Lifestyle, Personality / July 6th, 2015

9 Questions to Ask on a First Date | How to Engage With Her

Going on a first date can bring forth all sorts of emotions.

Excitement and happiness are the good ones and we welcome these feelings with open arms.

Too bad we have a lot more negative emotions pushing their way into our mind such as fear and dread.

I used to be like this. I was always thinking of the worst-case scenario and trying to think of ways to avoid them at all costs on a first date.

Don’t lie; you probably still have panic attacks the hours just before a first date.

On one hand, most of the fears we have on a first date are unrealistic. However, there is one scenario we should be concerned about as it happens MUCH too often.

The inability to keep an ongoing, engaging conversation is an absolute relationship killer. I’m pretty sure every guy had to experience this awkward and embarrassing situation at least once in his life, I know I have.

What makes this frightening is how easy this can continue to happen. To calm your nerves, I can assure you that it doesn’t have to be this way.

This article will provide you with 9 questions to ask on a first date that will provoke engaging conversation and have her thinking you are the most interesting man in the world.

Let’s dive right into it.

1. What did you fear when you were younger? (And have you conquered your fear?)

This is a question everyone can relate too.

I love this question as you will get a response that will be in the form of a story compared to just a one word answer. This will also enable you to share your experience of what scared you when you were a little one, instantly building a connection.

If you’re really good, you can offer some light advice (with some humor) on ways she can overcome her fear if she hasn’t already.

2. What are your biggest pet peeves?

There is at least one thing that frustrates every lady and most of them love venting about it!

This is your chance to start off a whole new interesting conversation.

If this just brings up a one-word response, gently prod her to share an experience where this pet peeve occurred in the past. Just be careful and try to read her body language throughout, if she doesn’t want to open up change course.

Learning about your dates pet peeves is a great way to find out any deal-breakers early on and avoid them being exposed after you invested a good chunk of time.

3. What were you like as a child?

If you want to build a great connection with your date, learn as much as you can of their younger years without being creepy about it.

One of my favorites is asking how your dates were like as a child. This question gives you an inside look at her personality when interacting with members she’s closest with.

Adults also tend to act like their earlier selves when angry so this might give you a (scary?) glimpse into the future!

4. Who is your biggest role model?

It’s a good idea to keep your date in a happy mood and what better way than by her talking about someone she admires?

Most women have a close relationship with one of their parents so expect either her mom or dad to be the answer here. However, it’s not unusual for a friend or celebrity to be her top choice.

Ask her why this person inspires her. Look for a response in the form of a personal story. Follow up with an explanation of your own about your role model to further cement that important spark.

5. What’s next on your travel list?

I’m sure they are out there somewhere…. but I have yet to meet a woman that didn’t like to travel and explore the world.

This makes this question a safe one to ask.

Once she responds follow up with why she wants to go there.

You will earn so much bonus points if you are a well travelled man. Even better if the destination she wants to visit is one you already experienced. Think about it, you can give her a first-hand look on what to expect when travelling to this destination. Be honest in your review and tell her some personal stories of your journeys and just watch the excitement leap from her face.

6. Are you a morning or night person?

A question that will give you one answer or the other so it’s pretty easy to prep for.

I personally am a night owl but do find my best work is done in the morning. With that said, I HATE being bothered in the morning especially when I’m still half asleep and haven’t got any coffee in me yet.

Given that there are only 2 possible answers for this, I like this question as it provides a 50/50 chance you guys have something in common. Take as many early wins as you can!

7. Were you popular in school?

Be careful with this one as it can bring up bad experiences. If you sense this at all from her body language, change course!

With that said, this is a fun question to ask and one she should be excited to share. People love talking about themselves especially when they were/are admired by others.

On the other hand, it could give you a subtle hint on how shallow she is as a person. Don’t take this question too seriously and have some fun with it.

Take some time to share how popular you were during high school. Keep her laughing regardless and you’ll win her over.

8. What do you like to do when you’re not working?

This is probably my favorite question to ask a girl on a first date. You’re basically asking a girl what she likes to do on her spare time but in a more creative way.

Think of your own life, you most likely separate it between what you do for work and what you do for leisure. Your date most likely has her life categorized the same so this is a great question to learn what her passions are.

Don’t forget what she likes to do! This question will work wonders for you down the road when planning future dates.

9. What’s on your bucket list?

To expand on the previous question ask her the things she would plans to do before she kicks the can.

Women like men who rack up experiences and have plans for further achievements in life. Asking this question demonstrates your interest in goal setting as well as in her. A win-win!

Now go out there and impress your date!

These 9 questions are a great start but there are countless others you can use to avoid potential awkwardness that can creep up on you from silence. Be engaging, charismatic but above all else LISTEN. Women want to be heard so don’t think you can get away with zoning out every two minutes.

Have a big date coming up? Let me know the results! Either leave a comment below or send an email to info@timelessgent.com. I would love to hear from you.