Conversation can be a tricky thing to master. It changes depending on the situation, and if you don’t know the other person very well, it can falter, leaving you feeling awkward. Add into that a woman that you’re interested in, and the awkwardness factor shoots right up! Is it any wonder that these are some of the most searched for phrases on Google:

  • Best questions to ask a girl
  • Cute questions to ask a girl
  • Hot questions to ask a girl

It’s easy to fall into the trap of thinking that girls are some other alien species, but they’re really not. Plus, they’re not girls, they’re women- grown-ups, just like you! They have interests, passions, things that make them mad, and things they love- just like you.

Questions to ask

So, arm yourself with our arsenal of questions guaranteed to keep the conversation flowing, and remember, if she tells you she doesn’t want to talk, be respectful. There’s a huge gap between being a conversational Lothario and a creep- make sure you know the difference!

Questions to Ask Someone You Just Met

If you’ve just been introduced to someone that you’d like to get to know better, these questions could help you open up that conversational doorway. These are questions for first-time meetings that allow you to find out a little more about her. Don’t be afraid to smile and ask a question!

So, how do you know (insert name here)?

Let’s start with an easy one. You, presumably, know this person through a friend, family member, or colleague. Use this question to find out what connects you, and you’ll probably find plenty more to talk about. If you’re really nervous, ask your friend to introduce you.

Wow, this place is amazing! Is this your scene?

The great thing about this is it doesn’t matter if she says “yes” or “no.” You’ve expressed an interest in her opinion. Don’t ruin it by being fake! If she says she hates it, don’t backtrack and say, “Oh yeah, me too.” Smile and ask what’s so bad about it, and you’ll be chatting in no time.

Questions to ask

Do you like this song?

So simple, yet it gets people talking about music, a primal creative force that is intrinsically connected to emotion. Maybe drop this question into the conversation when you see this woman bopping along to something, particularly if it’s a song you love too- instant common ground. Maybe you could even ask them to dance?

I didn’t catch what my friend said before. What is it that you do?

If they give you a one-word answer, ask if she likes the job and what it entails. Judge the mood; if she hates her job, she might not want to discuss work- move on! But if she’s passionate about her career, she’ll be pleased with your interest. Let her ask you about your job, too, and share funny stories if it seems appropriate.

Questions to Ask a Crush

Any of the above questions could apply here, with the caveat that it’s important to make your intentions known fairly quickly. Kick fear of rejection to the asphalt and be as straight up as possible. Remember, everyone appreciates honesty.

Would you like to grab a coffee?

Straight to the point, everyone knows it means you’re interested in being more than friends. Boom.

What’s your favorite food?

Everyone loves talking about food. The great thing about this question (asked mid-flow- don’t just walk up to a random person and ask this!) is it leads to “Oh I know a great place that serves…” and the suggestion of a date.

What do you look for in a guy?

Again, this needs to be asked once a conversation has been established, but this has the double whammy of letting her know you’re interested in her taste in men, plus you’re keen to get to know her likes and dislikes.

Questions for Sedate Parties

Whether it’s Thanksgiving with extended family and friends or a quiet get together to celebrate a cousin’s promotion, there are plenty of polite events that require decorum and sensitivity. Here are our favorite questions that keep your new friend talking while remaining in key with the tone of the occasion.

What are you drinking?

What is that exotic cocktail/glass of wine/unusual looking craft beer? Whatever it is, offer to get her another. Bond over your love of single malt, or unusual gins. Alcohol in moderation is a thing to be savored and enjoyed, and even a good mocktail can be a great talking point.

What’s really getting to you these days?

This can be tailored to the event; everyone knows politics always comes up around the dinner table (why, oh why!), or it could be on the back of someone else’s rant about the terrible service at a favorite restaurant. Have fun sharing hilarious stories about annoying things that have happened to you over the week.

Who’s had the biggest impact on your life?

A question for deeper into the conversation, perhaps. Remember to share your own, too.

Questions for Rowdy Parties

Ok, the cold beers are flowing, and everyone is howling with laughter; how do you stand out from the crowd? We explain how to keep your truth or dare questions clean and your never have I ever questions dirty- or at least interesting!

What can you do that no one else can?

Prepare to be surprised, grossed out, or even intrigued by the answer!

Never have I ever broken the law

And, if she drinks, you demand to know the story! Swap this out for anything:

  • Never have I ever had a one night stand.
  • Neverhave I ever had money stolen.
  • Never have I ever played seven minutes in heaven.

And so forth. Use your imagination; everyone loves to share wild stories at parties.

Truth or Dare: If you were a man for a day, what would you do?

Be prepared to get asked the opposite question right back, and don’t be too crude- too many guys say they’d sit in the house fondling themselves, and no woman wants to hear that!

Questions for a First Date

First dates are undeniably nerve-wracking. Even if you’re normally quite verbose, the nerves can turn you into a silent, quivering mess. It’s ok. Breathe! Now, here are some things to ask the woman who liked you so much she’s gone for dinner or a show with you.

Who are you closest to in your family?

A great way to pose this question is to talk a bit about your own family first. It’s a natural part of opening up, but don’t worry, neither of you has to bring the skeletons out of the closet just yet! Talking about who is important to this person will give you an insight into what makes her tick.

What’s the best gift you’ve ever received?

Ok, yes, there are ulterior motives for this question if you see something long term with your date. However, the key thing about this question is it will remind your potential partner of a happy moment, something that made them smile. You could switch it up to the best gift given, instead.

What’s the weirdest dream you’ve ever had?

First dates are great times to pop out leftfield questions as you both know that it’s important to keep the conversation flowing. Get a glimpse into her subconscious, and be prepared for weirdness!

Questions About Life

These are questions for any situation where you are getting to know someone. They’re great for traveling together in a group, work nights out, pretty much any social gathering, and of course, that all-important first date (see above). Showing a woman that you are interested in her as a person means she’ll likely return the favor, and it could spark one of the most insightful conversations of your life.

What’s your biggest ambition right now?

Everyone has ambitions- at what age do we stop thinking about amazing things we want to do? Never. Find out what she wants to do with her life, and encourage her to share how she’s going to achieve it or what steps she’s already taken. When you talk about your own ambitions, be honest, but don’t deliberately try to outshine hers. Everyone’s goals are valid.

If you could go back in time five or ten years, would you change anything?

This seems like a throwaway question, but it’s actually quite deep. It tells you if this person is happy with their life, or if they have regrets. It can really get the conversation flowing, especially if they have one or two things they would want to change.

Have you got any phobias?

Phobias are deeply personal and a great way to get to know more about someone. Be supportive and be prepared to admit your own fears- no matter how ridiculous you think they are! Yes, even you with the fear of peanut butter sticking to the roof of your mouth.

What makes you angrier than anything else in the world?

People love to talk about what makes them mad! It could be injustice, it could be world hunger, or it could be that the guy on the corner never puts enough mustard on the ‘dogs. Don’t judge her for being petty- join in with your own first world problems! People bond over shared troubles as much as they do over shared happiness.

If money were no issue, what would you be doing with your life?

This is an extremely revealing question. Most of us, if we’re honest without ourselves, would not be in exactly the position we’re in if not for the need for money. Or, at the very least, we have other passions we wish we could pursue. This question gets her to really think about what’s important to her and can open up a real doorway into her soul.

The key thing to remember is such a cliché but still so true: be yourself. There’s no point faking it with someone you want to get closer to. They’ll only figure out that’s not the real “you” in time and wonder what was going on. Relax, open up, and be prepared to be asked some probing questions yourself! Above all, enjoy your new conversation questions and be ready to make great friends as well as find potential partners.