Dating Advice For Women: Questions To Ask Men


“A date isn’t an interview or a confessional. You’re being judged on the things you say and do during a date. Leave a first good impression and your chances for a second date are much higher.” Blaine Barrington, Dating and Relationship Coach

When it comes to dating advice for women, one of the first questions many women ask is what questions should I ask?

It’s a great question because when you’re getting to know someone who you’re interested in for a relationship it’s common to ask questions.

This is especially true with online dating where it’s easier to ask questions and not feel that you’re pressing too hard to get to the answers that are important to you.

But it can be a trap if you’re not careful. The questions you ask and the answers you give can turn a guy off.

Keep in mind that when you meet someone – online or offline – and you want to know something about them you don’t want to make it look like it’s an interview.

So you don’t ask things like, “What are your goals?” Or, “Where do you see yourself in 5 year’s time?” Or, “What are your strengths and weaknesses?”

Those aren’t the types of questions you ask – although some of that information may come about through casual conversation.

For example, he tells you what he does for a living. And then he says that in five year’s time he expects to be promoted to a higher position or move on to another job.

Instead of these “interview” type of questions, ask another type of question.

These are what I call initial “qualifiers” to see if it’s worthwhile moving forward with the guy you’re interested in.

Common questions from women – whether you’re on a date or you’re on an online dating site – can include the following:

1. Have You Ever Been Married?

These days “single” can mean never been married or divorced and no more ex in his life.

With online dating you’ll usually find a section about marital status.

Some guys have been married and divorced. Some men are widowers. Some are separated from their wife.

Others are married and looking for an affair or a no strings attached arrangement.

And others have never been married. They may be confirmed bachelors, they may be players, they may be smooth talkers, or they may not have found the woman they’re searching for.

2. Are You Seeing Anyone Right Now? [or] Do You Believe In Monogamy?

This question is sometimes disguised to mean whether he’s sleeping with anyone or whether he has a relationship with someone that he hasn’t disclosed.

This is a particularly important question since most people want to have an exclusive relationship.

With sexual disease prevalent, it’s not unusual to expect exclusivity in a relationship – especially if you’re intimate with a man.

If you ask, “Do you believe in monogamy?” it could reveal whether he’s sleeping with other women or wants to date a number of women instead of just one exclusively.

3. What Do You Do For A Living?

It’s common to ask this question. In fact, it’s probably one of the most frequently asked questions. The man you have your eye on may be a professional. He may be unemployed. He may be “between jobs.” He may be an entrepreneur. Or he may be underemployed or unemployable because of his age or for health reasons.

It will be up to you to decide which is acceptable to you. Some women don’t mind helping their man financially. Others have done it all their lives and are now looking for more security from a man who has a good job.

These days with housing and living costs so high, it’s nice to know that the man you’re dating has either a good job or has some financial resources to fall back on if the relationship progresses and especially if you decide to get married.

4. Tell Me About Your Family – Your Parent, Your Siblings, Your Children

We all like to know something about the other person’s family. After all, if things were to progress, you would eventually meet his family.

It’s also nice to know something about his relationship with his family. For example, is he close to his parents and his children.

If he’s an older man, it’s likely that his children are grown up and on their own. And sometimes that can be important in a budding relationship.

Some people like children but don’t want to raise any more children. So that could be a deal breaker for them when considering dating a man.

5. What Do You Like To Do For Fun?

This question will give you an idea about whether the guy you’re interested in is a fun guy. Whether he likes to travel. And whether the two of you have common interests.

It’s also interesting to know something about his passions, interests, hobbies, and how he spends his free time because it can open up new opportunities for things to do together.

Of course, if he’s into hang gliding or rock climbing or base jumping or bungy jumping or skydiving, he might be a little too adventurous for you.

Even worse, he might encourage you to take up extreme sports when you’re deathly afraid of them and prefer to have your feet firmly planted on the ground.

6. How Long Have You Lived In Your Town or City?

People move. And sometimes you’ll find a common town or city where you have both lived. Or you may have mutual friends from the same town or city.

It’s always easier to relate to someone if you have something in common or a shared experience.

7. Do You Drink, Smoke, Gamble, Or Use Non-Prescription and Prescription Drugs?

In other words, what sins do you like?

You don’t have to ask this question outright. For example, you could ask, “Have you ever been to Vegas?” or “Have you tried (name a casino)?”

In most cases, you’ll get some idea about a person’s “sins” on the first date or two. For example, he may order a lot of drinks if you’re at a restaurant. Or he might reveal his favorite pastime is getting together with the guys and drinking. Or he may excuse himself to go outside for a quick smoke.

Most online dating sites have a section for this so you can see what a man’s habits are.

And if you’re looking for someone who doesn’t smoke or do drugs and is a light drinker then it’s important that you know right from the beginning so you can qualify or disqualify him as a potential romantic candidate.

Drugs can be a major issue – and a deal breaker – for many people.

Even prescription drugs can be a red flag since they can affect a person’s behavior and even their sexual performance.

8. What Are You Looking For In A Partner?

This is a great question to ask any man you’re interested in because it gives you an idea what his expectations are.

