Dating and Relationships: 20 Questions to know by the 3rd Date!

When I was around 19 or 20, I dated a guy for weeks without ever knowing his home phone number or even where he lived.  Whenever we’d go out, he’d drive us about an hour away, to the major city nearby—which I looked at as both exciting and fun.  That was until the day his live in woman/common-law wife came knocking on my door, to confront me about who she claimed was “her man”!  She wanted to know how I could’ve been so dumb, as to not inquire about his relational state– which I admittedly was, but this phenomenon is not as uncommon as one might think.

I’ve met numerous people over the years, who just like me, have gotten into full fledged relation (or situation) ships with people they barely even knew: women who’ve gotten entangled with married men living double lives– men who’ve slept with women not even knowing their full name.  And these weren’t young people either; unlike me and my high school and college counterparts, who partook during the time when we were expected to be young and dumb, I’ve witnessed this from individuals who were way past an age that demands they should know better!

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I wonder then, what is their excuse?  Why would a single person of mature age (30+), fail to do their homework when vetting a potential mate, when it so often leads to such disastrous results?  Maybe it’s ignorance, or desperation, or simply lack of foresight– whatever the reason, it’s a behavior that must be addressed!

pexels-photo-1181698Asking the right questions– in some cases casually and in others, directly– can assure you don’t waste time on the wrong people.  This is not to suggest that you should sequester potential mates and interrogate them like a detective, it simply means we should approach each with a blueprint.  This includes knowing exactly what we want in another person, what are deal beakers are, what deficits we might be able to overlook in them, and those things that we absolutely can not!

As such, I ‘ve broken these questions down into three categories: Deal breakers, Can I Deal, and What’s Your Deal?  I explain each in detail below.

pexels-photo-1061142Category 1—Deal Breakers (DB) are cause for automatic dismissal as a potential mate, because it means the person will bring to the relationship much drama and emotional baggage from the start.  These questions are:

  1. Are you married? DB if the answer is yes!  Don’t even ask for details!
  2. Are you separated? DB if the answer is yes, again, no need for details!
  3. Have you ever been in a relationship where YOU were completely faithful? DB if the answer is no! Don’t think they’ll be different with you?  They wont!
  4. Have you ever gotten physical with someone you were in a relationship with? DB if the answer is yes, unless the physicality was self-defense.  Even then, beware!
  5. Do you want to be married? DB if the answer is opposite of what you desire—Don’t fool yourself into believing they’ll change!
  6. Do you have issues controlling your anger? DB If the answer is yes or vague—you don’t need those problems in your life!
  7. What are your feelings regarding sex? This includes questions such as: Do you enjoy sex? How long do you think is appropriate to wait before engaging?  What sorts of sexual acts are off limits?  Is there anything about your sexual history that I should know?  Seems like a lot to ask within the first three dates and very personal too!  I say, why wait?  No need getting attached to someone who’s frigid, who believes in no sex before marriage, when you don’t, or who enjoys sexual activities you’d never engage in.  Sexual compatibility can be either glue or, a wedge!
  8. Are you interested in a committed relationship? With Me? By the third date, you should know very clearly if the person wants to be in a committed relationship and they should be able to answer whether they can see themselves doing so with you.   Asking this question directly can eliminate weeks and months of wasting time with  with someone looking for a casual fling when you want something serious!

 

pexels-photo-1061141Category 2—Can I deal?  Although these questions should be asked to get a better gauge of a potential mate’s values and/or how they view and deal with important relational issues, they may not be cause to instantly dismiss the person as a good mate.  Their answers will, however, help you decide the appropriateness of moving forward with them, only after fully accepting exactly what they’ve said, (not the potential of what you think they might be later!)

