Unlocking the Secrets to Love: 6 First Date Questions and Conversation Starters

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Valentines week is just around the corner; the season of first dates. Take a look at the best first date questions to ask him and make him fall in love!

One of the best ways to make sure that your date goes well with the guy you like is by getting to know him better. And what better way is there than asking him some fun great first date questions that will help you know him inside out, and how he is as a person?

How do you feel when you talk to a guy whoโ€™s engaged, energetic, and full of curiosity about you?

Along with totally enjoying the convo, itโ€™s possible that youโ€™ll feel compelled to reveal your personality to this person, by sharing your passions, values, and opinions. When this happens, you start to achieve the goal of dating. And, whatโ€™s that?

Getting to know someone and bonding to them.

Great conversation skills open many doors, whether theyโ€™re 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 youโ€™re hosting a cheesy dating game show. What you need isย contextย to help bring your questions into the conversation.

Before we launch into six deep first date questions to ask men and how to throw them out there naturally, there are two very important mindsets you need to adopt first.

Related: 10 Things To Look For On A First Date

Being Genuinely Curious

Our minds can play funny tricks on us, especially when weโ€™re overthinking things. For example, of course, youโ€™re interested in a guy if youโ€™ve agreed to go on a date.

In between that moment and the actual date though, youโ€™ve probably mentally devised a mess of โ€˜what ifโ€™ scenarios and scripted questions straight from a how-to manual. In the process, youโ€™ve forgotten that youย areย actually very curious about this guy.

Close the door to your future projections. Instead, let your mind ponder things like who he is, whatโ€™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 the natural flow, engagement, and sparks that make conversation fly.

Being Present

Even if youโ€™ve got a list of fantastic first date questions in your mind, theyโ€™re not going to get you anywhere unless youโ€™re truly present with the answers.

After all, itโ€™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 doesnโ€™t have anything to do with whether or not heโ€™ll like your questions, what heโ€™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 youโ€™re in the present moment, you donโ€™t have past or future thoughts bouncing around in your mind, because itโ€™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. Thatโ€™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 โ€“ and the conversation.

Letโ€™s get that conversation happening with six good first date questions and how to throw them out there.

Here Are 6 Great First Date Questions To Ask A Man

Question 1

โ€œWhatโ€™s been the best day of your year so far and why?โ€

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, youโ€™re going to learn about some of the stuff that really matters to him. The only problem is, itโ€™s a pretty random question if it comes out of nowhere. So, like all first date questions, ask this when heโ€™s talking about something heโ€™s loved or something that otherwise puts it into context.

Hereโ€™s how this could play out:

You:ย So, youโ€™ve been working hard. Have you had time to have fun lately?

Him:ย 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 itโ€™s been a couple of years since Iโ€™ve karted.

You:ย ย I havenโ€™t tried karting but I canโ€™t wait to! That sounds like an awesome day, but whatโ€™s been the best day of your year so far and why?

Related: 20 Questions To Ask A Guy To Get Closer

Question 2

โ€œIf you could live anywhere in the world, where would you live and why?โ€

When youโ€™ve already established that you both like traveling, this is a great question and one youโ€™ll both want to vibe on for a while. However, itโ€™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:ย You travel a lot right? Didnโ€™t you just get back from a trip?

Him:ย Yep, I just got back from a trip to Ayers Rock! Loved learning about the aboriginal culture and the way they live. Theyโ€™re so tuned in with the land. Iโ€™m off to the UK in a couple of months too, which I canโ€™t wait for!

You:ย Thatโ€™s so cool, Ayers Rock is definitely on my bucket list and I love the UK. Ok, so youโ€™ve traveled to all these places. If you could live anywhere in the world, where would you live and why?

Question 3

โ€œIf you were a superhero, which power would you choose and why?โ€

This question is really random, but so much fun to get into! Again, you canโ€™t bring it up out of anywhere, but whoโ€™s to say superheroes canโ€™t pop up in everyday conversations, as easily as this:

You:ย I just watched Aquaman on the plane home last week โ€“ really cool action scenes underwater! Have you seen it?

