Getting to know someone and bonding to them.
Great conversation skills open many doors, whether they’re to career opportunities, romance or even scoring yourself a discount on something you want! In a first date scenario, these skills are the difference between awkward silences that make you want to run out the door and sparkling banter that takes things to the next level.
Now, many of us prepare a mental list of questions ready and waiting to pounce at the first hint of silence. While the concept of this is definitely useful, you run the risk of sounding contrived or, worse, like you’re hosting a cheesy dating game show. What you need is context to help bring your questions into conversation.
Before we launch into six great first date questions and how to throw them out there naturally, there are two very important mindsets you need to adopt first.
Being Genuinely Curious
Our minds can play funny tricks on us, especially when we’re overthinking things. For example, of course you’re interested in a guy if you’ve agreed to go on a date. In between that moment and the actual date though, you’ve probably mentally devised a mess of ‘what if’ scenarios and scripted questions straight from a how-to manual. In the process, you’ve forgotten that you are actually very curious about this guy.
Close the door on your future projections. Instead, let your mind ponder things like who he is, what’s on his mind, what he likes doing and what motivates him. Let that genuine curiosity build and take over from any other thoughts. Allowing yourself to be motivated by sincere curiosity about a person leads to natural flow, engagement and sparks that make conversation fly.
Being Present
Even if you’ve got a list of fantastic first date questions in your mind, they’re not going to get you anywhere unless you’re truly present with the answers. After all, it’s the answers that lead to more authentic, stimulating conversations. To really listen to another person, you need to get out of your head and sink into the moment.
The moment doesn’t have anything to do with whether or not he’ll like your questions, what he’ll think of your responses or if you chose the right dress to wear. Those types of thoughts are all to do with the future or the past. When you’re in the present moment, you don’t have past or future thoughts bouncing around in your mind, because it’s open and ready for new information, new responses and new outcomes.
Stay aware of your thoughts and whenever you notice them drifting away from the present, take a deep breath and go back to open curiosity about him and the exciting anticipation of the unknown. That’s half the fun of dates, right? Embrace the unknown, rather than trying to control the outcome with thoughts that take you out of flow with him – and the conversation.
Right. Let’s get that conversation happening with six great first date questions and how to throw them out there.
Question 1
“What’s been the best day of your year so far and why?”
This is a sensational question that should see a guy light up and talk about a day that meant the world to him. As he does, you’re going to learn about some of the stuff that really matters to him. The only problem is, it’s a pretty random question if it comes out of nowhere. So, like all first date questions, ask this when he’s talking about something he’s loved or something that otherwise puts it into context. Here’s how this could play out:
You: So, you’ve been working hard. Have you had time to have fun lately?
Him: Yeah, actually, I got out last Sunday to a go kart day with the boys and it was so much fun. Great seeing the boys and it’s been a couple of years since I’ve karted.
You: I haven’t tried karting but I can’t wait to! That sounds like an awesome day, but what’s been the best day of your year so far and why?
Question 2
“If you could live anywhere in the world, where would you live and why?”
When you’ve already established that you both like travelling, this is a great question and one you’ll both want to vibe on for a while. However, it’s going to sound too weird if you throw it out there in the middle of a chat about the menu. The topic of travel is likely to come up, so wait for that to happen before asking the question:
You: You travel a lot right? Didn’t you just get back from a trip?
Him: Yep, I just got back from a trip to Ayers Rock! Loved learning about the aboriginal culture and the way they live. They’re so tuned in with the land. I’m off to the UK in a couple of months too, which I can’t wait for!
You: That’s so cool, Ayers Rock is definitely on my bucket list and I love the UK. Ok, so you’ve travelled to all these places. If you could live anywhere in the world, where would you live and why?
Question 3
“If you were a superhero, which power would you choose and why?”
This question is really random, but so much fun to get into! Again, you can’t bring it up out of nowhere, but who’s to say superheroes can’t pop up in everyday conversations, as easily as this:
You: I just watched Aquaman on the plane home last week – really cool action scenes underwater! Have you seen it?
Him: Sounds very cool. I have no idea what Aquaman is, but underwater action scenes sound cool anyway.
You: Oh my god, you don’t know Aquaman?! What happened to your childhood, or you just don’t do super heroes?
Him: I did superheroes…I watched Smallville.
You: Hahaha, you totally just watched it for Lana didn’t you?
Him: Possibly…
You: Yeah, well I can’t lie, I even had a crush on her. Tell me, if you were a superhero, which power would you choose and why?
Question 4
“What are the top things you’re most proud of achieving?”
Men love being able to flaunt their achievements and do a little chest beating to impress you. So, why not give him the opportunity to do that, with a question that also lets you know what motivates him? To avoid revealing that it’s on your list of prepared questions, wait until a natural scenario like this comes up:
You: How did you end up doing sales when you started out as such a quiet kid?
Him: It’s actually a cool story. I really had to push myself for a lot of years to get myself out there and I was the worst salesman on the team for over a year. I kept persisting though and it’s now the second year straight I’ve been able to top the charts. So, I’m pretty proud of what I’ve been able to accomplish.
You: Wow, you should be, that’s awesome. So, what would you say are the other top things you’re most proud of achieving in your life?
Question 5
“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 cliche 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?
Question 6
“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.
Him: Yeah?
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 leads 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 sparking. 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.
