Do you find yourself at a loss for words whenever you go on a first date? Starting a conversation can be difficult, especially when you know nothing about the woman sitting across from you.
At the same time, it can be a prime opportunity to open up and talk about damn near anything. Since you are both new to each other, you have free reign to ask any questions that pop into your head.
Many men ask a set group of questions whenever they go on a first date with a woman. This is fine, but you must ask yourself what you get from them.
Talking about favorite foods and movies is all well and fine, but these things aren’t giving you a great deal of insight into the type of person she is.
The key in these situations is that you want to ask questions that are deep enough that they’ll get her (and you) to open up but aren’t so deep that they’re going to make the conversation tense. You’re not trying to get her life story; you’re trying to get to know her better.
Figuring out what questions to ask directly relates to what’s important to you.
Let’s go back to favorite foods and movies for a second. Yes, it’s true that for most people, these are just casual topics of conversation, but that isn’t the case for everyone.
For example, if you work as a professional chef at a Michelin-star restaurant, chances are you have more than a passing interest in food. If you appreciate fine dining that the average person lacks, that’s something you should know about her as soon as possible.
Similarly, don’t ask questions just for the sake of being polite. If your first date is the Monday after Superbowl, but you have no interest in football, there’s no point in conversing about it.
You have to ask the questions that are important to you.
Always be honest and always be yourself, especially when you’re just getting to know the person. The only questions worth asking are the ones you legitimately want to hear the answers to.
Still, dates can last for quite a while, and even if you ask every question that pops into your head, you might still find yourself sitting there in awkward silence.
It always pays to have a plan to keep the conversation going. You don’t want to rely on generic or cliché questions, but you also don’t want to ask things so specific that they put her on the spot.
Here are 12 questions you can use to naturally get the conversation flowing while getting a greater insight into the woman sitting across from you.
1. What is your favorite thing about where you grew up/your childhood?
People often ask questions like, “Where are you from?” or “When did you move here?” These are fine, but consider following up with something deeper and more open-ended on a date.
Asking her about her childhood can give you great insight into the type of person she is and what she values. Does she mention having lots of friends? Family vacations? Playing sports? Spending a lot of time at home by herself?
All of these could be a great indication of how compatible the two of you will be. If she was a homebody during high school and you were an extrovert who loved going out and socializing, it could be a sign that you might not be compatible.
Of course, people are always subject to change, but this is a great way to explore your similarities and differences casually.
2. What place do you want to travel to the most?
Travel can be a touchy subject for many people. Some people are explorers who have visited 25 different countries, while others have never even left the country.
I’ve met many men who are self-conscious about not being as cultured as some women out there. Reframing the travel question into something like the question above can be a great way to alleviate that pressure.
And again, use these questions as an opportunity to read into her a little bit. The ideal vacation is different for everyone. Some people like to lie in the sun at a beach resort for two weeks straight, while others like to backpack across Europe.
Which camp do you fall into? If either of these ideas repulses you, it’s better to find out sooner rather than later.
3. Are you a morning or an evening person?
As you get older and have more dating experience, you begin to realize the things you once thought were minor differences make or break the relationship. For example, if you are a morning bird and the other is a night owl, be prepared for some friction.
It might sound silly initially, but everyday activities like grocery shopping lead to arguments between couples. And what’s even worse is that you’ll probably be months or years into a relationship before you realize you are completely incompatible.
Far too often, one person in a relationship feels forced to change their routine because ordinary tasks end up causing friction.
If your routine is to wake up at five in the morning, run for an hour, then go to the grocery store as soon as it opens, suddenly having to shop after work or on the weekends can be a significant shift. Something that used to take you 20 minutes now takes two hours, and you begin to resent it.
Do whatever you can to gauge if your living styles and routines will be congruent.
4. What do you love most about yourself?
This is a big one. It might sound a bit cliché, but no person on the face of the planet can be happy in a relationship unless they are happy with themselves. Self-confidence issues aren’t usually on display during the first date—or even the second or third—but they can destroy a relationship in the long run.
