Somewhere in my files, there’s an Excel spreadsheet from 2010 full of terrible financial-themed pickup lines.
Fifteen years ago, when social media was still figuring itself out, I worked with a team on a Valentine’s Day engagement experiment: sharing cheesy finance pickup lines on Twitter.
Digital ad to go to the very manual process of receiving an Investing Pickup Line from Feb. 2010
We built a small site, got modest traction, and moved on. The team disbanded, the site came down, and the project became a footnote — except I never deleted that spreadsheet.
Fast forward to 2025, and I decided to see what would happen if I fed fifteen years of aged, artisanal cringe into a GPT.
Teaching a machine to flirt badly
Using OpenAI, I built a custom GPT trained on that old CSV of pickup lines. The early results were… instructive. The model could parrot back the originals fine, but its original attempts either fell flat or veered into territory that was more uncomfortable than funny. The goal was confident and cringe, not creepy — a line you’d groan at, not report.
Several rounds of fine-tuning later, I found the sweet spot: maximum cheese, zero sleaze. Lines like
“The market clearly hasn’t priced in how fine you are”
and
“Are you an interest rate cut? Because you just made borrowing your attention way too easy.”
Exactly the caliber of terrible I was going for.
Finding the face
The lines needed a character, and a human face was the wrong call. Realistic designs landed too close to “that guy” — the one at the networking event who thinks he’s charming. You know him. You’ve avoided him.
So I turned to DALL·E and started exploring financial animal metaphors. Bears were either too cuddly or too threatening. The first bull attempt — let’s call him Billy Bull — came out endearingly shy and hopeful, the kind of character you’d root for even as he fumbled through a terrible line.
“Billy Bull,” was so endearingly hopeful that you couldn’t help but root for him.
But shy wasn’t the vibe. I pushed DALL·E toward unearned confidence and maximum bravado, and out came Chad Cattle: a buff, self-assured cartoon bull who delivers every line like he just rang the opening bell on Wall Street. Moving from human likenesses to a cartoonishly overconfident animal transformed the whole project from awkward to genuinely fun.
Chad Cattle — a buff, overconfident cartoon bull perfect for delivering these cringey lines.
Shipping it
I mocked up the layout in Figma, built it as a lightweight single-page site, and connected it to the OpenAI API so the lines generate dynamically. ChatGPT helped brainstorm the site name; my wallet made the final call — the $7 .me domain beat the $50 .io option, since this project had exactly zero ROI expectations.
The whole build took just over four hours and cost $17 in new money on top of subscriptions I already had. More importantly, it shipped in time for Valentine’s Day — because when else would you launch a financial pickup line generator?
Come visit:
Disclaimer: All thoughts are my own and not my employer’s. While my employer may provide financial advice, they are not in the business of financially themed romantic pickup-line advice. Nor is anyone, as far as I know. If you’d like to be in that business, reach out and let’s talk. Any likeness of images on the site to people in your real life is unfortunate but coincidental. With assists from AI, all design and development was lovingly hand-crafted by Greg Robleto. Happy Valentine’s Day.