When Dating Advice Doesn't Work...

by ThePinkedWonder


Chapter 4: Starlight Glimmer's and Trixie's Advice

Well, over the previous six days, I had a whopping seven busts at asking out my new crush, Diane Heart, which was just absu-- I mean, silly! After Spike's, Twilight's, Rainbow Dash's, Fluttershy's, Rarity's, and Pinkie Pie's ideas all failed, and how the last bust ended with one of Diane's eyes hurt, I was done!

Back at Twilight's castle, with my head down as I was walking up to its yellow double-doors, a voice called out, "Buggie? Is something wrong?"

I raised my head and turned around to a purplish pink Unicorn. She was my favorite Unicorn, Starlight Glimmer, trotting to me with a frown of concern on her face.

"Hey, Starie, am I glad to see you! I need some cheering up."

"You do? What happened?"

I lucked out by Starlight returning to the castle on her own since I wanted to see her anyway. I told her about my epic failures. She nearly giggled about the part where that bird dropped...something on me, but knowing I felt so down prevented her from laughing.

"Ouch. I had no idea you struggled so bad at asking out your crushes."

"Well, that's something new you learned about me. But never mind that: I need my big sis to cheer me up."

"Hmm..."

"What's with the 'hmm'?"

"Well, I was thinking about a way you could--"

My eyes widened, and I shouted, "Oh, no! Buck, buck, no! Don't you even think about helping me ask out Diane, Starlight Glimmer!"

"Uhh...what do I do if I already did?"

"Then you forget about it, and cast a spell on yourself if you have to! I’m not risking another bust!"

"But can’t I at least tell you?"

"Nope! I don't want to be tempted!"

"Well, okay. I won’t tell."

Seeing Starlight frown, I felt a jolt of pain in my heart. In a kinder voice, I said, "Wait, I'm sorry about that, Starie. I didn’t mean to yell at you, but it's just--"

But Starlight smiled and assured, "No, it's okay, and I know you've been through a lot. If you don't want me to tell you, I won't, but I promise I'm not hurt or upset."

"You're sure, big sis?"

"Yep, I'm sure, little bro. But I have an idea on how to cheer you up."

That put a smile on my face! "Now that's an idea I want to hear! What is it?"

"It will be a surprise so I can't tell you, but you’ll get it in a little while."

"Okay, and I can't wait!"

"So you go and ‘chillax’ or something, and I'll find you when it's ready."

Starlight sped off to prepare whatever surprise she cooked up in that head of hers. Though, at the time, I didn't consider her plan being not one of Starlight's ideas, but a Starlight idea.


Three hours later, as I “chillaxed” in my room and lay on my bed, reading a new book Twilight thought I might enjoy, Starlight peeked her head through the door and told me her "surprise" was ready. Ha, my big sis didn't need to say more; I jumped off my bed and followed Starlight to her surprise. But Starlight wouldn't tell me where or what it was, and she only told me to follow her.


Walking through the marketplace in Ponyville, where Spike and I were when we first met Diane, while passing by various ponies either talking to each other or in lines in front of the outside stands, Starlight kept turning her head back to forth and seemed to be looking for something. But she still refused to tell me her "surprise".

"Come on, Starie, can't you just tell me your 'surprise'? Maybe I can help you find it."

"No can do, Buggie. If I tell you, it'll ruin the surprise."

"Maybe, but it won't matter if you can’t find it."

As I kept pestering Starlight to spill it, she suddenly stopped walking. She turned her body halfway to me and picked me up with her magic to pull me in front of where she was facing.

"Uh, before I give you the surprise I promised, did I ever tell you about the first spell I mastered as a filly?"

"Yep. You told me when we flew kites together for the first time. And I know you, Starie: you're stalling."

"Whaaaat? Me? S-Stall? What makes you think I'm stalling?" Starlight asked in a voice tone with mock surprise, and with a smile that only proved she was up to something. And probably with one of her Starlight plans. By now, she should know that she can’t fool me.

"Why else would you ask me something like that out of the blue?"

"Well, I...oh!" Starlight pointed her hoof in the direction behind me. "Oh, look who it is! That’s the ‘Diane’ mare you have a crush on, right?"

I spun my head and spotted Diane walking towards us. "Uh, yeah, that's her, but--"

Starlight didn't need to hear any more; she picked me up with her magic, and took us both to Diane. The eye of Diane's that was hurt was now a black eye, but it didn't seem to be hurting much now, given she was smiling and appeared to be in a good mood.

"Oh, hi! Your name's Diane Heart, right?"

"Yes, it is."

"I knew it! My name’s Starlight Glimmer, and I'm sure you know Eric, right?"

"Oh, yes. I have seen him a lot the last week."