He might, for example, be looking for casual dating. Or a one-night stand. Or a friend with benefits.

He may be looking for a companion for social outings and travel. He might be looking for someone to talk to and do things with as an activity partner.

Or he might be looking for love and a long term relationship with the possibility of marriage if things work out.

Some guys might also tell you they’re not interested in raising any more children – especially if their own children are grown up. So, if you’re a single parent with young children, he probably isn’t a candidate for a relationship.

If he asks you the same question, it’s best to be candid about what you’re really looking for so as not to lead him on.

But you have to be careful how you answer. For example, if you say you’re looking for a husband it will very likely scare him off.

It’s best to keep it general in the beginning. Instead, you might say you’re looking for someone to enjoy fun times with and see if a relationship develops.

Of course, if you’re only looking for intimacy then it’s best to disclose that right at the beginning and say you’re looking for a lover or for a no strings attached arrangement.

If you’re only looking for a friend or companion then he may not be a good choice if he’s looking for a lover or a future wife.

Avoid the type of answer like “an honest man” or “a guy who isn’t a loser” or “a nice guy.” These types of answers can signal bitterness from previous bad experiences with men and can reflect poorly on you.

When asking questions you don’t want to appear as though you’re prying or trying to complete a man-catching checklist.

You want to keep things casual and light.

The trouble is that when you’re considering dating a guy, you want to know that your time is well invested and you don’t want any surprises that could be deal breakers.

On the other hand, you don’t want to turn the guy off with your probing questions.

Of course, the tables can be turned on you as the man asks you questions.

Questions like:

1. What Happened In Your Marriage?

This is a question that could still cause you pain or anger if you’re recently divorced and starting all over after many years of what you thought was a happy marriage until your ex-husband ran off with a younger woman.

And it’s up to you whether you want to go into the details. If your ex husband was a cheater or had an affair or multiple affairs it’s entirely appropriate to mention that. Or you can simply say you and your ex-husband grew apart or you fell out of love and only stayed together until the children were grown up.

2. How Old Are You?

Many online dating sites ask you to indicate your age. Most people are reasonably honest about this question.

Some women are embarrassed to think that they’re looking for a relationship in their later years when their dream was to be married all their lives to one man.

It used to be that a man would never ask a woman’s age.

But times have changed.

It’s your choice whether to tell him specifically how old you are.

If the relationship progresses he’ll want to at least know when your birthday is. Or he might allude to how old you are by making remarks about specific events in history – for example, when the Beatles came to America.

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3. How Many Relationships Have You Had In The Past?

This is a cute way of asking how many men you’ve slept with.

It might even give him an idea of your experience as a sexual partner.

It’s not a question you need to answer or divulge.

It’s your personal business.

4. What Would You Do If You Found Out You Were Pregnant?

This is an oblique way of asking whether you’re sexually active and whether you use birth control.

It’s a question that eventually has to be answered if you’re intimate with the man you’re dating.

But as an initial question from someone you don’t know very well it’s up to you whether you answer it.

5. Do You Enjoy Sex?

For a lot of women sex questions are a turn off until they get to know a guy and think there is a connection.

Be prepared for this question from guys. Because, let’s face it, most guys are interested in sex in a relationship.

But use your common sense, too. It’s not a topic that should be encouraged in the beginning. If the question is asked in the first email or two – and you don’t know each other very well – then it’s inappropriate.

You should get to know each other first before delving into the “sex” questions which will include things like preferences, forbidden practices, birth control, condoms, sexually transmitted diseases, and being tested.

6. How Would Your Friends Describe You or What Would They Say About You?

It’s another great question. Generally you want to be able to bring out your good points about your personality and qualities.

It’s a tricky question because he might be looking for the negative qualities you have – you might get angry quickly or you might be a critical person. Or you might be jealous or you might be needy or desperate.

These qualities are guy turnoffs. And, in a guy, they’re very likely turnoffs for you too.

Obviously you want to put your best foot forward when answering questions from a prospective relationship candidate.

You want to keep things upbeat and positive. You don’t want your potential lover to wince and duck his head at the thought of being savagely mauled by your overprotective Chihuahua or the thought of the front door being smashed open by a jealous ex husband or boyfriend as your new lover has you in his arms making mad passionate love to you.

The thing to keep in mind with asking questions is that the answers to many of them will come as you get to know the man you’re interested in.

And be prepared for the answers you ask be asked of you.

Find The Man of Your Dreams Who Makes You Happy

Just as there are questions to avoid asking, there are also topics to avoid talking about.

In the Girl Gets Great Guy System – which is dating advice for women who want to find the man of their dreams – I not only show you how to ask questions without it seeming like he’s applying for a “position” in a job, I also cover 15 different topics to avoid discussing on the first date because they can change the mood and instantly turn guys off.

The Girl Gets Great Guy System is for the woman who wants to find her one true love. It’s for the woman who:

– Is longing for a loving relationship
– Never seems to be able to keep a good man for long
– Always seems to pick losers and deadbeats
– Wants to have more dates with quality men

Click the following link to find out more about the Girl Gets Great Guy System

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