie's first date succeed or will she make her a fool of herself in front of her crush?

This story was written with the help of my brother in arms, Windsor. Thanks, buddy! :twilightsmile:

First Date

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Trixie's P.O.V.

I did it! I can’t believe those love letters actually worked! What am I talking about? Of course they worked! I am, Trixie Lulamoon. My plans are always flawless. It was only natural that Sunset Shimmer would fall victim to my charms. We were still holding hands when we walked out of the school. I squeezed hers with mine. From the side of my eyes, I could notice that she looked at me and smiled. My body heated up. Look straight ahead, Trixie! I put on my best poker face. She must not find out how nervous you really are!

“So… Trixie. Where are you taking me on our date?”

“O-Our date…?” I tried to smile, but I’m sure I failed completely.

“Yes, remember? You asked me out, I said yes. That’s how it usually works.” I glanced at her. She was smiling caringly. That smile… it’s so beautiful…

“I… umm… well…” I cleared my throat. Stupid, stupid Trixie!

Sunset giggled softly. “You don’t have a plan?”

Her voice, her tone… I surrendered to it. I had to say the truth. After a sigh, I spoke again. “I never thought I would get this far… The moment you took my hand… I just couldn’t think straight anymore…”

“Oh?” I could swear that she blushed. She was surprised by my words, but she quickly smiled again. “It’s okay. We’ll go step by step.” Sunset placed her free hand on her chin to think. “Do you like the mall?”

“I can’t say I don’t.” I made a brief eye contact with her. Even if I looked at her for a short period of time, I felt like if my face was bursting in flames.

“We can go there. With the amount of shops and cafes, we might think on something.”

“It’s better than nothing, I guess.” I tried to sound casual.

“Great! Then let’s go!” Sunset grabbed tighter into my hand and started to run. She was close to drag me.

“Sunset Shimmer, hold on a moment!” My date came into a halt shortly after and glanced at me.

“What is it, Trixie?”

“I was the one to ask you out-” I said as I proudly placed a hand on my chest. “So I must be the one taking the lead.” I added as I started to walk on a faster pace, with Sunset behind me.

“It’s not a competition, you know?” My crush smirked. I continued to walk, ignoring what she just said. Did Sunset really think that she could take control of the date? As if!


Our first stop was an ice-cream shop, where we both got milkshakes.

“Trixie, you could have allowed me to pay.” Sunset commented, as we walked out the shop.

“I was the one to ask you out, Sunset. I must pay for your treats.” I said as I started to drink from my milkshake.

“It’s not a rule, Trixie. We can share the expenses. What if I suggested a high category restaurant for our first date?”

“But you didn’t. Plus, you don’t seem the kind who would go to such place on a first date.”

“No, but my point is, you don’t have to take the lead. We can enjoy ourselves and buy each other treats and gifts.” I huffed and looked away from her, drinking from my milkshake until Sunset spoke again. “You… have never been in a date, haven’t you?” I choked with my drink and started to cough. “My gosh, Trixie!”

“I’m fine! I’m fine!” I managed to say when my coughing started to stop.

“I’m sorry. I didn’t mean to-”

“It’s okay.” After interrupting Sunset, I looked at her. “Yes, you might be surprised that someone as amazing as Trixie has never had a date.”

“I won’t lie, I’m a bit surprised. I mean, you’re beautiful and full of self-confidence.”

My cheeks felt warm after hearing Sunset’s compliments. “Well, apparently not everyone thinks that. Most people find me annoying. I’m sure you do too.”

Sunset smiled warmly at me. “I would be lying if I told you I didn’t find you annoying, but I saw all the effort you put in confessing your feelings to me. I saw how much you struggled to say how you felt. No one can fake that. I know that what you feel is real.”

“Oh…” I could barely keep eye contact with Sunset. “O-Of course I’m being serious about my crush on you!” I inhaled and exhaled loudly before speaking again. I was anxious about my next question. “I-Is that why you accepted to go out with me? Because of my honesty?”

“Partly, yes.” Sunset didn’t lose her smile. “Also because back in my home world, I was so focused on my studies that I didn’t bother to have friends. I also rejected many date invitations. When I first came here, it was the same story. I only dated someone to be popular; but after my change of heart, I decided to be more open about invitations. You were the first person to ask me out after my redemption.” She placed an hand on my shoulder after saying the last. I had to repress a gasp. “And so far, I have no regrets. I’m having a good time, Trixie. You’re not as bad as I thought.”

