Dating Advice

Best Questions To Ask A Potential Love Interest


If you’re just looking for casual questions to ask someone on a first date, go here.

If you want to know what to say when you approach a girl for the first time, go here.

(Below are more serious questions)

After you meet a girl/guy and while you are establishing a friendship, you should get answers to these questions before you start dating. These important questions beg for an answer. They reveal a lot about what that person expects, and what that person is looking for in terms of their dreams, their spouse, their leisure time, and their ideals.

1. In an ideal relationship, what would you spend the majority of your time doing?

You need to be with someone who you would actually hang out with, someone who enjoys the same things as you. Yes, you can share each other’s different interests, but that’s why you need to ask this question, to see if you would enjoy adapting to their interests or if they would enjoy adapting to yours.

2. What do you expect from a guy/girl you’re dating? or What do you expect from a man/woman in your life?

You’d be surprised with the answers to this question. As humans, we assume that people have the same expectations that we do. Unfortunately, men and women are wired differently. That’s why this question is important. Not only are we different because of our genders, but we’re different because each person’s past experience helps mold their expectations and each person’s past experience is different.

3. What is your idea of living a good life?

Here you get a taste of what motivates the other person. You’ll get a taste of what drives them, what gives their life meaning and significance. It also gives you a view of what a future would look like with them.

4. What does a good relationship look like?

It’s always nice to know what the other person views as ideal in their eyes. You can see if you’re looking for the same thing in terms of what makes a relationship good.

5. What are you looking for in a guy/girl?

Let them name the top three qualities that are non-negotiable.

6. What have you learned from your past relationships?

Ideally, it would be nice to go through each of your past relationships, not to relive pain or point out the mistakes of your exes, but it’s important to know that the person you’re with has learned from their own mistakes and isn’t just moving forward ready to make the same repeat mistakes with you.


Give the person time to think about these questions. They need thought. Most of them can’t be answered right away. These are deep questions that could lead to lengthy conversations, but it’s important to know what you’re getting into.

Failed expectations are what causes a lot of disappointment. If you know what the other person expects and desires from the onset, you know if you’re able and/or willing to meet the other person’s needs and wants.

It beats questions like, “What’s your favorite color?” In the scheme of things, questions like that don’t matter. You also need to know about how the other person feels about kids, (yes, no, number, who raises them) lifestyle locations, (city, suburbs, country, nomad) marriage, (soon, later, never) religion, (same, different, important, not important) family, (close, absent, involved) recreation, (outdoorsy, night life, traveler, sporty…)

Those things can be discovered when you’re dating already. Some other ways to find out more about the person you’re dating is to take a Myers Briggs personality test, the Strengths Test in Now Discover Your Strengths or go to or and create a fictional profile, answering all the questions together.

Relationships are work. It’s always going to be challenging to try to love someone who’s different, but the more information you have, the more prepared you’ll be.

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Article written by:

I love thinking about the intricacies of dating, love and life. I share my tiny lessons in the hope that it helps you as you navigate the dating world.

Join the discussion

  1. Dont Date Guy

    Most people couldn’t tell the answers to 80% of these questions even if their life was depending on it. I pulled this trick couple of times on a date and it ended up in a disaster.

  2. BrianJ

    Wow… I’m going to have to disagree with some of the advice you’re giving guys. Don’t get me wrong, it’s cute advice… but it’s not practical.

    Emotions are not a choice… that includes attraction. A guy can’t help who he is attracted to. On the other hand… chicks can’t help who they are attracted to either.

    No amout of “common sense” or “rational” you try to put behind it… you will never be able to “talk” your emotions out of the way that they do.

    Again… cute advice… but impractical…

  3. Lee Coles

    Sound advice- gets beyond career and taste and into values.

  4. Lindsey

    I would have to agree with about 99% of the information here. To love someone (who they really are) is a daily choice. Yes, you can’t help who you are attracted to or love, but you can’t really fall in love with someone if you don’t know the answers to the above questions. If more people new the answers to the above questions, they would either not be married or would not get divorced. But then again, some people don’t want to go deep. And marriage is not for everyone.

  5. Michael

    This information is a accurate as it gets. I used this on my current girlfriend before we started dating and well…we are dating so it worked. Answers don’t come fast but they will come and this set of questions is simply perfect.
    Very practical, it works like a charm…

  6. Corey

    Good day I just wanted to ask you all stop through at

  7. Jeanie Gulan

    The style of writing is quite familiar .
    Have you written guest posts for other blogs? I mean really truthful for me

  8. Roni Martha

    Insightful page, very helpful, good website as well, so appreciate it, will bookmark.

  9. Tracey E. Bennett

    I agree that failed expectations cause disappointment. That’s a good reason to be yourself and not try to fit into somebody else’s idea of a good partner.

    Readers might enjoy this article: “Good Conversation Starters: 3 Sure-Fire Tips to Flirt Successfully and Break the Ice with Women or Men.” Go to

  10. Alanna Crittenden

    Hi, your site completely makes me think of a great website I saw on how to get pregnant fast.

