“If you never had to work again, how would you spend your time?”
This question is perfect to prompt him to open up about his values, so you can see what really drives him. To put this one in context, wait for an opening in a conversation about his or your work to lead you in:
Him: So, you love your job?
You: Yeah, I really do. It’s so fulfilling to be up on stage and as cliché as it sounds, it honestly just makes me feel alive. How about you?
Him: I do enjoy it. It’s not something I’ll do forever, but it challenges me for right now and it’s got me on a good pitch financially.
You: That’s cool. So, what if you never had to work again and money wasn’t a factor? How would you spend your time?
“What has been your best moment in your job?”
You’ll seriously see a person light up when you ask a question about what really inspires them. It’ll also give you some clear insight into this side of them, in terms of what’s important in life.
To pop it in naturally, let it flow into a work conversation:
You: How long have you been a vet for?
Him: About three years now. It’s a really cool job with a lot of different challenges.
You: And what’s been your best moment as a vet?
What if you don’t spot a natural segue?
While it’s always best to let questions flow naturally into conversation, sometimes you just really want to ask something! It is possible to go straight into it. The key is to show you have the social awareness to know that it’s random. That means, if he questions you on the randomness of it, you’re not going to stutter while thinking, “well, it was on my previously prepared questions list…”.
Here’s how to do it:
Him: Yeah, all is going well at work and I’m excited for the next challenge.
You: That’s very cool. Ok, now I have a random question I want to ask.
You: Tell me, if you could live anywhere in the world, where would you want to live and why?
Him: That is a random question.
You: Hahaha, I know. I love travel so much, and I think the country you’d love to live in says so much about a person. So I’m totally reading your answers.
Him: Ok, well, I suppose Austria. I’ve never been but I’ve always heard amazing stories from my dad about how beautiful it is and how amazing the people are.
You: Austria hey?
Him: Hahaha, yeah. What can you read from me about that?
You: I can’t reveal that, I’d be making it too easy for you!
What’s happening here is that you’re being honest and lighthearted about the randomness of your question, rather than awkward and trying to hide the fact that you want to know the answer. Your authenticity and genuine curiosity lead to a flowing conversation.
Just remember, when you stay in the vibe of open, sincere curiosity about him and sink into the moment, you’ll find that segues magically present themselves to keep the conversation sparkling. Before you know it, you’ll be saying goodbye to that ‘first date questions’ list and opening up to conversations that take you towards real connection.
Want to know more first date questions that you can ask a guy? Check this video out below!
Written By Mark Rosenfeld Originally Appeared In Make Him Yours