The Madness Of Approaching Women.

A green lambo truck was parked beside a park, attracting many envious stares like a magnet.

Inside this lambo truck, an handsome specimen sat beside a sorry shrimp. 

The handsome specimen was busy with something on his phone, yet he still managed to come out looking like he was posing for a photoshoot.

The sorry shrimp on the other hand, looked even sorrier and shrimper than ever.

Hugo decided that here was the place to finally make a bold move. 

Parks were filled with people looking to relax and unwind, afterall.

He spotted a girl jogging on the track, her ponytail swinging in rhythm with her strides. Seeing her dazzling long legs and gorgeous figure, Hugo was moved. He decided to start with her.

Trying to psych himself up, he muttered, "Alright, Hugo. You've got this. Just a simple, encouraging comment. How hard could it be?"

He stepped out of the car and jogged up beside her, already out of breath after two steps, and managed to wheeze out, "Keep going! You're almost there! Unless you're just trying to outrun your problems."

The girl slowed down, casting him a puzzled look as if she wasn't sure whether to laugh or call for help. "What did you just say?"

Realising his mistake, Hugo quickly backpedaled—figuratively, because literally, he was already gasping for air. "I-I mean, uh, running's great, right? Keeps the heart healthy and, um, your problems far behind…?"

She raised an eyebrow. "Are you saying I look like someone with a lot of problems?"

"N-No! No, of course not!" Hugo stammered, his face flushing as red as his briefs. 

"You just, uh, seem really focused, like you're running from something… or to something… or maybe for something? Or just… running?"

The girl stopped completely now, hands on her hips, staring at him like he was some kind of strange new species. 

"You know, I was just running to exercise, but now you've got me wondering if I should be running away from this conversation."

Hugo, realising he'd run himself straight into a verbal ditch, decided it was time to abort mission. "Uh, yeah, well, I'll just… let you get back to it. You're doing great, by the way! Really… problem-free!"

As he stumbled away, she called after him, "Maybe you should try running more yourself. From awkwardness!"

Hugo groaned, but when he saw that the challenge tab had increased by one count, he gritted his teeth and grew resolute.

Although the system had not stated the punishment for failure, Hugo didn't dare to fail this challenge. 

What if it was something as sinister as the eradication of one of his testicles?

Or unshavable pubic hair?

Hugo hurriedly scanned for another target. He glanced at Sanchez in the lambo truck and found him to be reeling with laughter.

Hugo scowled. Did he think this was funny?! Something was on the line here!

Something unknown but guaranteed to be deadly!

As he was still lamenting inwardly, he spotted a girl walking an adorable fluffy dog. 'Dogs are always a good conversation starter', he thought. This'll be easy.

He waddled over, putting on his best 'friendly guy' face. "That's a cute dog! Bet it's as stubborn as its owner, though, right?"

Sanchez had said to compliment her sporadically. This should be sporadic enough, right?

The girl froze, her hand tightening on the leash. "Excuse me?"

Hugo blinked, realising he'd somehow stepped in it—figuratively, thankfully, though he was starting to wonder if he was about to be dragged into something literal. 

"I mean, not stubborn in a bad way! Like, in a good way! You know, strong-willed? Independent?"

The girl glared at him, her eyes narrowing as if she was debating whether to let the dog off the leash to attack. "So, you're saying my dog and I are difficult to deal with?"

'Damn you!'

How do these girls think?! Why must they always misinterpret his words?!

"No, no, not at all!" Hugo stammered, "Just that, you know, stubbornness can be a sign of… character! Like, you both know what you want, and you're not afraid to go after it! Which is admirable!"

The dog barked, perhaps sensing its owner's irritation, and the girl took a step closer, her voice dropping to a warning tone. "I don't think we need your admiration. Or your insults."

Hugo held up his hands defensively. The growl of the dog was even deeper than his new bike's! 

He hurriedly tried to protect his ankles...

"No insults! Just, uh, compliments! You and your dog seem like a great team! Like, a dynamic duo! Batman and Robin, but, uh, with fur and—"

Before he could dig himself any deeper, the girl yanked on the leash and started walking away, the dog following obediently. 

"Next time, try not to compare a woman to a dog," she called over her shoulder, leaving Hugo standing there, feeling like he'd just been chewed up and spit out.

After staring at nothing in particular for some minutes, Hugo finally snapped out of his daze. He gazed around listlessly and sat on a bench.

His life seemed really bleak at the moment...

"Chill out bro, that's the 'I want to find a cliff' look." 

Unknowingly, Sanchez had arrived by his side and gave him a pat on the shoulder. 

"Is it always this difficult?" Hugo's voice came out almost like a whisper.

"It is, and until you reach a certain level, it still would be. But to reach that level where you can say anything and it would work, you need to be tempered."

"Are you at that level?"

Hearing this, Sanchez pulled a wide grin and leaned back, flaunting his cultivation level to the newest member of the sect.

"Of course... I'm at the legendary pickup line stage. This means I can safely use pickup lines without it backfiring. This is your goal."

Hugo clenched his fist and a look of determination appeared in his face. 

This was his goal. It was do or die!

He had to do this!

_____

5 minutes later...

The girl tilted her head, clearly unimpressed. "So, you lift books to get stronger? Is that your workout routine?"

"Well, I—no, I mean, yes, sort of?" Hugo fumbled, realising he was only digging himself deeper. "But I mostly read them! For the knowledge! And, uh, sometimes to impress girls… not that I'm trying to impress you! Unless it's working, in which case… I am?"

She stood up, gathering her things, her patience clearly worn thin. "You know what? I think I'll take my weird ideas and leave you to your… bicep curls. Good luck with that."

_____

6 minutes later...

The girl crossed her arms, staring at him like he was a particularly annoying pop-up ad. "So you're saying I have a coffee addiction and unresolved life issues?"

Hugo's mind raced as he tried to backpedal. "No! No, not at all! I just—well, maybe you just… really enjoy coffee? Which is totally fine! Because coffee's great! I love coffee! We love coffee together! I mean, it's not weird to say that, right?"

She sighed, turning back to her phone. "Yeah, I'm going to just pretend this conversation didn't happen."

_____

7 minutes later...

"I was just trying to be funny!" he protested, but she wasn't having it.

"Funny? More like cringeworthy! Do you even realize how insulting that is? Next time, maybe try saying something nice instead of making me sound like a reject from a bad kids' show!"

Hugo's face went pale, and he fumbled for words. "I—uh, I didn't mean it like that! I thought you'd think it was cute!"

"Cute? Right. Because being compared to a cartoon cat is every girl's dream. Thanks for that!" She stood up, eyes blazing. "Enjoy your day, 'Mole-Cat.'"

As she stormed off, Hugo sat there, mouth agape, his mind racing. He watched her go, utterly mortified. "Wait! I can explain!" he shouted after her, but she didn't look back.

Hugo sighed and wiped his sweaty forehead. His eyes were watery and bloodshot, making him appear like a desperate virgin...

Hugo realized at that moment that there was one thing Sanchez had said wrong during his lesson...

'What art of approaching women, this is madness!'