I whispered, "Starie, what are you up to now?"

Before Starlight could whisper something back, Diane said, "Well, it's always nice to see you, Eric, but--"

"Yeah, he's a good guy, isn't he?"

Diane looked to her left (Starlight's and my right) and frowned. "Y-Yes, he is, but I need to--"

But as Diane started running to where she was pointing, Starlight teleported in front of her to cut her off. "Hey, did you know he once faced off against Queen Chrysalis to save Princess Twilight Sparkle's life?"

Diane leaned her head to the side and seemed to be trying to focus on something behind Starlight, but Starlight leaned her body to mirror Diane’s head movement.

"I-I heard, and it was wonderful, but--"

"Yeah, and he was so brave, and I was so proud of him. He’s like my little brother, you know."

Still a foot away from both Starlight and Diane, I thought I better make my big sis cut it out. I ran up beside her and started, "Starie, I think Diane's trying to say--"

Before I could finish, Starlight wrapped a foreleg around and pulled me to her. "How awesome a guy you are? Because you are!"

Diane’s eyes widened, and while still trying to look behind Starlight and to someone behind us, yelled, "N-No, wait, I wanted that!"

Both Starlight and I spun around to where Diane tried to get to. Carrying a clear bag filled with berries in her mouth, a brown Earth Pony was walking from a stand that was selling berries. Or was selling berries, because the mare walking away bought the last ten.

"No! I was looking all over for those kinds of berries, and that mare just bought them!"

"Wait, what?"

“You see, Starie? I tried to tell--”

Diane, now with a scowl, looked at me and said, "I know you enjoy talking to me, Eric, but I tried to tell you and Starlight that I needed to get to the stand selling the berries before somepony bought them!"

With Diane mad at me, my stuttering returned. I shook my head hard, struggling to show it wasn’t my fault, and explained, "W-Wait, me? B-But it was S-Starlight that--"

"Please, Eric, I need to go."

With an angry frown, Diane stormed off, and both Starlight and I stared in the direction she ran off in. After Diane was out-of-sight, I glared at Starlight, who wore one of her nervous grins.

"Uh, surprise?"

I’ll give her points for attempting to lighten the mood. Too bad it failed, because it just made me groan and facepalm. "Not funny, Starlight."


Nearing the doors to Twilight’s castle again, I was still ticked off. I was so mad, I refused to listen to Starlight’s apologies that she said, over and over, as she followed me back to the castle. Turns out, Starlight's idea was for her to act as my wingman -- or wingmare -- and talk me up and make me look good to Diane. Obviously, it backfired.

"Oh, come on, Eric! For the thirteenth time, I'm sorryyyyy!"

"And for the thirteenth time, I don't want to heeeeear it, Starlight Glimmer! I told you not to try and help me ask out Diane, but you did anyway, and it backfired!"

"But I just wanted to help you out, like a good big sister!"

"Well, big sis, you did an awful job at ‘helping’ me, because now Diane's mad at me!"

"I know, and I'm so sor--"

As Starlight nearly apologized for the fourteenth time, from behind us, a smug female voice asked, "Wow, you two hardly ever fight. How bad did you mess up, Starlight?"

We spun around to a familiar blue Unicorn, with a smirk, but without her magician get-up.

Yep. "The Great and Powerful Trixie" decided to grace us with her presence. At least, that's how she might put it.

"Hey, Trixie. And yeah, I might've messed up while helping Eric ask out his crush--"

Knowing what I’d be in for if Trixie learned about my screw-ups, I interrupted, "Starlight! Don't tell her!"

But, I was too late, and Trixie’s smug smirk only grew bigger. "Ooh! You have a crush, Eric? Who is she?"

Well, since I realized Starlight said too much, I felt I had no choice but to tell Trixie about my epic failures, or else she wouldn’t leave me alone. You might think that she would laugh her head off, and if you did, I have news for you.

You'd be right. That pony laughed so hard, it “helped” me stop being mad at Starlight.

"Ha ha ha! Oh, oh my stomach! Ha ha ha!"

"Oh, come on, Trixie, cut it out! Eric feels bad enough as it is!"

I sighed and said, "No, Starie, just let her keep rolling on the ground laughing and have her fun. At this point, I won't feel much worse if she just laughs."

A half-minute into it, Trixie calmed down her laughing, mostly, and stood up from rolling on the ground. "Wow, Eric! That, ha ha, was...just wow."

"Now if you're done laughing, I'm going in the castle to forget about these last six days."

"You know, Eric, I can't say I'm surprised that you blew it all those times."