“I-I…” For some reason, I couldn’t form any kind of word. My tongue was betraying me! I shook my head and closed my eyes, regaining my confidence. “O-Of course you are! You’re with the great and powerful Trixie! Was there ever any doubt?”

Sunset giggled and finished her milkshake before throwing the empty cup in a trash can. Then, she proceeded to take my hand before sighing happily. “Yes, I’m definitely having a good time. How about you, Trixie?”

“W-Well, umm…” I cleared my throat. I think my body has never been this hot! “T-Trixie’s having a good time as well. And she’s pleased to hear that so are you.” I finished my milkshake and threw the cup away in a trash can.

We walked in silence for a little while. Honestly, I didn’t mind. I could fully enjoy our hands holding tightly together. However, the moment ended when she pointed to a nearby store. “Can we go to that clothing shop? I need to buy something.”

“Okay…” My reply had signs of disappointment. I didn’t want our moment to end so abruptly.

“Come on, Trixie! You can buy something as well if you want to.” Sunset practically dragged me to the clothing shop.

“Slow down, Sunset! We’re literally a few steps away!” Sunset didn’t reply. She went straight to the pants area.

“Let me see. I ripped one of my jeans in the leg area a few days ago. I need to replace it.”

“Why didn’t you come earlier?”

“I had plans with my friends. I was busy.”

“Hmm, you have an active life don’t you?”

“More or less.” Sunset smiled at me. My cheeks burnt again, but I managed to keep eye contact. “Sometimes the seven of us hangout, other times I only meet up with one or two of them, but there’s also days where I stay at home with Ray, reading, or just playing videogames.”

“R-Ray…?” My heart sank a little by the mention of that name. Do I have competition?

“My leopard gecko. He’s my pet.”

“Oh, okay, cool.” I looked away, embarrassed, and Sunset chuckled.

“Trixie, if I was already seeing someone, I would have told you.” She noticed my sad tone when I thought Ray was a person.

“Really?” I looked at her again. She nodded.

“Of course. I’m not the kind of person who dates multiple people at once. Besides, didn’t I just tell you that you were the first person to ask me out in a while?”

“Well, Trixie obviously forgot. She heard a third party and she got worried.”

“Aww, Trixie…” Sunset patted me on my head. I frowned at her, but I’m sure she could see my blush, especially since she was smiling warmly. “You’re so cute.” I huffed, crossed my arms and avoided her gaze. I’m not used to be called cute, but for Sunset… I’ll make an exception. “Say, Trixie, why don’t you try out some clothes as well?”

I dared to look at her into her eyes. Forcing myself to not smile wasn’t easy. “Okay, fine! I’ll do it, just so you stop looking at me like that.” Sunset giggled and walked towards the torso wear rack. I stayed to first take a look at the jeans. I didn’t see anything I liked, so I moved to the torso section just as Sunset headed to the changing room. I browsed until I eventually found something I liked. A sleeveless sweater. I took it and went to the next free changing room I could find. Luckily, it was of my size. I didn’t look bad at all. After walking out the changing room, I went straight to the cashier. “I’m taking this. Can I keep it on or should I change back?”

“You can keep it on, miss. It’s no problem.” The shop attendant said before I paid. “Let me give you a bag so you can place your previous clothing in it.”

“Thank you.” I walked towards the bench which was next to the changing room Sunset was in. and sat on it “Take your time, Sunset! I’ll be right here.”

“Okay! Did you buy something for yourself?”

“I sure did!”

“Great! What did you get?”

“You’ll have to come out from there to find out. I’m not telling.”

“Alright, give me a couple of minutes.”

“Trixie will be counting them! If by the time I reach 120 seconds you’re not out, I’m leaving!”

“Oh, come on, Trixie, you’re not going to put me on a timer for real, right?”

“115 seconds remaining!” Sunset didn’t say anything else, but I could hear she was hurrying up to get dressed. I covered my mouth to mute my malicious chuckle. I was, of course, not planning to abandon my crush in the middle of our date, but I would hide should the timer reach zero.

