28 Good Questions To Ask On The First Date To Determine If He’ll Get A Second

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I am going to get into good questions to ask on the first date.  Knowing what questions to ask a guy on the first date is probably the MOST important tip I can give you. Mainly so that you do not end up wasting your time going on a second date or continuing to see someone for weeks, months, or even years only to find out that they are a complete psychopath or someone you do not want to be with.

A good practice in dating, is that you want to know the important stuff about a man upfront.  But there is a art to asking good questions because you do not want to look like an FBI agent interrogating someone like they committed a crime. This is why these are good questions to ask on the first date beacause you want the conversation to flow naturally, to have fun on the date, and actually get to know one another without it being awkward or pissing him off because he thinks that you are being way too noisy.  Also check out my video down below on how to weed a man out on the first date and don’t forget to subscribe to my YouTube channel. 

As I learned from my one week on Tinder, because we are so consumed in social media, technology, and we have removed ourselves from actual face to face social interactions, so many men have found themselves being socially awkward around women and have actually lost the art of having a conversation or even knowing how to date women. Instead, dates and conversation has been replaced by sexual innuendos, Netflix and chill, and asking what color underwear you are wearing.

Understand the best tips for a first date is that you control the tone of things, the conversation, and do not let things go south. Through your questions and your conversation you want to let him know that you are an intelligent high value chick that requires him to actually put in some effort in getting to know you and that you require having an exchange of words (AKA a conversation) so that you can determine if he is worth your time. Of course don’t say it to him like that exactly, but the way you speak, the questions you ask, and the way you carry yourself should say that about you. So here are good questions to ask on the first date

1. Good Questions To Ask On The First Date ~ What Do You Do?

Some of the good questions to ask on the first date is what a man does. You want to know if he has a job, if he is in between jobs, if he sells drugs, or if he works for the mafia.  Although, it sounds crazy I have had a man lie about his job.  He told me he was a principal at a special needs school.  The crazy thing about this is that I had interview for a mental health position at the same school a few months back, with the principal, that was not him.

So of course I knew he was lying. Which is why it is important to ask the question AND follow up questions because any man can tell you anything about what they do and that does not make it true. But if you follow up with more questions it makes is harder to just lie about it.

If a man is a loser, has no motivation, no job, or is working a dead in job then it is best to know that up front so you can determine if that is what you want to deal with (which I talk about in the video below). I personally think that a man does not work does not eat but if you want a man that is not really doing anything with his life career wise and has no long term goals then that is on you. But it is a good idea to at least know that up front.

Now, even if you ask a man what he does just do not stop there. Remember that this a conversation. Take the guy above where I knew that he was lying about being a principal. I did not accuse him of lying, I just asked follow up questions. “Oh how long have you been doing that?” “Do you like that you do?” “And how did you become principal?” In which case he got tripped up because of course what he was saying was a lie.

Notice that I did not say “You’re lying I had an interview there a month ago.” It was just a fluid conversation, and based on his answers I could tell he was not being truthful because he had to think of things to say to answer my questions. I did eventually tell him that I had an interview there, and his face was priceless.

3.-9. Good Questions To Ask On The First Date ~ Appropriate Follow Up questions:

Here are some good questions to ask on the first date follow up questions to the above question instead of just asking what he does and changing the conversation abruptly.

3.  Do you like what you do? 

4. What made you get into that? 

5. How long have you been doing that? 

6. Do you want to work there forever or do you want to branch out and do something else? 

7. Did you have to go to school or get a degree to do that? 

8. How long have you been working in the field? 

9. That is an interesting job, I have never heard of it so what do you do from day to day?  (If someone has a uncommon title that you have never heard of a day in your life this is a great question to ask.)

Since this is all about determining if a man is worth your time pay attention to his answers to see if that is something you can deal with. If a man says, “my job requires me to move out of the country next month.” Then of course you may not want to be in a relationship. If a man says “I have to travel 28 days out of the month to other cities” then that may not be a deal breaker for you but you need to really think about if that is something you want to do.

