AI Surprised Me by Giving Good Dating Advice. How to Gain Its Insights

Dating via apps has all but made organic setups a thing of the past. Love stories now begin with a swipe on a screen, which is much safer for your ego than getting all dressed up and risking rejection in person. The thrill of IRL love matching may be gone with the Wi-Fi, so how does artificial intelligence play into the dating world now?

When a group of my friends decided to hit the town on a man hunt for a single friend, this long-term married woman was more than down-to-clown. I dusted off my going out shoes, fully prepared to wingwoman from the windows to the walls, until I realized I had literally no idea what I was doing and I hadn’t talked to a strange man on purpose since Instagram was founded nearly 15 years ago.

Here’s how I used ChatGPT, the AI chatbot that uses machine learning and large language models to answer conversational style search queries, to become what I envisioned would be the best wingwoman ever. You can also use ChatGPT to help you build your dating profile.

Does ChatGPT know what a good wingwoman is?

Before I started this exercise, I wanted to make sure the AI tool understood the assignment. “Wingwoman” is one of those terms an AI chatbot could very easily misunderstand, so I asked for its definition as an initial vibe check to avoid it giving me advice on how to best grow wings as a woman or be the most successful female enthusiast of sauced drumsticks.

ChatGPT started off strong by not only defining the term accurately but also offering some insights into what makes a good wingwoman, like being supportive and encouraging and maintaining discretion while on the prowl.

What to wear while wingwomaning

The next bit of our peck and hunt I was nervous about was how I should dress as a part of a larger group of women in an effort to secure the bag for my friend, while also making sure not to appear as competition on the scene. 

Since the ChatGPT response had already touched on this in the “self-assured” bit of the definition, I probed further, using ChatGPT’s language as a baseline to ask about what a good wingwoman should wear and how they should behave.

This was semi-useful advice that I took to heart, deciding to don a cream-colored silk top and a plaid skirt with minimal makeup and accessories instead of a little black dress and a full face. 

Approach with caution

After deciding on the appropriate dress and focusing all my attention on my friend while maintaining a confident yet discreetly supportive and respectful boundary-conscious attitude for the evening (wingwomaning ain’t easy, but it’s necessary), I asked ChatGPT the only question that actually really mattered — how do I approach potential partners on my friend’s behalf or help her hook up without getting in the middle of a sticky situation?

I started by asking ChatGPT if a friend approaching a potential match was a good idea, and if so, what would be the ideal way to break the ice.

ChatGPT was surprisingly thoughtful in the response, offering three very solid instances in which a friend moving in first to lay the groundwork on gettin’ down work would be a benefit to the wingwoman setup: initiating contact if your friend is shy or nervous; approaching as a duo or a group to make the situation less intimidating; and approaching to see if there’s mutual interest before encouraging your friend to engage.

The bot also suggested some ways in which a wingwoman might make the first move for their friend.

Then, ChatGPT laid out some worst case scenarios, just in case I wasn’t already nervous about making a mistake that would ruin the evening: avoiding dominating the conversation and paying attention to body language and verbal cues. 

I headed into the wingwoman night out armed with some pretty decent advice I applied in the wild, but the pickings were a bit slim and most people were engrossed in their mobile devices during any natural break in action where we might approach them.

We used a ChatGPT icebreaker to ask a group of three guys clustered together if they had any good drink suggestions, but the conversation quickly fizzled out. We also tried mentioning the vibe at another bar by chatting up a single man about the view, but that tactic also had very little staying power, as he was continually being approached by people who worked at the restaurant — they seemed to know him as a regular.

And while my friend didn’t meet anyone, we all had a really fun time. I wouldn’t lay the blame on ChatGPT, though. It’s hard to approach men in bars when everyone is on their phones.