What to ask to initiate interesting conversation
Picture this, you are on a date talking about the boring and mundane topics like you do on every first date. You’re bored and uninterested, but the person across from you is good looking- so that date isn’t all that bad. It’s just fine, you probably won’t see them again because it’s forgettable. Then all of a sudden, the person switches up the conversation and asks you something you’ve never been asked before on other dates. Now your interest has been piqued. You’re surprised and thrilled the conversation took a turn for the better, and guess what? You’re having fun answering. The chemistry builds, you get to know the other person better too, it’s fun! You’ll definitely say yes to another date.
If you won the lottery tomorrow, what would the first 3 things you would do with the money?
A good time to swirl this into the conversation would be when you are talking about work. In their answer you’ll find out a few interesting things. Do they play things safe and smart? Like hiring a financial advisor, putting some of the money in an investment? Or give to charity? Or are they more adventurous and say they want multiple homes, yacht or private plane? Follow up with asking where they would buy homes and why. If they play it safe, ask about what charities they would give to and why? The follow up questions to this prompt are endless and also fun.
2. This is pretty embarrassing, but when I am really bored I love doing (xyz). What’s your go to activity when you’re bored?
The saying, “this is pretty embarrassing, but…” is a great prompt to show someone you’re opening up to them. This is great for building a connection because it also shows you feel safe with that person to do so, and sharing something you might not normally share. Insert something a little off the wall here from normal/ status quo hobbies. Think going down YouTube rabbit holes, cleaning, fantasy football, thrifting, gardening, browsing Reddit, going to the public library, etc.
3. Let’s say you won a free trip to anywhere in the world, where would you want to go? Why?
This question helps you identify how adventurous someone is. Is traveling and being a thrill seeker something that is super important for you to find in someone? Or are you a low key person and do not want someone who is adventurous? In their answer, you’ll likely find what you are looking for. Do they want to go hike Machu Picchu and learn all about history? Why’s that? How’d they get into history? Do they want to sail around the Mediterranean Sea and relax? What’s their idea of relaxing? Do they want to go scuba diving with great whites off the coast of Australia? This has the opportunity for so many follow up questions!
Initiating interesting conversation is very important for not just first dates, but throughout the process of getting to know/dating someone. Actually getting a date and meeting someone new is tough enough, and you can’t waste the first date impression with boring chit chat. You need to look as it as an opportunity and take full advantage of being interesting.