Also, this is a chance to look at how ambitious the guy is and if he is goal oriented. Another true story is that once I dated a barber.  There is nothing wrong with barbers he did not have any health insurance despite having health issues, he did not have a plan of what he wanted out of life for the future (i.e starting his own business, his own shop, or what) he was perfectly fine being a barber for the rest of his life.

For you that may be fine, for me not so much. I really wanted a man who was goal oriented and career oriented, and once that does not like to stay in the same place but always wants to do something new, since that is how I am. I can imagine getting frustrated with someone who was just content with where they were and really had no plan to move up in their career, ever. But you may be difference.

My point is that good questions to ask on the first date are one that have a point.  The whole purpose of dating questions is to determine if this is someone you want to continue dating, so if they tell you that they do not have a job or lack direction in their life as a whole you know that up front.  And more than likely if they lack direction in their career and in there own life then he would not be able have a clear direction when it comes to an actual relationship or being with a woman on a serious level.  Also check out my video down below on how to date as an ambitious woman and red flags to look for.

10. Good Questions To Ask On The First Date ~  Do you have children?

Having children can be a deal breaker for some people, so it is better to know if they have children up front and this would also be a good time to tell them if you have children; because that could be a deal breaker for them. True story, I once went out on a date with a man and I simply asked him how many kids he had. This one went down in history as one of my bad dating stories in which he stated that he had like 7 kids by seven different women.

Of course I did not freak out but I did say to myself that I was not going to go out on a date with him any more because for me that was way too much baggage. Now imagine if I had not ask that questions for many dates in or until my feelings were deeper. I would have been very disappointed and probably had a more difficult time cutting him off. But since I  barely knew him and this was just our first date it was super easy.

11.-14. Good Questions To Ask On The First Date Follow Up Questions

11. How many children do you have? (because as we see from above he can have kids but there is a difference between two kids and seven). 

12. How old are they? Also having a 10 year old child is not the same as having a 2 week old child.  A two-week-old child is young, his focus should be on a new born baby not finding another woman.

13. How often do you see your kids?  A huge red flag is if a man has kids that he does not see or does not take care of.  This is a character flaw. If a man does not take care of his own flesh and blood how can he take care of a woman in a relationship. And why would you want a man that is a bad father anyway?

14. Do your kids live with you?  It will help you know where you would fit into his life if you continue dating.  It is good to know that if his children live with him then if you get serious you would probably have more contact with the children then a man whose child does not live with him or lives out of state. Heck, it would even be good to know if he is a single dad and the mother of his children is a drug addict who loss custody of their kids and now he has a retraining order against her. I mean that is probably not going to happen. But you never know. 

15. Good Questions To Ask On The First Date ~  What Do You Want out of Life?

Goals can change over time, questions about their goals are still good questions to ask on the first date. It will tell you if they are a planner or if they have flying by the seat of their pants. It may even tell you where you fit into the equation.  If a man tells you that within a 1 year, he wants to go back packing around Europe for a year before settling down.  There is nothing wrong with that, but it may also mean that it does not want a serious relationship.

If he says that he wants to be a preacher and have his own church, you need to determine if that is what you want.  If he says “I don’t know” or “I don’t care.”  For me personally that is a turn off because it shows a man lacks assertiveness. As always it is great to ask follow up questions. I once dated a guy who said that he wanted to own a business and buy a home but he really had no real plans on how to get there.

It would just a bunch of wishing and hoping. I can say all day everyday that I want a million dollars but if I do not know where it is coming from or how I will get it, it does not really matter what I want does it?  What I want is not going to become a reality because I don’t have an intention to make it reality.

16. – 20. Good Questions To Ask On The First Date ~ Here are some great follow up questions:

16. Oh okay, that’s cool so how do you plan on making that happen? 

17. That’s a really big goal when do you think that you would reach it? 

18. So is that something that you’re into now? 

19. So what have you done so far to make that happen for yourself? 

20. That is an ambitious goal, how do you see yourself getting there? 

Most of these questions come from a place of being curious in which case he should be happy to answer them. Which is why they make good questions to ask on the first date. If your questions are attacking like telling him his goals are dumb, that he is not doing anything to get to his goal, or that he is wishing upon a star then that is just mean.