It’s usually years before deep-rooted self-confidence issues become apparent. We all have things that we need to work on, and the woman you’re dating is probably no different, but you want to make sure that those things don’t cripple your relationship.
People who harbor negative opinions about themselves have a knack for pulling you down with them, and I’ve seen this happen all too often in long-term relationships.
If you ask a woman what she loves about herself and she struggles to find an answer—or even worse, if she makes some self-deprecating joke—it’s probably a warning sign of something much more serious.
If you want to have confidence in your relationship, you and your partner must be confident in who you are.
At the very least, be sure you’re both on the road to becoming more confident.
I’ve seen hundreds of men change their outlook on life by joining my elite coaching program. I know that people can change, and you, just by reading this, probably also believe that. But always be weary of those who think the opposite.
5. Did you hear about [insert topic that is important to you]?
Remember how I said the most important questions to ask are the ones most important to you? Before you ask them, ask yourself if they’re the right questions.
For example, certain men feel they need their partners to share their common interests. Whether you’re into politics, science, sports, or art, if it’s something that you feel deeply passionate about, you may need a romantic partner who shares your convictions.
A friend and his wife spend most of their free time creating independent films. I rarely see them because nine times out of ten, they’re out of town on the weekends, either at a film convention or a festival.
When you look at the two of them, it’s clear that they work so well together because they share the same passion. A shared mutual interest is necessary for some people to make the relationship work.
Oppositely, I have another friend who crafts hunting knives in his free time. His girlfriend has absolutely no interest in what he does. He works on his project for several hours every Saturday while she goes out and gets brunch with her friends. For them, it works.
What you have to do is figure out which camp you fall into.
6. What’s the most important quality you want in a partner?
How would you answer if I asked you who you are? Would you consider yourself to be self-aware? If you had to list your personality traits for me, could you?
Are you outgoing or introverted? Are you generally serious or more of a comedian? Are you a meticulous planner who likes to do things on the fly?
I often see men try to change who they are to be more compatible with the woman they’re dating, but this is just a bad idea, no matter how you cut it.
If you ask her this question and she tells you she likes a guy who can have deep, introspective conversations about the nature of the universe, you better be sure you fit the bill. If not, you’re just setting yourself up for disaster.
While physical attraction is usually the first thing that catches people’s attention, personality helps keep things fresh. If she tells you certain qualities she finds attractive in a partner, and you have none of them, just be honest.
Granted, if she tells you that she appreciates humor in a guy and you recently found a passion for performing improv comedy, that’s fine, but don’t think you can alter your innate personality traits to become funny if you’re not suddenly.
Many men feel like they have certain personality traits that they’d like to get more in touch with but struggle to do so. A coach might be the perfect solution if you’re one of those men.
A men’s coach can help you figure out who you are and how to tap into your innate power and become the best version of yourself.
7. What’s your love language?
You’ve probably heard that people tend to have five unique ways they express affection: words, quality time, physical touch, acts of service, or receiving gifts. Well, do yourself a favor and figure out which resonates with her as soon as possible.
I’ve seen the same scenario play out time after time, where a guy thinks he is the most affectionate boyfriend in the world, yet the girl he is dating doesn’t seem to notice.
Why? It could be because he isn’t using the correct love language. The simplest way to figure out your partner’s love language is to ask her. This one question can help you make informed decisions about so many other things down the line.
If she says she values quality time and Valentine’s Day is right around the corner, instead of taking her out for dinner and buying her a box of candy, think of a more creative activity that she won’t easily forget.
Similarly, if she’s the type that responds to gifts, put some intention into what you’re going to get her. Instead of opting for another piece of jewelry, get her something that resonates with her personality.
Think of it this way: what would you appreciate if you were her?
8. Do you like spontaneous dates?
Or, in other words, “do you like spontaneity in general?” This is a big source of contention for many couples, and it doesn’t always become apparent until some time is spent together.
