AI Gave Me Surprisingly Good Dating Advice. How to Gain Its Insights

App dating has made organic fixations all but a thing of the past. Most love stories now start with swipes on a screen, which is much safer for your ego than getting dressed up and potentially rejected in real life. The thrill of IRL love matching may have officially died with Wi-Fi. So how does artificial intelligence play a role in the dating world now?

When a group of my friends decided to hit the town in search of a single girlfriend, this long-married woman was more than down to clown. I dusted off my going-out shoes, all set to wingwoman from windows to walls, until I realized I literally had no idea what I was doing and that I had not intentionally talked to a strange man since Instagram started almost 15 years ago.

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

Does ChatGPT know what makes a good wingwoman?

Before I started this exercise, I wanted to make sure the AI ​​tool understood the task. “Wingwoman” is one of those terms that can be very easy for an AI chatbot to misunderstand, so I asked for the definition as an initial vibe check to avoid it giving me advice on how to best grow wings as a woman or become the most successful female gravy drumstick lover.

ChatGPT started strong by not only precisely defining the term, but also providing insight into what makes a good wingwoman, such as being supportive and encouraging and remaining discreet while roaming.

What to Wear While Wingwomaning

The next part of our search that I was nervous about was how to dress as part of a larger group of women to secure the bag for my girlfriend, but also to make sure I didn’t come across as competition.

Since ChatGPT’s answer already touched on this in the ‘confident’ part of the definition, I investigated it further. I used ChatGPT’s language as a starting point to ask what a good wingwoman should wear and how she should behave.

This was a pretty useful piece of advice that I took to heart and decided to wear a cream 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 what dress to wear and focusing all my attention on my girlfriend, while maintaining a confident yet discreet, supportive and respectful attitude that evening (wingwomaning isn’t easy, but it is necessary), I asked ChatGPT the only question that really mattered: how can I approach potential partners on my girlfriend’s behalf or help her do something without getting into an awkward situation?

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

ChatGPT responded in a surprisingly thoughtful manner, giving three good examples of where a friend is given the space first to lay the groundwork for the work, which would be an advantage for the wingwoman setup: take the initiative yourself if your friend is shy or nervous; approach them as a duo or group to make the situation less intimidating; and approach them to see if there is mutual interest before encouraging them to join in.

The bot also suggested ways a wingwoman could make the first move on her boyfriend.

ChatGPT then outlined some worst-case scenarios, just in case I wasn’t already afraid of making a mistake that would ruin the evening: don’t dominate the conversation and pay attention to body language and verbal cues.

I went to the wingwoman evening with some good advice that I had applied in the wild, but the choice was limited and most people were engrossed in their mobile devices by the time we could keep an eye on them.

We used a ChatGPT icebreaker to ask a group of three guys sitting together if they had any suggestions for a good drink, but the conversation quickly fizzled out. We also tried mentioning the atmosphere at another bar by approaching a single guy about the view, but that tactic also had little effect, as he was constantly approached by people who worked at the restaurant — they seemed to know him as a regular.

And even though my girlfriend didn’t meet anyone, we all had a great time. I wouldn’t blame ChatGPT. It’s hard to approach guys in bars when everyone is on their phones.