Good Questions to Ask a Girl on a Date

You might have thought that plucking up the courage to ask the girl you’ve been interested in out on a date was the most difficult part of the dating experience; while it is hard, it is nothing compared to the awkward struggle of getting to know each other by encouraging each other to talk through interesting questions.

Without first considering what types of questions will get her speaking and opening up about herself, you may find that your first sets of dates are spent with mouths full of sand, nervously worrying about what to say next. Well, since she is likely just as nervous as you, you’ll want to get her talking to help her relax around you, and to get to know her better.

So, to help you along, here are some excellent questions to ask her that will keep the interest strong while dispelling the feelings of discomfort that come as part of the package of dating.

Before we get on with the right questions to ask a girl check out this video of Questions You Should Never Ask a Girl​:

Questions to Ask a Girl on a Date​

Do you have any skills that you keep hidden?

Everybody has certain skills that they keep hidden from the world. It might be that they don’t place much value in them, or that they form part of an activity that only they take an interest in.

Whatever the case is, a great way to get to know someone, and to get them talking, is to ask them about what they are good at. We’re not talking about jobs here, but more about those hidden skills that she might take some pride in.

Is she a gamer, can she draw exceptionally well, does she write, form excellent arguments or is capable of fitting into tight spaces? People are stacked with impressive skills they never talk about, but are just dying to. So, give her a chance to tell you what she is good at; and you might even be surprised.​

Which childhood toy was your favorite?

Getting people to discuss the positive memories in their childhood is a great way to get them to react, and it allows you to level with them on a person-to-person basis. And since we all have them, they are also excellent at keeping a two-way conversation devoid of clichés running during a date.

​So, try asking her about some happy childhood memories like what her favorite childhood toy was. This line of conversation has no pressure or possible undertones to it, making it a perfectly innocuous and relaxing topic to engage in with her.

What was your most embarrassing memory of primary school?

Talking about embarrassing moments can go one of two ways:

Either, it can come across as a means of introducing humor into the conversation to help you both relax and talk freely;

Or it can be an awkward experience that kills the conversation faster than a fart-joke.

The trick to discussing embarrassing moments is to find a way for her to stay detached from them, and what better way is there of doing that than to go as far back as primary school, where we all have hidden stories of very embarrassing moments; thankfully the kind that are funny and not horrible to talk about.

Where in the world would you go if you could?

The topic of travel is always a good one, and by asking the right, open-ended questions, you could keep an inspiring and engaging conversation running for hours. It is also a good way to get her to express her more adventurous side, which will help her to relax and have fun.

The trick to talking about travel is to not make it too vague, and to carry the flow of the conversation with questions like: ‘what do you like about it there; how is the food there, what are the people like; which cities in that country would you like to see, and do you think you could ever live there?'

What did you want to be when you grew up?

We all had grand and naïve ideas of what our career choices would entail once we got slapped in the face by adulthood, although there are those who have managed to live out their childhood dreams.

What dis she want to be when she grew up? How close did she come to achieving it? What got in the way? Does she still think she could do it? These are all interesting questions that blend the past, present and future into one continuously giving topic that encourages her to talk about herself while asking you similar questions.​

Like the question about the child-hood toy, it also gives her an imaginative space where she can remember relaxing memories, and open up a little to you.​

What is the worst job you’ve ever had to do?

Very few people on this planet have had the great fortune of never having to work a crappy job; and everyone’s idea of what makes for a terrible job differs.

Talking about the worst job she has ever had to work will get her chatting about a topic that is likely to generate one or two funny stories, unless of course her worst job is her current one; in which case, you will be giving her a much needed safe-space to vent in.

This question, much like the way too trite ‘so tell me what you do for a living’ cliché will also get you to know a little more about her professional life, without having to sound like you’re reading questions off the back of a badly thought-out cue card.

How do you respond to annoying people?

Even those who see silver-linings in every cloud love to speak about how the general population of Earth gets on their nerves. We all like to imagine that we are not part of the herded masses, and so when we speak about annoying people, it is generally to the praise of ourselves.

How do you get her to feel comfortable then? By getting her to speak about how she handles those from the crowd who get on her nerves.

This immediately puts her above them in her eyes and yours; letting you engage with her in a genuinely interested way, while helping her to relax and be open about her likes, dislikes, strengths and flaws.

Where do you think guys have missed the boat?

Here’s one that will kill two birds with one stone. It will get her speaking about her interest in guys (which will likely be good for you), and will also demonstrate to her that you are not the type to disregard the opinions and needs of women to protect your own masculinity.

So, ask her what she thinks guys in general do wrong when talking to girls, especially when trying to attract them. Besides being able to get a few helpful hints from her, this will. open up an interesting and open-ended line of dialogue for the two of you to follow.

What are your friends like?

There are few things sexier to a woman than a man who takes a genuine interest in her life and friends; and if you are going to end up going steady with her, you’re going to have to get to know her posse at some point or another, so why not start getting to know them by asking her what they’re like.

Getting her to chat about her friends will also feel like you have struck conversational gold since you can be almost certain that she’ll have one hundred-thousand stories to tell.​

Remember though that if she is complaining about them, you should stay neutral in your responses. Why is it not a good idea to agree with her on how bitchy her friends are? She will take their side when her mood changes, and there is nothing more deserving of fear than a pissed of best-friend.​

Which pickup line do you hate the most?

Pickup lines are like the practical jokes of the dating world. They serve little purpose other than to make one party look like an idiot, while the other simply feels awkward. Though despite the commonly felt understanding of this, there are still scores of men out there who try their luck with half-witty quips that generally get them nowhere.

But pickup-lines still have a place in the dating world, though not for practical applications. They do however make for an excellent line of conversation that will get you both relaxed and chuckling in no time.

She has probably been hit with scores of cheesy lines, some of which you might never have heard before; making for an entertaining evening of banter and chatter around all of those guys that made the mistake you didn’t.

This world is full of questions

If struggling for things to talk about on dates is a carefully acquired skill of yours, then the above questions will help get conversation flowing.

Through them you can start coming up with other questions that will get the two of you chatting freely. Remember though to never dominate the conversation, try to keep it clean, and to continually guide the flow of the conversation with interesting and unique questions.

And most importantly: Don’t panic; you’ve got this

Written by Terrence Kennedy

Terrence Kennedy is the man’s man on a journey to self-discovery. A traveler, extreme sports aficionado, an observant wanderer, a DIY-Know-How, an ultimate outsider and a documentarist of culture, sex, dating, relationship, fashion, style and gentleman's etiquette. He has learned a lot through his escapades, and is happy to pass that knowledge on to you.