  1. Have you ever been married, if yes, how many times? An answer of no to this, from someone who is older (say, 40+) could potentially indicate one who is afraid of commitment.  Contra wise, someone who has been married multiple times may indicate someone who has major issues staying committed as well. Tread lightly!
  2. What is your take on Divorce? If divorce is against your faith, or you grew up watching your parents weather through a 30 year marriage, you might not be compatible with someone who feels that divorce is okay in certain situations, or, who suggests they would ask for a pre-nuptial agreement from a spouse.  It speaks to their take on the concept of “for better or worse” and having such a conflict in ideologies may prove problematic later.
  3. Have you ever been with, or do you sometimes desire being with the same sex? Sexual fluidity is a real thing for many people and it’s best to be clear on this very early. Whether you can accept someone who is bi-sexual, or who’s had same sex experiences, etc., is up to you; you owe it to yourself to know this before deciding to go forward with any mate!
  4. Do you have children? Do you want to be a stepparent or would you prefer to be a dynamic duo with someone with whom you can start a family brand new? Children are an extension of any relationship, so this must seriously be considered.
  5. If yes, do you see them? If the answer is yes, skip to question 13.  If the answer is no, this is a significant problem.  A man or woman who has no contact with their children and/or doesn’t support them, financially or emotionally, is likely suffering from issues that are hidden beneath the surface.  To refrain from also becoming entangled, I’d suggest putting this individual in the Deal Breaker category!
  6. If you see them, how often? If a person has children and you’re okay with this, it’s vital to know how often they see their kids.  A responsible, loving parent will have consistent contact and interaction with their children and do whatever it takes to maintain that.  Anything less suggests you should raise your brow!
  7. What is your relationship like with your child’s/children’s’ mother or father?  If the relationship is amicable, that a positive sign, but if there are feelings of disdain or hate, this suggests something deeper that you may want to move on from!  You should also know whether the relationship is excessively enmeshed, or, if there are multiple baby mothers/fathers, as these things can be problematic as well.
  8. Why aren’t you two still together? Having children with someone is a world-changing endeavor, as such, knowing why a person chose not to be with someone with whom they brought a life into the world with, is a fundamental part of understanding what they value and how they view responsibility and commitment.
  9. What’s your relationship with your own mother? Father? Family? Relational strains in any of these departments may be indicative of character flaws and emotional baggage that will show up later.  Know this early and proceed with caution!

 

pexels-photo-1061140Category 3—What’s Your Deal?  These questions simply allow you to gauge how a potential mate thinks, and if the two of you have similar visions for your life. 

  1. Do you have a five-year plan or long-term goals? What sense would it make for you to have specific plans/goals for your life and not be fully aware of the same thing in a love interest?  Discovering the answer to this question will let you see if their plans align with yours, or whether the two of you are on completely separate paths!
  2. How would you go about handling a conflict disagreement between us?  This question gives insight into how a person communicates?  Do they resort to the silent treatment or name-calling?  Do they shut down after an argument or when they’re mad?   Poor communication and conflict resolution skills are a sign of immaturity and definitely something you should absolutely know!
  3. Would you have a problem putting me first if we’re in a committed relationship/if we were married? This question illuminates how involved a potential mate is with their family and/or friends, and whether they would be able to prioritize you above them.  Not all people see this as necessary, as such, it’s a good question to ask!

This list is not all encompassing– are there questions that you think should be added, or ones that you think are not necessary to ask.  In addition, let us know if you’ve ever gotten into a relationship with someone you found out later you really didn’t know?  We want to hear from you? 

 

            

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79 thoughts on “Dating and Relationships: 20 Questions to know by the 3rd Date!

  1. Some of these questions do seem a little intense for a third date, but then it’s been so long since I dated (been married 8 years) I can’t really remember what was normal for me!

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    1. Indeed, a few of the questions are intense and very forward, but hey, whose got time to waste with the wrong person–. Waiting much longer and there’s the chance of making decisions with your heart instead of your mind.

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  2. I completely agree with this list! If by the third date a person don’t know at least a third of these things then at that point time is being wasted.

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  3. This is such a thoughtful and helpful post. It’s so easy to get wrapped up in the joy of an early,relationship without thinking clearly about the long term. I particularly appreciate how you included questions about their relationship with exes and family. That’s so important!

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    1. I think that’s how we’re taught to approach dating– by taking it slowly. I’m suggesting to only take your time (slow down if you will), after you’ve gone through a full vetting process. Unfortunately, people miss the vetting process altogether.

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  4. What a comprehensive guide of dating and relationship questions to know by the 3rd date. And most important is one should never ignore the red flags as things get complicated later!