However, it wasn’t necessary. When I reached a minute and a half, Sunset walked out the changing room, wearing a pair of light blue jeans and a white tank top. Oh, my… this girl will be my doom. She looks absolutely astonishing! While she checked herself I the mirror, I focused my eyes straight ahead, trying not to be so obvious with my blush. “Hmm… I don’t know. These jeans don’t look appealing to me. What do you think, Trixie?” I heard her call me, but I was unable to form any kind of words. “Trixie?” Sunset turned around and walked towards me. She then bowed in order to make eye contact with me. “Are you there? Hello!” Sunset snapped her fingers in front of me, which waked me from my trance. I shook my head and met face to face with her. “Good, you’re alive!”

“I’m sorry, did you say something?” Being only some inches apart, there was no way I would be able to hide my flush.

Sunset sighed and stood straight before me. “I was asking you how I look.” She said before slowly spinning around. “So?”

“Y-You look…” I coughed. “You look… fine.”

“Really? You think so?” I nodded. “Come on, Trixie, you can’t be serious. I look… simple. Too simple.”

“I-I think you look p-p-p… pretty…” I closed my eyes after managing to say the last. I didn’t want to know how Sunset reacted. I could notice that she didn’t move. Slowly, my curiosity won me over and I dared to open my eyes to look at Sunset. She had a hand on her mouth and she was… blushing?

“Pretty? Is that how you think I look?”

“No…” I said before standing up to gaze at her straight into her eyes. “I don’t just think you’re pretty, I’m certain that you are.” Finally, I was getting the confidence to say what I wanted. For the first time, Sunset was at a loss of words. Her cheeks were turning bright red. She didn’t move her hand from her mouth and her eyes were… wet?

“Trixie…” My date finally managed to form words after several moments. “I… I…”

“Excuse me, ladies…” the shop attendant approached to us. We both turned our heads to look at him. “Other customers wish to use the changing room you’re blocking. Would you please…?”

“Oh, oh! Yes, of course!” Sunset chuckled nervously. “I’m sorry. I’ll try a different attire in another changing room.” She dashed into the changing room she was just in to take her clothes before heading back to the racks with clothes. She didn’t glance at me a single time during her rush. Was she avoiding me?


We left the clothing shop after Sunset found an outfit she felt comfortable with. In the end, she bought similar jeans to the ones she had ripped off. I was holding the bag containing my previous jacket. I glanced at Sunset. She didn’t say anything to me since she started to avoid me. I’m sure it’s because I made her cry. Just great. Nicely done, Trixie…

When it was clear Sunset wasn’t going to say anything, I decided to speak. “S-Sunset…”

“Hmm?” She glanced at me. Her face didn’t show happiness, nor sorrow.

“Listen, I-I’m very sorry for upsetting you. It really wasn’t my intention. Please, forgive me…”

“Upsetting me?” My date raised an eyebrow in confusion.

“I made you cry. I didn’t mean to do that…”

Sunset chucked and smiled. Now it was my turn to raise an eyebrow in confusion. “Oh, no, no, Trixie. You got it all wrong. You didn’t offend me in any way.”

“Huh? Then why were you crying? I saw your eyes were wet.”

“Well, about that-” I could notice Sunset’s cheeks turning red. “I got emotional. It has been a long time since someone called me pretty in a meaningful way.”

“Not just pretty. You’re really beautiful, Sunset. So much, that I can barely look at you into your eyes without passing out.”

Sunset’s cheeks became even more red. “Trixie… you’re too kind.”

“Ever since I saw you perform at the Battle of the Bands, your determination, the way you sang… I just couldn’t stop thinking about you. Your smile, your eyes, your hair… you changed my perspective on you. Since that night, I tried to approach you, but I feared how would you react. Only unkind words came to my mouth. Then I realized I could express what I truly felt with words. I wasn’t sure if the love letters would work, but it was the only way to make my feelings reach you.”

“Oh, stop it, Trixie!” Sunset covered her face with a hand and looked away. “If you keep going, you’ll run out of things to say on our next date.”

“N-Next date?” I blushed as hard as Sunset. “There will be more?”

“Absolutely.” She smiled at me. I didn’t care that she saw me blushing anymore. “I’m having a great time and I’m starting to like you. I accepted going out with you because I was curious. I wasn’t expecting to actually feel something for you.”

“U-Uh… w-well…” my tongue was betraying me again. I don’t believe it! Sunset actually likes me?! I’m squealing on the inside! Aaaaaah! Alright, Trixie, stay cool. Don’t do anything that blows this up. “O-Of course that you like Trixie! It was the expected. No one can resist Trixie’s charm.”

