Setting: Path

Barry: *THUD!*

Hey! It's you, Y/N! Fancy running into you here! There's something on my mind that I'd like to talk to you about.

Y'know... I've been feeling really down lately about always losing to Dawn.

It seems like every time we cross paths, she always beats me despite my having a starter with a type advantage against hers...

And I just not training my Pokémon well enough?

Hey! I've got an idea! Let's have a battle, Y/N! I'm sure I can learn a lot from your battle style that way.

I know! Let's make this more exciting!

The loser has to tell the winner their secret, okay? C'mon, let's get the battle started already!

(The two battled, and Y/N ends up defeating Barry's Pokémon.)

Awww... I lost. I guess I have to tell you my secret, then.

My secret is that... I have a little crush on Dawn. However, I can't seem to find a way to get her attention.

I've been pretending to bump into her by accident numerous times, but it doesn't seem to work.

Hm? Did I just see a strange look on your face? Must be my imagination...

Do you have any suggestions on what I should do? I mean, I don't really know what girls think about...

[Choice selection]

⁃ How about making her a card?

⁃ How about making her some Poffins?

Barry: Oh no, I'm not good at that sort of stuff...

Do you have any other ideas? Wait, I know! I'll find the most beautiful flower I can in the park and give it to her!

Come on, Y/N! Hurry up and follow behind me, or I'll leave you behind!

Setting: Park

(Y/N and Barry look around for a beautiful flower in the park.)

Barry: Hey! This one looks pretty. It's even the in same shade as the pink on her dress!

...Umm, Y/N. How should I go about giving this to her? Since you're a girl, I'd figure you'd know how girls like it...

[Choice selection]

⁃ You can practice on me!

⁃ Why don't you practice on me?

Barry: That's a great idea! Hmm... how should I do it? Is... this alright?

(Barry suddenly jumps out at Y/N and swings an arm around her shoulder.)

Barry: Yo, what's up, Dawn? Isn't it a beautiful day today? Look what I got you: a flower that matches that cute pink dress you're wearing!

...Heh, maybe that was too much. Let's try that again.

Hey there, Dawn! I got you this pretty flower. I think it's perfect for a cute girl like yourself!

[Choice selection]

⁃ Thank you!

Barry: Yay! I'm so glad you like it!

⁃ What's with you all of a sudden?

Barry: Huh? You were supposed to pretend to be Dawn... oh, right! That's what Dawn might say after all...

Barry: ...Umm, so what do I say after that? Argh, I'm so bad at this.

You played your part really well, though! I could've sworn I saw your face flush red for a moment there, when I swung my arm around your shoulder.

Hey! I know! I'm going to go back and think of an even better way to approach her with the flower!

You'd better help me think of a way, too! See you here tomorrow at the same time! And don't be late, or I'm fining you ten million!

(Barry immediately scurries out of the park, leaving Y/N behind.)