How to Start a Conversation with Anyone at Any Time

There have been many moments in my life when I've wanted to start a conversation with someone but was too scared. Either I didn't know how to start the conversation, or I didn't know what to say based on the person's response, and looking dumb was the last thing I wanted to do.

Throughout my life, I've made the same observation — certain people seem to have a natural gift for conversation. They effortlessly ask engaging questions, deepen discussions, and navigate awkward pauses with ease. For many of us, this ability can seem almost genetic; if you don't naturally have it, you might believe you never will.

Even today, I still struggle to approach people I don't know. I always fear that my insecurities will come out, the other person will notice, and I will feel judged.

A few years ago, however, I stumbled upon a little trick that I frequently use. It has been incredibly impactful in making me feel comfortable enough to start a conversation with anyone.

Ask a Question You Already Know the Answer To

The trick is to ask someone a question you already know the answer to. Therefore, since you already know what the person is likely going to say, you can have a few follow-up questions prepared. Basically, you're creating the flow of the conversation ahead of time, and it feels almost like you're reading lines rather than having to improvise.

For example, if you're in class and want to talk to someone, you can ask someone what the teacher just said about the homework. In actuality, you know what the homework is, so you know what the person is going to say. Then, you can have other follow-up questions prepared, like "Did you do it already?" "Was it hard?". If it is a hard assignment, you can make a joke about how you'll do badly on it or how the teacher is always punishing you. Again, you can sort of plan all these lines out ahead of time.

Another example would be at the office. Maybe your boss just said something in a meeting you heard, but you pretend you didn't, so you ask a coworker to remind you.

Even if you're attending a meetup with a bunch of random people, maybe you can find someone's Instagram or LinkedIn ahead of time and ask them if they've been on any vacations recently, knowing that by a recent Instagram picture they have, or you can ask someone what they do for work, knowing that they're already a chef at a nearby bakery.

There are countless examples of use cases and many ways you can executive this strategy to your own liking.

Either way, it's really helpful to reasonably predict one or two answers from the person you're starting a conversation with and have those first few questions prepared.

I guarantee this works exceptionally well in almost every situation, and if there's someone you've been wanting to talk to for a long time, give this method a shot.

You'll be happy you did!

P.S. Feel free to try this strategy on nufriends!!