Sunset chuckled again and took my hand. I gasped and looked at her. Her smile was different now. It looked like the one I make whenever I think of her. Sh-She’s not kidding… “Since we’re here, why don’t we go to the cinema upstairs? There’s a nice movie that will start soon.”

I nodded and opened my mouth, but I was unable to form any words. We didn’t say anything else while we headed to the cinema. While we walked, I think she gazed at me, but she looked in another direction whenever I glanced at her. Oh, Sunset, you’re so busted! I decided not to say anything… for now.

Sunset and I made it to the cinema. I intended to buy the tickets myself, but Sunset stepped in. “Allow me to pay the half, Trixie.”

“It’s okay, Sunset. I got this.”

“Trixie, please, don’t make me argue. I already explained that it’s not necessary that you pay for everything.”

“But…” Sunset placed a hand on mine, successfully paralyzing me.

“No buts. Just let me, okay?” The tone of her voice, the way she looked at me and her touch prevented me from saying anything else. I sighed and placed half the money on the counter. “Thank you.” My date smiled and paid the other half. After buying our tickets, we headed to the waiting area and sat, since the movie wouldn’t start until in a few minutes.

The seat we were sitting in had space for more people, but we were the only ones sitting there at the moment. Sunset left some space between her and me. I placed my arms between my legs and focused my eyes on them.

What should I do? She has pretty much said she feels the same way as me already… should I… take the initiative? I glanced at her. I could only see the back of her head. She had her legs crossed and a hand on one of them. Her other hand was holding her chin. Come on, Trixie, you can do it! You’re not going to make a fool of yourself. Slowly, I started to scoot over the couch until I was right next to her. She didn’t notice how close I was until I placed my head on her shoulder. She gasped and turned her head to me. “I hope you don’t mind if I get… comfortable.” I said, barely being able to keep my cool.

“Of course not.” Sunset smiled at me and leaned her head on mine. “As long as you don’t mind if I get comfortable as well.”

“Trixie has… no objections.” I added before relaxing on her shoulder. See? It worked! Now, time to mess with her a little. “Sunset…?”

“Hmm?” her eyes were closed. She still had a smile on her face and her blush was crystal clear.

“When we were coming here, I noticed that you glanced at me whenever I wasn’t looking.”

“Oh…” Sunset’s eyes shut open and her cheeks became even more red. “Y-You saw that, did you?”

I nodded. “Yes, and Trixie must say that she’s disappointed of you.”

“Disappointed? Why?” Sunset raised an eyebrow in confusion.

“I’m disappointed that you did it while I wasn’t looking. You know how much I enjoy attention.”

My date blinked a few times, then smiled and accommodated her own hair with her hand. “I-I’m sorry. I guess I’m a little nervous.”

“Is that so?” Sunset nodded. I could indeed see her nervousness. “Should Trixie give you more space, then?”

“Don’t you dare, I’m enjoying this.” Sunset laid her head on my shoulder again.

“Very well, I shall grant your wish.” I gazed at my crush. Her eyes were closed. I kept staring at her, only losing eye contact whenever I blinked. Her desire to stay close to me filled my heart with joy. I wanted to squeeze her with a hug, but people started to enter into the cinema. Sunset heard the footsteps and opened her eyes. She sighed sadly.

“I guess our time is over… let’s go.” My date reluctantly stood up. She looked upset, so it was up to me to cheer her up. Upon standing up, I took her hand and squeezed it. She quickly glanced at me. I locked eyes with her and smiled slightly.

“Don’t get the wrong idea. Trixie has her reasons.” I decided to joke with her. Sunset smirked, following my game.

“Oh, don’t worry. I haven’t forgotten that the Great and Powerful Trixie has always her own motives for her actions. What shall I do for you in return?”

“Oh, we shall see. For the moment, until Trixie decides that your debt has been settled, you must remain with her.”

“I unhappily accept your terms.” Sunset couldn’t keep her face straight anymore and burst in laughter, which were contagious and got to me as well. “Alright, Trixie-” my date spoke when our laughter started to die out. “We should probably hurry or we’ll miss the first part of the movie.”

“Are you forgetting about the ads before the movies? We could stick around a little longer.” I stroked the back of her hand with my thumb as I spoke, which got Sunset all nervous.