Even if that is the case you do not need to verbalize it, don’t make the date awkward. Just listen to his response and the more comfortable he is talking to you the more he will reveal and after the date if you are not feeling what he is saying then you can just make up your mind to stop dating him.

21. Good Questions To Ask On The First Date ~ Getting To Know Things That You NEED to know without it being awkward.

As a Christian myself, I personally want someone who is also Christian. I also know that downright bringing up religion can be super awkward and cause a religious debate if you are too forceful. So for me finding out your religion or if you are a worshiper or Satan is important. And here is how you can bring that up if a man’s religion is important to you.

22. If they have a cross on around their neck or something just say : “Or I love that cross, are you religious? “

23. Do you have plans for Easter (or some other religious holiday) as most people who are Christian go to church on this day. 

24. I gave up xy and z for lent? Do you practice lent? 

25. I grew up in such a spiritual and/or religious household so a lot of that sticks with me, what about you? 

26. On Sunday I have to go to church or (Wed I have to go to Bible study) or ( I really love to volunteer at my church for xyz) what about you?

27. The other day I was watching Joyce Meyer, or Joel Osteen and she spoke about the importance of having goals (or some other general none religious statement) have you ever watched her? Seeing as how both of these people are Christian speakers that are popular if he is Christian then he probably heard of them.

28. I read this interesting book (name a religious book) have you ever heard or read it? 

These are good questions to ask on the first date specifically regarding religion (if that is important to you) that will open up a conversation and allow you to find out what you need to know. Also, check out my video down below on the dangers of picking someone unequally yoked so that you can truly understand how important this process is.

Questions to NOT ask on the first date

Now that you see the good questions to ask on the first date, here are some questions and behaviors that you should not do on the first date.

  • Politics: Just don’t do it. People are so sensitive about politics in this day and age that it can start an argument or it can take up your ENTIRE date going back and forth to the point that you are not able to get to the real questions to ask the guy that matter (such as the ones from above) because you are stuck talking about politics.
  • Their Ex: I know it is tempting to be noisy and you may want to know but the first date is NOT the time to ask about that. Don’t ask about the ex, when they broke up, how they broke up, or what went wrong.  If you continue to date then all that stuff will come out in the wash but a first date is not the right place to discuss that.
  • If they are dating anyone else: You are going on a first date, it is safe to assume that because they do not really know you, they are dating someone else.  And you cannot get mad about it there is a different between dating and a relationship (click here to read my blog on that topic). 

However, if you ask them and they say yes, then you are going to ask how many, when was the last date, is he sleeping with any of them, and how long he has been dating them? It has the potential to go left and cause you to be upset for no reason because you two are not together and this is your first date. It also has the potential to make your date about all these other women when really it is about you two.

  • Sex: Do not talk about sex, do not have sex, and do not talk about how many people you had sex with. Do not ask them how many people they have had sex with, if they like sex, what is their favorite sexual position, or when was the last time they had sex.  Sex should not come out of your mouth at ALL. And any type of sex conversation that he tries to initiate should be ignored and disregarded in a polite way.  You can also check out my video below to see these behaviors actually play out on a date. 

So depending on how you date you may or may not be thinking that these questions are too much. If you just want to date for fun with no strings attached then by all means do you. But these are for women who have no time to waste in figuring out if this man is even worth their time and if he can add value to her life if they were to get into a relationship. As I said in my book for single women (which you can click here to buy).

"Being equally yoked means there is a relationship between two people that have similar things to offer each other and balance each other out."

What this means is that you need to start getting to know if a man is someone who is equally yoked with you and can add value to your life as soon as possible. If your goal is to have a relationship, have a serious boyfriend, or to get married then having a good partner to build with is important to identify.

If you know a woman who is out there dating then don’t let her waste her time. Share this post with her to help her out.  If you want to get the first chapter of my Single Women’s book “Fix It, Jesus! For Single Women Only. The Straightforward No-Nonsense Guide To Dating, Relationships, and Self Improvement” for free then just click here or the picture below and it is yours.

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