Usually, Trixie doesn’t bother me too much when she picks on me. In fact, I often return her insults, and it becomes friendly banter, which we love doing to each other, though it sometimes annoy Starlight. But this time, it triggered me and I yelled, "Ugh! Come on, Trixie! I let you have your fun, so stop picking on me! I'm not in the mood for it today!"

But Trixie’s smirk quickly flipped into a frown. In a more friendly voice, she said, "No, Eric, I'm not picking on you this time, I promise."

I stopped scowling, and asked, "Okay...so if you weren't insulting me, then what was it?"

"I mean with who you went to for advice, it's no wonder they ended in disasters. And Twilight Sparkle? Really?"

Yep, we are still doing the Twilight Sparkle shaming, and I was wondering if it'd ever stop! I groaned and said, "First, I didn't go to Twilight, and second...what do you mean by ‘it's no wonder they ended in disasters'?"

Starlight chimed in, “Yeah, I don’t get it either.”

"Instead of you going to Diane, you should've done something to impress her so she’d come to you."

A moment of curiosity took over, and I asked, "And even if I wanted to, how would I do that?"

"You do it like me --” Trixie stood on her hind legs and spread her forelegs in boastful fashion “-- The Great and Powerful Trixie!”

With my moment of curiosity over, I said, "Well, Ms. Powerful, even if I were a Unicorn and could do magic shows like you, it wouldn't matter anyway."

"Why you say that?"

"Because whatever you cooked up in that head of yours, I'm not doing!"

Instead of pleading her case, Trixie formed a smirk on her face again, strutted up to me and her purple eyes stared into my brown eyes. "Aw, what's wrong, Eric? You chicken?"

"N-No, I'm not 'chicken'! I'm just sick of blowing it."

Trixie wasn’t having that, so she stepped back, stood on her hind legs again, and flapped her forelegs like chicken wings while clucking like a chicken.

I was not amused and I yelled, "Trixie, stop that! I'm not chicken!"

"What? Bawk! What did you say, chicken?"

Moments away from entering “big sister” mode, or possibly “Overprotective big sister” mode, Starlight ordered, “Okay, seriously, Trixie, leave Eric alone!”

“Yeah, lay off me!”

But Trixie refused to listen and teased, "I can't hear you, chicken. Bawk! What did you say?"

After a couple of seconds, and partly to ensure Starlight doesn’t enter “Overprotective big sister” mode, I sighed and conceded, "Okay, okay, Trixie, you win! I'll do it! What's your idea?"

Trixie stopped her clucking and got off her hind legs to stand on all fours again. "Okay, my next show is tomorrow, and from what you told me Diane Heart looks like, she watches my shows. So how about I let you perform some tricks in it?"

"But how could I impress Diane enough for her to make a move? Even if I do something, you’re the star, so most of the attention would be on you."

"Well, what if I say that I won't be the star this time, but it'll be you?"

Staring at Trixie, I froze in place as my brain struggled to process what came out of her mouth! Starlight wore a blank stare on her face too over it, and we both blinked twice. In fact, after I "unfroze" myself, I thought I should test if this Unicorn in front of me really is Trixie Lulamoon, and I raised my hand in the air and kept it there. This is a special signal Twilight came up with, in case we’ll need to prove we’re us and not an unreformed Changeling or even Queen Chrysalis. All our friends, including Trixie, know about it.

Trixie rolled her eyes and lightly slapped her cheek three times, which means ”it’s really me”. Starlight did as well, and even I did it. The plan demands that everyone do it, even the one giving the signal.

“Oh, very funny, Eric. But look, I know we love picking on each other, but we're still friends, and I'd want to help you if you need it. And right now, you need it."

"Wow, that's...thanks. So what now?"

"First, The Great and Powerful Trixie will teach you some easy tricks that won’t need magic, and tomorrow, you’ll be the opening act of my show."

Starlight asked, "Wait, opening act? But I thought you said Eric would be the star?"

"He is the star...for the opening act."

Of course Trixie meant I’d just be the star of the opening act and not the whole show! But I counted myself lucky that she’d let me star in any part of her shows.

Anyway, for the rest of the day, Trixie taught me some sleight-of-hand tricks, so the fact that I’m not a Unicorn wouldn’t be an issue. As I trained with her, it sunk in more and more that, when Trixie was teasing me by calling me a chicken, she only did it because she really wanted to help me. She's a better friend than I sometimes give her credit for.


The next day, an hour after Princess Luna raised the moon, it was time for Trixie's magic show, with me as the opening act. Trixie hung a huge poster of her face high above the stage and a much smaller one of me beside it. Heh, I’m surprised she did that much for me, with me being “just” the opening act. This was a rare show where Trixie wouldn’t need her “number one assistant” so Starlight was practicing spells with Twilight at the castle.

