The key is to come prepared.
Sometimes, it just happens, naturally. Sometimes, it just does not.
We have all been there. A restaurant outing that just falls flat, a birthday dinner where the conversation just does not flow.
You would be surprised, but the key, really, is asking the right questions. Just like a good interviewer. Questions will help you discover things about the other person (whether a new acquaintance, or even your spouse, your child, your co worker, your sibling, your parent)
You will be amazed by the answers and by how your questions will automatically turn into deeper, more interesting, conversations. We tend to forget to have these conversations with the people that are closest to us. And coming ready, having these prompts, at times, is the key to getting there.
Obviously, pick and choose what works for you.
“What is something you wish you knew and didn’t have to learn the hard way?”
“ Where would you like to live for a season, if you had the choice?”
“What is one regret you have?”
“Who is a role model for you?”
“Tell me 3 things on your bucket list”
“What trait would you want to change about yourself?”
“What is the best gift you have ever gotten?”
“What is the best part of your day, and why”
“What is your biggest fear?”
Ask the birthday kid, or spouse “ what was the highlight of this past year?” “ What are you looking forward to in the coming year?”
“What was the most embarrassing thing you did at school as a kid?”
“What’s your favorite Yom Tov and why?”
“What is your favorite Mitzvah and why? What is the hardest mitzvah for you to keep, and why?”
“If you could travel back in time and observe an historical event, which one would you choose?”
“If you had a chance to be invisible for a day, where would you go?”
“What is your ideal way to celebrate a birthday?”
“If you won the lottery, what would you do?”
“What do you like most about yourself and why?”
“If you could go back and talk to yourself as a child, what would you say?”
“Which language, sport, trait, instrument, skill…. Would you like to learn if time and money wasnt an issue?”
Please feel free to add your conversation starters in the comments section below!
Thank you for a great article!
I love this topic always have this problem of what to talk about!
Just as a by the way there is such a game out there called the ungame
Thank you! i’m always unsure how to take it to the next level from small talk. I tried this on my husband and it worked!
Just don’t come too prepared, unless this is for a date.
Just a small thing to point out for a married relationship. Obviously we all want deeper and more meaningful conversation and connection but if we’re going to measure the success of an outing based on how the conversation is we’re bound to be disappointed… trying to focus instead on the intrinsic connection we already have and just enjoying the time together as is, even if some of it is in silence or trivial conversation can be helpful . If deeper conversation evolves that’s great but sometimes trying too hard or really setting it as an expectation can ruin an otherwise beautiful outing. Not my own thought, just something i learned from relationshift that really resonated..