Certain people need to have everything planned out in advance. They like to have their daily routines, weekend plans, and vacations regimented as far back as possible.
Others find a genuine thrill in being spontaneous. I know a guy who will take a three-week trip to Europe and not book a hotel until he gets off the plane. For him, the fun is in the adventure.
And while this guy has had several serious relationships over the years, every single woman he’s dated has been as spontaneous as he has: the type of woman that will hike the Appalachian trail by themselves.
Understand that things like these are just a matter of preference, but they can tremendously affect a long-term relationship. Not planning things can cause certain people tremendous amounts of anxiety, which can lead to arguments.
9. What would it be if you could change anything about your past?
This is a great question because it will show you how much she ruminates over her past decisions. I find anyone who lives with regret or constantly second-guesses themselves to be completely intolerable.
If you ask your date this question and you get a long-winded answer about her life being one big mistake—about getting the wrong degree, dating the wrong guys, working at the wrong job, etc.—watch out.
If she thinks everything in her life has been a mistake, it may be a sign that she has self-confidence issues there.
A major part of being in a healthy relationship is being happy with who you are, including your successes and failures. If you detect hints of underlying negativity from the woman you’re dating, proceed cautiously.
Negativity is like a disease, and constantly being surrounded by negative people can make an otherwise happy person completely miserable. This is true of your family, friends, or coworkers, especially your romantic partner.
If you feel like you’re struggling to find those strong, grounded people in your life, a support group might be just what you’re looking for. When you join my “band of brothers” and me, you get more than expert life coaching; you get a group that will stand behind you for life.
10. What’s your most valuable possession?
Unless you’re a minimalist who abstains from all material possessions, you probably have certain physical objects you value more than others, and she is likely no different.
A friend who works as a professional novel writer once told me that if his house were on fire, he would only care about his laptop because all his written work was on there. When I asked him about his books (this guy has a home library), he responded that those are all replicable.
It’s a good idea to find her most prized possessions. If she tells you she values her Hermes handbag because it cost her 22 grand, it might be a sign that she’s on the materialistic side.
Just understand that this isn’t necessarily a question from which you want to draw many conclusions. We all treasure certain stuff, and just because you might not personally see the value in something, it doesn’t mean she doesn’t.
For example, many guys love their cars more than their partners. We also like our TVs, sports jerseys, and power tools. To us, they’re valuable, but to her, they might seem completely worthless.
That said, a woman who values a 22-thousand-dollar purse above all other things might not be your ideal partner, so it pays to ask.
11. Do you have a favorite photo?
As the saying goes, a picture is worth a thousand words, and this question will tell you a ton about the girl you’re dating.
If she shows you a selfie she took in a public restroom, that says something about her character and priorities. Oppositely, if she shows you a photo she took in Positano because it was the most beautiful place she’s ever visited, that’s something else entirely.
Does she show you a picture with a certain family member or friend? A picture with her dog? A picture that she isn’t even in?
Aside from what she shows you, pay attention to how she talks about it. If that one photo of the beach in Positano leads to stories about a dozen different countries, she likes to travel.
Casual questions like these are a great way to learn more about her deeper interests.
12. What are your goals in life?
There are two types of people in life: the first group spends their entire day talking about what they want to accomplish; the second group is doing it.
Just by the fact that you are here reading this, you are either already in the second group or on your way to being there, and you want a partner who shares a similarly ambitious attitude.
If you ask her this question, be mindful of how she answers and the language she uses to frame her answer. Be wary of phrases like, “I want to do it, but I can’t find the time…” or “I’m just waiting for the right circumstances to make a move…”
Here’s the brutal, honest truth: you, her, and everyone else you know has the time to accomplish everything you desire right now.
The circumstances will never be quite right for you to get started on your goals, but that’s no excuse for not doing them anyway.
Romantic couples tend to feed off each other’s energy, so you want to either a) be with a partner whose energy aligns with yours or b) have the inner strength not to let anyone stand in your way.
Do you currently possess that inner strength?
Or are you waiting for the right time to find it?
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