In fact, it’s not often that I spend time with Trixie without her marefriend Starlight nearby. It felt both odd and refreshing to be alone with her.

As a crowd of ponies gathered in front of the stage, Trixie and I stood behind a blue curtain hung behind the stage. She now wore her magician get-up: a purple hat and cape with yellow and light-blue stars and small circles covering both.

"Okay, Eric, you got pretty good at those tricks I taught you, so you should do all right."

"I hope, but where’s Di--" I started to ask as I took a peek from the curtain at the crowd as I was talking, and when I noticed Diane walking into the crowd, the heartbeats kicked into overdrive. I guess when she got mad at me before, it made the calmness I felt the last times I saw her leave me. Uh-oh.

"Well, I guess you answered your own question, Eric. It’s time to start the show, so get ready."

I stayed put, and Trixie came from behind the curtain and onto the middle of the stage, with the crowd cheering as she appeared. I couldn't see it, but knowing Trixie, she wore her usual smug smile, with her head held high and enjoyed the cheering, because why wouldn’t she?

"Greetings, and welcome to the Trixie Lulamoon Show! I am the Great and Powerful Trixie, but before Trixie amaze you with her grand illusions, first, put your hooves together for Eric Reed!"

Ha, I guess Trixie thought she apologized enough, so she ditched that “The Humble and Penitent Trixie’s Equestrian apology Tour” mouthful of a name. Then again, that still sounds more impressive than "The Trixie Lulamoon Show" if you ask me!

With Trixie giving me my cue, as she trotted off the stage, I came from behind the curtains to the stage to the middle of it, where Ms. Powerful just stood. Looking at the cheering crowd, and then to a smiling Diane near the back, not only did my nerves, which wasn’t a big deal the last few times I tried to ask her out, return in full force, but stage fright forced it further into overdrive!

However, I fought to stay calm, and only one drop of sweat flowed down my face. Not only did I want to impress and win over Diane, but I didn’t want to buck up and ruin Trixie’s show. Both because she’s my friend and because she’s a Unicorn, and is stronger than you might think she is. If I bucked up and ruined her show, Twilight and Starlight weren’t around to stop Trixie from turning me into a pink teacup or something if she got too mad.

"Uh, hey, everybody, uh, I mean, everypony. I *gulp* am The Great and Powerful Eric, and, uh, prepare to be amazed at my multiplying card trick!"

I didn’t plan to call myself “The Great and Powerful Eric” but after hearing Trixie call herself “The Great and Powerful Trixie” so much, it slipped out. Though, as she watched on, Trixie showed no signs of minding it.

One of the tricks Trixie taught me was a card trick to "multiply" a card in my hand. However, my nerves got the better of me. As I did the hand motions and waves, I messed up and revealed the cards I had hidden under my shirt, which I was supposed to grab while skillfully moving my hands and arms to hide my grabbing them. Instead, I made them fall to my feet.

Yep, that got a huge laugh out of the crowd. As I stood with one of the all-time biggest nervous smiles on my face, with my face itself probably looking like a tomato from turning red, Trixie trotted back onto the stage to bail me out -- or just save her show -- by claiming it was "part of the act", which worked! Trixie picked me up with her magic and carried me off the stage and went on to do the "real show".

However, before Trixie trotted back onto the stage, Diane walked off.

Welp, that's nine epic failures.

After the show, which I stayed to watch by peeking behind the curtains in a spot the crowd wouldn't see me, Trixie ran to me. To my relief, she wasn’t scowling or ready to turn me into a teacup, but just had a confused frown on her face. "Okay, what was that, Eric? You did that trick twenty times in a row, so what happened?!"

"'What happened' is that my nerves got the better of me by Diane being here!"

"But you said you were calm the last three times you tried to ask her out, so why weren't you calm this time?"

"Probably because I was on a stage this time!” I growled and facepalmed. “I can't believe I didn't see this coming!"

"Oof. I never met anypony with so much bad luck asking out ponies. Is it a human thing?"

"Nope, it's an Eric Reed thing! But in case you're about to suggest something else, I'm not doing it, no matter how many times you call me a chicken."

In a surprise move to me, Trixie shook her head. "Uh, nope, I wasn't going to suggest anything. You have been through enough."

"Uh...thanks?"

“Besides, I think you tried to ask out the wrong mare. You should ask out Twilight, because you two get along great.”

Wonderful. Even Trixie thought I should ask out Twilight, and I growled louder than I did before. “Like I told Rainbow and Pinkie when they said that, no! But thanks for trying to help.”





Now I’ve had nine busts, which have seriously got to be a world-record!

But, on the next day, there would be one more to have their turn to help me land Diane Heart. And I did not expect to see her!