Chapter 9: Digital Wingman

Chapter 9: Digital WingmanMe:Okay so I’m 16, historically unfuckable, and I need to seduce a girl. Yesterday I got punched by the school quarterback after announcing I have a huge dick (which is true but probably wasn’t my smartest moment). Now I look better somehow—like I actually hit puberty properly—and girls are noticing me for the first time ever. I have exactly zero experience with this and need to complete this "mission" without looking like a complete disaster. Help me not die alone. I hit send and wait for the AI to process what is possibly the most pathetic request in ChatGPT history. ChatGPT:Well, that’s certainly a unique situation. Let me get this straight: you’ve accidentally created buzz around yourself, experienced some kind of confidence boost or physical improvement, and now you need to capitalize on this newfound attention? And you mentioned a "mission" - is this part of some personal goal or challenge you’ve set for yourself? Oh, you sweet, naive artificial intelligence. If only you knew about the floating video game interface that’s currently ruining my life. Me:Let’s just say I have very specific motivation to make this work. Think of it like a quest with actual rewards. And yes, I need to capitalize on this attention before everyone realizes I’m still the same loser who got stuffed in trash cans yesterday. ChatGPT:Alright, I appreciate the honesty - and the gaming metaphor actually helps frame this. Here’s the thing about "seduction" - despite what movies suggest, it’s really just about genuine connection, confidence, and timing. Given your situation, you have some unexpected advantages: 1. The mystery factor - people are curious about you now, 2. The "hidden depths" appeal - smart guy with unexpected confidence,3. The novelty - you’re not the same person they’ve been ignoring But here’s what I’m worried about: if you approach this like a "mission to complete," you’ll come across as manipulative or desperate. Girls can smell that from a mile away. God, even the AI is lecturing me about authenticity. This is like getting life advice from Siri. Me:Look, I appreciate the after-school special wisdom, but I need practical advice. I have maybe a week before this attention dies down and I go back to being invisible. What would actually work with high school girls who are suddenly noticing me? ChatGPT:Fair enough. Here’s some real talk since you want practical advice: Start small. Don’t go for your biggest crush or the most popular girl - that’s too high-stakes and you’ll probably self-sabotage. Pick someone who’s shown genuine interest, someone you can have actual conversations with. Your best move right now? Be the "improved but still approachable" version of yourself. Girls are intrigued by transformation stories, but they’re scared of guys who become completely different people overnight. Specific tactics:- Use your intelligence as an asset, not something to hide- Show confidence without arrogance (easier said than done, I know)- Create opportunities for one-on-one interaction- Actually listen when they talk instead of planning what to say next That’s... actually not terrible advice. But I need specifics. Me:Okay but WHO though? I’ve been thinking about this and I have basically three options: 1. Sofia Delgado - Jack Morrison’s girlfriend, probably one of the hottest girls in school, definitely way out of my league but would be the ultimate power move 2. Lea Martinez - smartest girl in our class, basically married to her textbooks, probably the only person who might actually be intimidated by MY intelligence for once 3. Some random girl of those who’ve been giving me looks today but I don’t really know What’s the strategy here? I lean back in my chair, pretending to take notes while Mrs. Henderson explains something about steam engines. Around me, kids are either actually paying attention (nerds) or scrolling through social media (everyone else). I catch Madison Torres glancing at me from two rows over, which is definitely new behavior. ChatGPT:Oh boy. Okay, let’s analyze these options: Sofia: This is what we call a "high-risk, high-reward" scenario. Dating the quarterback’s girlfriend is either going to make you a legend or get you killed. Given that you already have beef with this Jack guy, this might be playing with fire. But... if you could actually pull this off, the social status boost would be incredible. Just saying. Lea: This is actually your smartest option (pun intended). Intellectual connection is powerful, and if she’s as smart as you say, she’ll appreciate someone who can match her mentally. Plus, if she’s not used to male attention, your newfound confidence might be exactly what breaks through her walls. Random girl: Safest option, least potential for catastrophic failure, but also least potential for major social gains. My recommendation? Start with Lea. Build your confidence there, and if it works, you’ll have proven you can actually do this. If it doesn’t work, you haven’t burned any major bridges. That’s... surprisingly strategic thinking from a computer program. But then the AI continues: ChatGPT:But here’s what I’m really curious about - what exactly happened between yesterday and today that made you "look better somehow"? Because that’s a pretty significant detail for a transformation this dramatic. Shit. I’ve been too honest with my digital therapist. Me:Let’s just say I had a really good night’s sleep and finally figured out how to style my hair properly. ChatGPT:Uh-huh. Right. Well, whatever your secret is, here’s how you approach Lea Martinez: Step 1: Find a legitimate academic reason to interact. Ask for help with something, offer to study together, partner up on a project. Step 2: Show interest in HER thoughts, not just her appearance. Smart girls are used to being valued only for their brains, so if you can appreciate both her intelligence AND see her as a complete person, you’ll stand out. Step 3: Create moments of genuine connection. Share something real about yourself - maybe how it feels to be underestimated, or your actual goals and ambitions. Step 4: Physical escalation should be gradual and natural. Start with casual touches during conversation, see how she responds. And here’s the key: don’t treat this like a video game quest. Treat it like you’re genuinely interested in getting to know an interesting person who happens to be attractive. I glance around the classroom and spot Lea three seats ahead of me, taking notes like she’s transcribing the fucking Constitution. Her hair is in that messy bun, she’s wearing an oversized sweater that makes her look soft and approachable. She’s also the only girl in this class who hasn’t stared at my crotch today, which is either refreshing or concerning. Me:Okay so hypothetically, if I wanted to start a conversation with her after this class, what would be a good opening that doesn’t sound like I’m hitting on her? ChatGPT:Easy. Since you’re both in AP History, comment on the lesson or ask her opinion about something academic. "Hey, what did you think about Henderson’s point about labor unions?" or "Did you understand that part about industrial capitalism? I’m kind of lost." Even if you’re not actually lost, it gives her a chance to explain something, which smart people love doing. Then transition into something more personal: "You always seem to get this stuff so easily. Do you actually enjoy history or are you just naturally good at everything?" It’s a compliment disguised as a question, and it gives her a chance to talk about herself. That’s... actually pretty smooth. For an AI that doesn’t have hormones or the constant fear of rejection. The bell rings, and students start packing up their shit. I watch Lea carefully organizing her notes into color-coded folders because of course she does. Me:Wish me luck. If this goes badly, you’ll probably read about my death in the school newspaper. ChatGPT:Good luck! Remember: confidence, not arrogance. Genuine interest, not manipulation. And if all else fails, just be yourself - apparently the "improved" version of yourself is working pretty well so far. I close the chat and stand up, my heart doing that thing where it tries to escape through my throat. Time to see if artificial intelligence can actually help me complete whatever the hell this system mission is supposed to be. Lea’s still at her desk, writing something in her planner like she’s scheduling world domination. Here goes nothing.