Questions To Ask Men On The First Few Dates

The first few dates are ways to get to know each other and determine if the person is worth a relationship. The relationship is not exclusive or serious, nor an interview session. Many woman ask blunt questions that could scare off a man or get an answer that is not honest. The conversations should be organic (not interview-like or a police interrogation) and you should listen intently to what the person is saying as well as observe non-verbal cues. If you ask enough organic questions you will learn so much about the person and their beliefs, values, and how they think. So let’s break down the questions you should ask and why you should ask them. 


1. Are you from here? You may learn that they are in that city because of school, family, or because of a career move. That question can lead to more questions about their schooling, family, or career. If they are from that city, you may learn if they like change, if they would ever leaving their hometown, or like to travel. 

2. So what do you do for a living? You can see what career they chose and why. They may even tell you their passion if the job they have is not their passion. You can see if the guy is good with his hands (if a handyman) or if he is an intellect. 

3. So do you come here to eat often? If the guy takes you to a place to eat, you can learn if it’s his first time eating at the restaurant or if it is a place he goes to often. Maybe it’s his favorite spot, or it was recommended, it could be because its nearby his house or job. This question can be modified if the date is not a restaurant. It could be a museum or horseback riding. Asking why he chose it can give you insight to whether he is adventurous, cultured (likes art or music) or likes to dance.

4. So what made you approach me? Most men are going to say something along the lines of you being attractive, but it can be a lead-in question to what they think of you now after talking a little. You can get insight on how the date is going and if the guy is enjoying conversation with you or if its still just your physical appearance.

5. So what made you order that? Here, you may learn if he has dietary restrictions or if he is a health buff. The price of the food and restaurant or wherever you are can give perception about his finances. It is not always the case, but you can get a sense of how he spends his money even when he is trying to impress you. With that being said, if he takes you to Burger King, it is likely that he is not trying to impress you or does not care to make a great impression. Please note, just because he takes you to a coffee place or somewhere free, it does not always indicate he is cheap or broke. Remember, he is just getting to know you and he may be testing you to see how you act in those situations. Sometimes men test women to see if the woman only cares about money or if they are open to something different.


On the second or third date you may ask about previous relationships or what are his reasons for dating? These next two questions may sound a little like this:

6. So are you just getting back in the dating game? He may say that he just got out of a serious relationship or divorce. He may just say that he is just getting back out there. Sometimes it is best to not bring up the details of the past relationships but stick with the here and now and go from there. The past is the past so you should trying not bringing up your past relationships as well, beyond the fact that you are divorced (not going through a divorced – married is married) or was in a serious relationship. The guy may ask what happened but try not putting the blame on your past mate, yet say things like mistakes were made and you decided to move things forward in a positive direction. 

7. So why are you dating now?/What are you looking for right now? Here, you learn his intentions. Is this guy looking for something fun or does he want a relationship. Is he looking to settle down. If you are not looking for fun then this is your cue to say that you are looking for more than fun. If you want fun but he is alluding that he wants something serious then you can tell him that you are only looking for fun or a friend.  Being honest now can save the heartache later.


It is highly important that in between questions, you see how he speaks to the waiter or staff at the place. You can see if he tips well when paying and if he opened doors or pulled out chairs. Please do not offer to pay on the first few dates unless you can put your money where your mouth is. Do not offer in hopes for him to accept your offer as a test. Men will make a mental note of that. Now expanding on the chivalry, some men did not see chivalry growing up or their past mates did not expect that from them, so do not get all in your feelings if he does not automatically do that with you. Standing at the door waiting for him to open it or waiting near the chair so he may pull it out are ways you can show him those are things you like.


The other questions asked are generally after the guy responds to your initial question above. Then you can get insight into his work ethic, family values, and belief (if he is religious). These questions should appear natural and inserted in normal conversation and not in a row like you are checking off a list.  In fact, those questions can be asked over the course of three dates. Those questions are not all-inclusive, but they can help you determine if this guy is worth another date, but stay clear of political or social debates early on. Give it a try. If you need more help on how to be conversational then book a session with me at for coaching.

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