Him:ย Sounds very cool. I have no idea what Aquaman is, but underwater action scenes sound cool anyway.

You:ย Oh my god, you donโ€™t know Aquaman?! What happened to your childhood, or you just donโ€™t do super heroes?

Him:ย I did superheroesโ€ฆI watched Smallville.

You:ย Hahaha, you totally just watched it for Lana didnโ€™t you?

Him:ย Possiblyโ€ฆ

You:ย Yeah, well I canโ€™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

โ€œWhat are the top things youโ€™re most proud of achieving?โ€

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 itโ€™s on your list of prepared questions, wait until a natural scenario like this comes up:

You:ย How did you end up doing sales when you started out as such a quiet kid?

Him:ย Itโ€™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 itโ€™s now the second year straight Iโ€™ve been able to top the charts. So, Iโ€™m pretty proud of what Iโ€™ve been able to accomplish.

You:ย Wow, you should be, thatโ€™s awesome. So, what would you say are the other top things youโ€™re most proud of achieving in your life?

Related: 50 Questions To Ask A Girl to Get to Truly Know Her

Question 5

โ€œIf you never had to work again, how would you spend your time?โ€

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:ย So, you love your job?

You:ย Yeah, I really do. Itโ€™s so fulfilling to be up on stage and as clichรฉ as it sounds, it honestly just makes me feel alive. How about you?

Him:ย I do enjoy it. Itโ€™s not something Iโ€™ll do forever, but it challenges me for right now and itโ€™s got me on a good pitch financially.

You:ย Thatโ€™s cool. So, what if you never had to work again and money wasnโ€™t a factor? How would you spend your time?

Question 6

โ€œWhat has been your best moment in your job?โ€

Youโ€™ll seriously see a person light up when you ask a question about what really inspires them. Itโ€™ll also give you some clear insight into this side of them, in terms of whatโ€™s important in life.

To pop it in naturally, let it flow into a work conversation:

You:ย How long have you been a vet for?

Him:ย About three years now. Itโ€™s a really cool job with a lot of different challenges.

You:ย And whatโ€™s been your best moment as a vet?

What If You Donโ€™t Spot A Natural Segue?

While itโ€™s always best to let questions flow naturally into the 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 itโ€™s random.

That means, if he questions you on the randomness of it, youโ€™re not going to stutter while thinking, โ€œwell, it was on my previously prepared questions listโ€ฆโ€.

Hereโ€™s how to do it:

Him:ย Yeah, all is going well at work and Iโ€™m excited for the next challenge.

You:ย Thatโ€™s very cool. Ok, now I have a random question I want to ask.

Him:ย Yeah?

You:ย Tell me, if you could live anywhere in the world, where would you want to live and why?

Him:ย That is a random question.

You:ย Hahaha, I know. I love travel so much, and I think the country youโ€™d love to live in says so much about a person. So Iโ€™m totally reading your answers.

Him:ย Ok, well, I suppose Austria. Iโ€™ve never been but Iโ€™ve always heard amazing stories from my dad about how beautiful it is and how amazing the people are.

You:ย Austria hey?

Him:ย Hahaha, yeah. What can you read from me about that?

You:ย I canโ€™t reveal that, Iโ€™d be making it too easy for you!

Related: 50 Red Hot Conversation Starters To Spice Up Your Date

Whatโ€™s happening here is that youโ€™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, youโ€™ll find that segues magically present themselves to keep the conversation sparkling.

Before you know it, youโ€™ll be saying goodbye to that โ€˜first date questionsโ€™ list and opening up to conversations that take you toward real connection. Have a happy Valentineโ€™s day!

Want to know more first date questions that you can ask a guy? Check this video out below!

Check out Mark Rosenfeldโ€™s personalย websiteย andย blog, for more interesting, helpful, and informative pieces.


Written By Mark Rosenfeld 
Originally Appeared In Make Him Yours
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