“As… much as I would enjoy that, we would risk to lose good seats. Come on, Trixie.” I tried to pout at her, which at first seemed to work since her face turned red, but then she closed her eyes and started to walk towards the line. “I’m sorry, maybe another day I’ll surrender to you, but not today.” I had to walk in a fast pace in order to not be dragged. I’ll let you win this time, Sunset Shimmer. Trixie is not done yet!


The movie wasn’t of my taste, but Sunset loved it, and that was enough to me. Plus, I got to be next to her for two hours straight. During that time, I barely let her hand go. I might have not enjoyed the movie like my date did, but I had a first row to her smile and laughter. That alome was worth the price of the ticket.

Having concluded our date, I was now walking Sunset home. I wasn’t looking forward having to say goodbye to her.

“Trixie, I had so much fun! You have surprised me today, although I feel bad for having the wrong idea about you before.” Sunset did not stop smiling ever since we left the cinema, and neither have I. We were carrying our respective bags, and still had our hands intertwined.

“Don’t you worry about that. Trixie is pleased that she spent the day with her crush, and she’s even more pleased to hear that you had a good time.”

“Oh, I did.” My date looked at me. “I can’t wait to tell my friends all about our day.”

“Just make sure to speak highly of me.”

“Of course. You can help me with the details.”

“Maybe.” It would be weird to speak with Sunset’s friends, but I can give it a shot. For Sunset.

Shortly after, we arrived at Sunset’s home. “Home, sweet home!” my date commented.

“This is where you live?” I took a look at the apartment complex she lives in. It looks old.

“Yes, it’s nicer on the inside. I’ll show you my place another time.”

“I… would love that.” Sunset turned around to see me. Our eyes met again. Both of us got lost in the moment.

“This is it… I’ll see you tomorrow at school, right?” Sunset spoke with a soft tone.

“Of course you will. Trixie will be there to greet you.”

“It’s funny. Today I went to school avoiding meeting with you. Tomorrow, I’ll be looking for it.”

I chuckled. “I’ll be waiting for you by my locker so you don’t have to search for me.”

“Thank you.” We remained gazing into each other’s eyes in silence for several moments. I would admire them all day.

“So…” I decided to break the silence. “Are we… official? Are you my… girlfriend…?” It was hard to tell which blush was brighter. Hers or mine.

“Isn’t it obvious, Trixie?” Sunset leaned her head closer to mine.

“I-I need to hear it from you. Otherwise I won’t fully believe it…”

“Oh, really?” Sunset smirked. “Hmm, I don’t know. I might need more time to decide. Keep my mind open.”

“If that’s the case, then I might try going out with someone else. Maybe I could ask one of your friends out-”

“Okay, you win!” Sunset raised her voice all of the sudden. “Yes, we’re dating. You’re my girlfriend. Happy?”

This was fun. I didn’t take Sunset for the jealous type. The idea of me dating someone else did not cause her amusement at all. That made me even more happy. “Not quite. Let’s leave one thing clear here.” Sunset raised an eyebrow. “You, Sunset Shimmer, are Trixie’s girlfriend. Not the other way around. Got it?”

Sunset fluttered her eyelids before chuckling. “I got it.” She hugged me afterwards.

“Wh-What are you doing?”

“Giving you a goodbye hug?” Sunset released me from the hug. “What’s wrong about it?”

“What’s wrong is that you’re trying to steal Trixie’s prominence from her date. I must be the one who has the last word.”

“Trixie, I thought I told you this was our date. There’s no need to-” her words were silenced when her lips met mine. She even dropped the bag with her new clothes because of the surprise. The peck was brief. I pulled away merely a second later. Sunset didn’t move a muscle.

“Done. I have the last word.” I smirked. My heart accelerated just now.

“Uh-huh…” My girlfriend was spacing out. She’s so beautiful… I took her bag, placed it on her hand and closed it.

“Sunset?” she wasn’t replying. I waved a hand before her face, but there was no reaction. Okay… I might have just broken her. I searched in her pockets until I found her keys. I tested each of them on the door until one of them fit. I opened the door and lead my girlfriend inside. “Please, close the door as soon as you come back from your trance. I-I’ll see you tomorrow.” I placed her keys back in her pocket and walked out, closing the door behind me. After I was at a safe distance, I squealed loudly and jumped in excitement. She’s so into me! I can’t believe that she lost herself after I gave her a peck! I can’t wait to see her again tomorrow!