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    1. Congrats on going 7 years strong!!! These questions are just a guide, but I’m sure there are some on this list that even married couples would do well in asking each other. There are always things to learn about our mate. Communication, whether dating or married, is key!

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  5. This is soooooooo good! It is so nice to see someone teaching about how to be intentional and wise in the process of figuring out who to walk through this life with!! Thanks!!

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    1. It could be awkward indeed, but, if you have a little finesse about you, the questions could be asked in a non-threatening way. Just depends on how serious the potential mate is– someone who also doesn’t want to waste time would likely not be opposed to diving deep so soon. Someone who just wants to play will probably just want to avoid.

      Liked by 1 person

  6. I’ve been married for 8 years now, but before I met my husband, these questions could have saved so much time and heartbreak. I know it will be so beneficial to many people out there just starting out dating somebody and not knowing these important factors. Thanks for sharing, and I am sorry you had to experience being with someone leading a double life.

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    1. Whew– that’s a whole other topic to dive into– teen dating! But, you’re right, it absolutely feels horrible to be betrayed, which is exactly why women and men who are dating need to ask the tough questions.

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  7. Ugh! I am so glad I am over this phase. Nowadays, it’s like a chore trying to know someone in hopes they are truly who they claim to be. I will pass this interesting tips to my single-nistas. (^_-)

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    1. Yes, it’s like all of us married folks feel off the hook with this one, lol. We aren’t though. There are still so many things to learn about our spouses. We have the tendency to get too comfortable and miss the fact that with life, we change. Keep asking questions my friend. Much luck to you.

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  8. I think these questions are very reasonable to know about a person you are having a love relationship with! I stopped dating when I was 18, at that age, many of these questions hardly apply as we are so new to life and adulthood, right? Yes I married my teenager love and since then we’ve grew up together, that’s another possibility I suppose!

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    1. Wow– it’s cool to hear from someone who married so young. That’s a topic all unto itself. I would guess that being so young when you got with your spouse, that the two of you were developing, mentally and physically in a myriad of ways. We can make the mistake of assuming that because we grow with some one physically, that we are automatically growing with them emotionally/mentally, but that is not always the case. Communication and heart talk is essential to continuously know your spouse on the deepest level. May you and your hubby have many more happy years.

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  9. In hind site these are important questions we know we must ask when we are dating a person but tend not to. Thank you for sharing your stories and emphasizing how important these questions are.

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  10. These are great questions to know about a person when starting to date them. Often times people jump into relationships without knowing much of anything about their partners which is terrible.

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  11. What an awesome post. These are really great questions. If only I could turn back time I would actually ask the same thing to my ex-husband too. lol

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    1. Hey, sorry to hear that your marriage didn’t work out, but, I’m believing for you that the best is yet to come. We live and learn in this life, often only after acquiring many bruises. Wishing the best for you going forward.

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  12. Unfortunately you do meet people who live double lives out there. I still believe in honest people though, that you get to know bit by bit as you go on dates with them.

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  13. This is a great, well thought out article! My husband and I got married quickly, but we had an odd first date, he was awkward and I was so shy I couldn’t answer a single question. Instead of giving up we decided to a second date and did one of those silly surveys, where we went down the list and asked random questions. We got to know each other SO quickly and so thoroughly and I swear, asking the right questions early on helped with our relationship!

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    1. Wow– how cool! My husband and I also married quickly and many of these questions were answered as well in a very short amount of time. I think that is why were able to do it so fast though, we didn’t waste a lot of time with unanswered questions, which let us get right to the good part– building a life with each other. Thanks for sharing your story.

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  14. I agree it would definitely be nice and useful to know all of this by the 3rd date. You could definitely save yourself some heartache and wasted time 🙂

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  15. On our third date, second time around, my husband and I figured things out with more serious conversations along these lines. Great questions to make sure that you find someone looking for the same type of healthy relationship!

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  16. These are all great questions. You want to be on the same page as a potential partner! My boyfriend and I had a similar conversation early on and I’m so glad.

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  17. Great ideas and make me realize how much I don’t miss dating! Glad I found my prince charming after kissing so many frogs 🙂

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