App dating has made natural matchmaking a thing of the past. Most love stories now begin with a swipe on a screen, which is much safer for your ego than dressing up and potentially being rejected in the real world. The thrill of real-world love matching may have died completely along with Wi-Fi. So how does artificial intelligence fit into the dating world now?
When a group of friends decided to hit the town to find single friends, this long-married woman was more than just a clown. I dusted off my street shoes and was ready to act as wingwoman from window to wall, only to realize that I literally had no idea what I was doing. It’s been almost 15 years since Instagram was founded, and I’d never purposely talked to a man I didn’t know in that time.
Here’s how I became the best wingwoman I could ever imagine using ChatGPT, an AI chatbot that uses machine learning and large-scale language models to answer conversational search queries. ChatGPT can also help you build your dating profile.
Does ChatGPT know what a good wingwoman is like?
Before starting this exercise, we wanted to make sure our AI tool understood the challenge. “Wingwoman” is one of those terms that an AI chatbot could easily misunderstand, so we asked for its definition as an initial vibe check to make sure the AI wasn’t giving out advice on the best way to grow wings as a woman or how to become the most successful female lover of sauced drumsticks.
ChatGPT is off to a strong start by not only precisely defining the term, but also offering insight into what makes a good wingwoman, including being supportive, encouraging, and remaining discreet while on the prowl.
What to wear when wingwoman
What made me nervous about the next part of our pecking and hunting was how to dress as part of a large group of women to secure a bag for a friend, while at the same time being careful not to look like a competitor on the spot.
ChatGPT’s response already touched on this in the “confidence” part of their definition, so I used ChatGPT’s language as a guide to ask for more details about how a good wingwoman should dress and behave.
It was a semi-helpful piece of advice that I took to heart: Instead of wearing a black dress and covering my entire face, I decided to wear a cream silk top and a plaid skirt, with minimal makeup and accessories.
Approach with caution
After picking out the right dress and giving my friend my full attention that night while remaining confident, unobtrusive, supportive, respectful and boundary-conscious (being a wingwoman isn’t easy but it’s necessary), I asked ChatGPT the only question that really mattered: how can I approach potential partners on my friend’s behalf or help them meet without getting into sticky situations?
First, we asked ChatGPT whether it’s a good idea for friends to approach potential matches, and if so, what’s the ideal way to break the ice?
ChatGPT gave an amazingly thoughtful response, giving three very solid examples of how a wingwoman setup would benefit from a friend making the first move and laying the groundwork for work: reaching out if your friend is shy or nervous, approaching in a dyad or group to make the situation less intimidating, and approaching your friend to see if there’s mutual interest before encouraging them to get involved.
Bott also suggested some ways wingwomen can make the first move for their friends.
ChatGPT then presented me with some worst-case scenarios, in case I wasn’t already feeling anxious about making a mistake that would ruin the night: try not to dominate the conversation, pay attention to body language and verbal cues, etc.
I headed out to Wingwoman’s night out armed with some pretty good advice I’d applied in the field, but the options were a little sparse and most people were glued to their mobile devices during any natural breaks in the action we might approach.
I tried using ChatGPT’s icebreaker to ask a group of three guys if they had any good drink suggestions, but the conversation died down quickly. I also tried talking to one guy about the view to get a feel for the atmosphere at another bar, but that tactic didn’t last very long either, as restaurant employees kept coming up to him. They seemed to know him as a regular customer.
Although I didn’t see any of my friends, we all had a great time. I don’t blame ChatGPT though, it’s hard to approach guys in a bar when everyone is on their phones.
