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One of the worst feelings is sitting in complete silence with someone — or worse, in a group where the conversation suddenly dies and everyone feels it.
It's hard being the person who makes things awkward, whether it’s because I said something off-putting that killed the vibe or because I didn’t say anything at all. I think of myself as an extroverted introvert: I love being out around people, but I’m just as happy at home binge-watching my favorite show alone.
Lately, I’ve been looking for ways to strengthen the “extrovert” side of my personality, especially in situations where conversation doesn’t come naturally. That led me to focus on improving my conversational skills for those tricky moments.
I put my prompt to use to come up with questions for a first date
My days of swiping, matching, chatting and eventually getting ghosted on dating apps finally ended last year. Since then, my mental state is stronger — and my thumbs are busy typing for work instead of chasing the slim chance of a date.
Still, I’m a firm believer in “stay ready so you don’t have to get ready.” I never want to sit across from someone on a first date while an awkward silence buries any chance of a second one.
To make sure that never happens, I turned to ChatGPT to generate conversation starters based on someone’s interests. You can swap in whatever hobbies apply to the person you’re meeting:
“I'm going on a first date with a woman who enjoys baking, ballroom dancing and cozy video games. Give me 10 good ice-breaker questions I can ask based on those interests.”
ChatGPT started with a smart reminder: the key to a great first date is asking questions that invite stories — not yes-or-no answers. It then generated open-ended questions tailored to each interest, plus a creative bonus: “If your life were a cozy game, would the main quest be baking, dancing or something totally different?”
It even offered flirty follow-up lines, but that’s where I draw the line. I don’t want AI guiding every moment of the conversation. I’m happy to let it handle the ice breakers — the rest is better left to real, unscripted human interaction.
Then I applied it to produce a bunch of questions to ask during a job interview
Another way the prompt can help in social situations is by suggesting smart questions to ask during a job interview. It’s one thing to navigate awkward silence on a first date — it’s another to face dead air when it’s your turn to speak with a potential boss.
To see how this could work, I tried a prompt aimed at preparing for a social media role at a news site:
“I'm attending a job interview for a social media consultant position at Tom’s Guide. Give me 10 thoughtful questions I can ask based on that role.”
Before generating questions, ChatGPT offered useful guidance: strong interview questions should show you understand the brand, think strategically about platforms, care about performance and audience growth, and come across as collaborative rather than interrogative.
The questions it produced covered brand strategy, performance metrics, content workflows and team culture — exactly the areas hiring managers care about.
The takeaway
Using ChatGPT as a preparation tool is one of the main ways i apply it to real-life situations. Using AI in this way helped me stay ready for a potential first date and help me better equipped to speak confidently during a job interview.
It can also aid anyone in plenty of other social interactions, such as chatting with strangers on public transportation, cooking up amusing dialogue with a friend of a friend, your mate’s parents, or even a child or senior citizen who has been put in your care. It’s always best to respond in a natural manner and not let AI completely dictate how you should operate during a conversation.
But it doesn’t hurt to keep some AI-produced ice breakers in your back pocket if you’re trying to make your next meetup as comfortable as possible.
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