  11. Madison

    My 2011 might be greater with this idea!

  12. Heather

    I think about another good question on first date
    What do you prefer to have together? a baby boy or a baby girl????
    If he still did not run… so I recommend you check with him this amazing site which teaches how to choose the sex of the newborn

    Good luck


    This is interesting advice.. while these questions are very good and useful, i would add that the timing of the questions is important also.. You don’t wanna scare the other party away..

  14. Laura

    To someone who said that most of those question could’nt be answered I can say that maybe that was the wrong person you asked all that then 🙂 everyone who has some common sence and thinks a little bit could answer that. And if he/she cant do that, then well…. in that case I think I would have my answer if that person is worth my attention 🙂

  15. MidoriLei

    Laura, so true. The kind of person who is willing to invest some thought and provide you with answers shows that he is more serious and thinking more long term than the person who can’t answer them or doesn’t want to. It’s not that they can’t be answered. It’s that some people aren’t willing to answer them. It also shows that the person actually cares about relationships and how to make them work.

  16. Rahul

    So J prom is coming up and I really want to ask this girl. Shes been a friend for the last 4 years, but shes been going out with one of my friends for the last 1-1.5ish, its just that they have broken up at the mo and no one knows if they are gonna get back together. But since they have done that like 3 times already, idk what will happen. But anyway, Idk what I should do. I don’t wanna offend my friend (the guy). I asked da gall what her plans were for J prom and she was like, I’d go if someone asked me. I wanted to do it right there and then but I controlled my self lol. What should I do??

  17. MidoriLei

    Rahul, ASK HER! her comment was a hint to ask her! But if you don’t want to offend your guy friend, run it by him and let him know your plans to ask her out. Don’t ask him for permission (as she does not belong to him and they are broken up) but just let him know your plans so he isn’t shocked when you go together. If he is like “That’s not cool! Don’t ask her to the prom!” then you have to say, “Sorry, she’s a free woman, she’s going to have to make that decision.”

  18. dede

    lady and sports woman very romantic and worker…serious ..

  19. AS

    The questions are relevant & important but not sure if the other person would run the other way if you asked these questions to early on and particularly if you’ve only been a couple of dates. It may seem like you are getting too serious, too quickly. I think at some level you do start getting indications of answers to these questions naturally, in general conversation. So for example:

    1. In an ideal relationship, what would you spend the majority of your time doing?

    When you are asking someone what their interests are, how was their week etc and of course how available is this person to meet with you – you start getting an idea if he has time and space in his life for a relationship… Without actually having to ask the question directly.

  20. MidoriLei

    AS, i love the way you sneak it in a normal conversation! I do agree with that wholeheartedly!

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  22. NickZ

    1, 2, and 5 are the same question worded in three different girly ways.

  23. Susan Silverstone

    Hey Datingadvicefromagirl,
    In addition to your post I was wondering, Many people have questions related to their love life. Some go through tough time with their partner whereas some find it very difficult to find a life partner. Problems related to love life can make it very difficult for you to concentrate on your personal and professional life. That is the reason why many people to make use of free tarot reading and free psychic online to know how to deal with their love life.
    Keep up the good work

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  25. Myron

    Back when I did my mountain ops training, I once accidentally knocked my helmet off a cliff. I dove for it and caught it before it went over a sheer drop. To my credit I caught it. To my detriment I almost fell off a goddamn cliff to save a helmet.

  26. SEO

    Hi There

    I think, its not just the answers that count, what counts the most is, if he just knows, what he/she is looking out of you, is clear, straight forward and honest


  27. Issabell Ryder

    So idk if my friend just likes me as just that or as a could be more! He tOok me to prom and we had a great time but now when we hang out it seems like there could be more to it! But we r never alOne and when we get talking and have a moment it gets interupted! The worst part is he’s going to college next year and I will only get to see him on holidays! Wut do I do!?!?

    • MidoriLei

      Issabell Ryder,

      He needs a little help if he likes you. But not too much help:) Tell him you’ll miss him when he goes off to college. See if he takes it from there. You only want to give “hints” that you’re interested, not outright tell him. Let him muster up the courage to tell you first. Give him a chance to man up… but help him out a little by giving SUBTLE hints that something could possibly be there for you. Does that make sense? Do you need more examples?

  28. Issabell Ryder

    Yes it makes sence and thanx for helping! 🙂 but a few examples wouldn’t hurt…how do u subtletly hint and not seem like u r waiting for something or seem like u r hiding something? Plus he is a really shy kid! He is sorta breaking out of his shell a little now, but even his mom told me he is more himself with me than with most people. And r families r going on a trip together and I’m having a hard time deciding if I really like him or if it’s just because he is leaving! On the last day of school we signed each others year books just like every year but this time it want just a signature, I told him I was going to miss him while he was gone and that I had fun at prom. We switched back and i read his and it said pretty much the same thing. Is this just a friendly relationship or does it have a little bit of potential?

    • MidoriLei

      Issabell Ryder,

      I think before you give any subtle hints, you should first make sure you really like him romantically and not just as a friend, otherwise you’re going to be wasting your time and leading him on. Guys only like a “tease” if there’s hope that it can be more. If it’s just a tease just to be a tease, it’s frustrating.

      How do you know if you like him more than just a friend? Does the thought of kissing him make you happy or does it feel neutral or even gross? Do you find yourself wanting to not just be around him, but do you find yourself wanting to be close to him, and does the idea of his affection or even a touch of your arm give you shivers in a good way? Those are a few questions you can ask yourself.

      Once you figure out that, and if you realize you DO like him more than a friend, there are ways to hint that he should “make the first move.” yes, he may be shy, but don’t let him get away with having to make the first move just because he’s shy. He needs to man up just like every other guy.

      You could be bold and ask him, “Has the thought of kissing me ever crossed your mind?” Wait for his answer. See, this looks like you’re making the first move, but in actuality, you’re not telling him you’ve thought about it. You’re just trying to tease him with the idea and see if he’ll use the opportunity to make a bold move, like actually kiss you.

      Worst case scenario, if he says, “no,” just play along with it, “Oh, come on:) So you really think it’s possible for guys and girls to ‘just be friends?'” This way you don’t take it as a “rejection,” because it isn’t a rejection. I mean you are friends, it’s just asking his opinion. Throwing it out there like that will show your confidence but also give you a chance to give him an “in.”

      If he says, “Yes, I have thought of it,” Put him in the limelight and make him squirm a little. Ask him, “Like, have you thought about it once? or like, periodically? or like it keeps you up at night?” and smile teasingly.

      And if he’s like, “Why do you ask?” or if he’s like, “Have you thought about it?” Tell him, “I’m the one doing the questions here Mr.” or “Don’t turn this around on me!” Then pause for a second and tell him, “All I can say is, I wouldn’t be completely opposed to it.” Then smile and completely change the subject. “Hey, wanna go get some ice cream?”

      Issabell, I guess that was ONE pretty big, comprehensive example instead of a couple of little examples:) Good luck!

  29. Issabell Ryder

    Thanx so much! It helps a lot! 🙂

    • MidoriLei

      Issabell Ryder,

      You’re welcome! I would make sure to read the latest article as I added some stuff that was not in the comment response:)

  30. Anonymous

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    you make blogging look easy. The overall look of your site is great, as well as the content!

  31. Independent Girl

    How can I find the guy who loves me more than his life? If he comes in front of me then how can I find a loyal man in him.

    • MidoriLei

      Independent Girl,

      Good question. You can find a guy who loves you more than his own life if he’s willing to wait for marriage to have sex. You’ll find a guy who loves you more than he loves his own life if he believes in God and fears and respects him. God is love, and if you find a man who not only knows and believes in God, but actually takes him SERIOUSLY, then you’re at a good starting point. You can tell if he is a loyal person by seeing how he treats people. Does he only do kind things to get something in return? Then he does things for his own gain. Does he do the right thing when nobody is looking? Does he do the right thing even if he doesn’t get credit? Is he honest? Is he sincere even about the smallest things? Is he more concerned with making things more convenient for others or for himself? Does he live two different lives or is he the same with everyone? Do others respect him? Does he have any secrets?

      These are all questions to help you find your answer.

  32. Lisa Shield

    I would probably start with just one of these questions and work up to some of the others. Don’t ask them all on the first date. You’ll send him running for the hills.

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  36. Jerry

    Hi, I met this woman online she live in louiaiana and I live in Cali. She told me at first that she did want talk and waste her phone time with someone that live far. I understand that point. So I said let just be friends so I go online I send her a message but, she want respond for like two day or so I know that she got the message. I really like her I think she is very sweet so I would like to meet. I want to know how to go about getting her be mine. Louisiana women or very hard to understand they don’t smile they that they give out the wrong message to men.

    • MidoriLei


      Tell her that love knows no distance and that you find her very intriguing and would even be willing to make the trip to meet her. (only if that’s true.) If you wouldn’t be willing, then she is right, she would be wasting her time. Good luck!

  37. Lovecounselor

    You pose an interesting Dilemma, you claim by asking these questions you have a better understanding of the guy or girl you want, the point is someone is attracted to someone, but Love depends on many variables you dont even list, the list of questions you want someone to ask are not infallible tools, Human beings react to different cues when in Love. To expect these questions to rule over time is impractical, No one goes into a relationship knowing all about the person. I have a Love interest now but he cant even bring himself to ask for a date, not even for Lunch or a coffee break. Some people are attracted in a sexual, some byother methods. If you truly want to know something asking wont help. The old adage is Women want to hear and Men are willing to say it just to get what they want. It goes for both sexes , only time will tell if a Man or Women truly loves you. It wont be just what they say but what they do to show it too, Your actions as well as your words need to say the same thing…Happy Dating. The advice I give comes from years of experience about Men and Women in Relationships.

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