10 Insightful Questions to Ask a Dating Prospect

Let’s be real and get down to business, time is money and money is time. In a day and age where technology brings business, communication, information, and connections to people in an instant, we move fast and don’t have time to sort through a complicated mess. Nevertheless, we want to date, that hasn’t changed, but how we do we cut to the chase to find out what someone’s about. This article discusses 10 questions to ask a person you’re interested in potentially dating. And before you ask these questions of a dating prospect, you should answer for yourself first, to know where you stand and relate when you ask.

1. You only see your family once a year, what would you choose for the holidays–going home or a trip to the Caribbean? And why?

What this reveals: Well, obviously, this tells you a lot about what their priorities are. Granted, everyone wants to go on vacation, but had they been very into family, they would’ve found another time to go on vacation besides the holidays. More times than not, the end of the year holidays are about family, it’s the rare time when everyone is able to get together. Maybe they really like vacation over the family holiday traditions, which is fine too, IF that’s what you’re looking for. The thing that can be worrisome if you’re looking for a marriage partner, is the fact that there could possibly be some kind of rift in the family. Every family has issues, needless to say, but long drawn out harbored conflicts are not a good sign. There is also the possibility someone would just choose a Caribbean vacation for just a particular year just to get away from family, be alone, and get some good R & R (cause we know family gatherings can be less than inspiring for R & R). You should really listen to their why and understand what their motivation is, it tells you how they feel about the first F–family. When I talk about F’s, I’m referring to the 3 areas that one should look out for when dating (and no, none of the F’s are bad 4 letter words). These are: 1) faith, 2) family, and 3) finances. See if their motivation for family is the same as yours.

2. If you have $1000 dollars, how would you spend it?

What this reveals: Like I said, this is another F word, a good F word that is! Finances! Finances are one of the top problems that marriages can have. And as much as we want to be on cloud 9 when we’re dating or in love, the tire hits the pavement when it comes to finance talk. One less obvious thing to note is how calculated they are when it comes to their breakdown, it will give you a hint to their spending style. If they tend to be very approximate of their spending categories, chances are that they are well versed in budgeting. Some people will be so meticulous to be precise down to the cent. Someone who quickly throws out some numbers is a little carefree with their money. And of course, the person who keeps the $1000 without spending will tend to be your saver, possibly very much the penny pincher. How you line up with them in this issue will set the stage for your future financial issues. Of course, one can learn from the other, but it’s good to understand what value the other party places on money. All financial issues have emotional issues behind them. Maybe they save a lot because they’ve been laid off before and know what it’s like to live with no income. Maybe their parents took them shopping every weekend or bought them gifts constantly without regard for cost. Understanding their finances early on helps you understand their background, how they grew up, and your potential future. And, if at all possible, it would be good to exchange credit reports, It’s the best succinct piece of paper to tell you the financial story of a person.

3. Your child gets pregnant at the age of 17, what do you do?

What this reveals: Yeah, this is a pretty deep question, but in the dating game, we’re supposed to get to know each other. And these insightful questions do just that. A person’s faith will play importantly into this one, as it will give insight to their right-to-life/pro-choice views. Although faith may not be an active part in your life right now as a single person, that may possibly change when you have a family, which I have seen in so many of my friend’s families time and time again. A few more issues that come into play are: 1) trust, 2) forgiveness, 3) resolving problems, 4) regard for reputation and 5) level of being judgmental. These are important value stances and shows their ability to resolve life’s hardships in their lives. Regard for reputation is an aspect most people don’t think about, but it’s important to know how much this does or doesn’t matter to your mate. I once dated a guy who lived for his reputation, whereas I, on the other hand, lived my life according to my rules and what I thought was best, regardless of what people thought. Needless to say, this caused a lot of problems as he would constantly point out my ‘inappropriate’ behavior’, while I was carefree in that area. Life will often hand us some kind of crisis, it’s inevitable and how each person handles it tells you 1) what it’s going to be like in tough times with them and 2) whether they’ll fight or take flight. In the beginning of dating or any relationship, life is grand, the grass is greener than ever and there’s no clouds in the skies. It’s easy to think you’re compatible, but when you have a big crisis come up, you’ll see how compatible you are with their moral stance. It’s up to you to decide where you can compromise and where you just aren’t in agreement.

4. Should you be friends with your ex? Why or why not?

What this reveals: One can choose to look at this negatively or positively. Some people live in absolutes, where their mind is set on a certain way of doing and looking at things. That’s the way a lot of people live, it’s a much more safe place to be within certain boundaries. For some people, that works. And then there are those very few who choose to do away with boundaries and go down the off beaten path. Nothing in life is certain and these people know that, many answers to situations for these folks are ‘it depends’. And so, in this question, for these folks, it depends. I have walked away from most relationships and dating situations in a good light. I’ve always valued people in my life and tend to keep people in my life regardless of what may have happened. These exes are valuable friends to me as they know me better than most people. They’ll listen, care about me, and be there should I need them. The best example of this was the day that my father passed, the majority of my exes called that day offering their condolences to me and also in memory of my father whom they very much respected and cared for. Of course, in any future situation, this will require a man to have great trust in me with these relationships that are now a part of my life. However, should the ex in your case be one that’s meddling, deceitful, still in love with you, or have bad intentions, it’s not a good idea to keep them around. And if all your prospect’s exes tend to end badly, you may want to look at your prospect as the source as well. Not every relationship has to end badly if properly handled by the people dating.

5. What’s more important forgiveness or faithfulness? Why?

What this reveals: This is obviously a non win situation. There’s no easy answer to this question, both are very valid aspects to have in any relationship. But, this is nevertheless, a question that reveals much of your prospect’s character. Should they choose forgiveness, then obviously they will come with a personality more apt to accept that bad things happen and forgiveness is always needed. No one is perfect, and your new prospect is not, by any means. Learning this is important, as one of my married girlfriends told me, ‘I wake up and forgive, and then everyday, I do it all over again’. There is no shortage of reasons to forgive–big or small. Well, what about faithfulness? Of course that is an admirable characteristic. It’s one that makes a person feel secure and that they’re able to trust their partner. Of course, everybody wants that as the end goal of dating. For most it would be ideal to have that, whether in a marriage or a relationship. This is a tough question and paying attention to how they arrive at their answer will tell you volumes on these 2 very important issues. I know there are people out there who will say absolutely no and cut it off should cheating occur. Then I know others, such as myself, who have seen relationships (very few, mind you) become stronger from infidelity. Again, it always depends, but watch to see if this person follows in line with your ideals.

6. If you were stuck on an island what 5 items would you bring?

What this reveals: This is always a fun one to ask. It’s always interesting what people will bring with them. This one is a little less serious than the other questions, but it just gives you a chance to know what’s important to your prospect. It’s good to now always take things seriously, so this is one of those questions that are ‘just for fun’. Of course, part of you would like to hear the other person that ‘you’ would be one of the 5, but it really depends on how long you’ve been dating for this to be comforting or possibly psycho. Should it be a fairly new relationship, the idea of being brought an island with this new person may strike fear in you. I know it would for me. Flattery isn’t always a great thing, it can be scary at times. At least one of these items will reveal to you what is most important in their lives. For me, 3 things I would bring are 1) a journal, 2) a pen, and 3) music. Yes, obviously writing and music are musts in my life. Knowing this, my potential partner could know either what to get me as a present or even more importantly, know what soothes me in my life. Then he’d know if I’m upset with him, to send me away with paper and pen, and I may possibly come back more at peace and at ease. Likewise, some guys may bring their gaming systems, computers, weight benches, you name it, these five things can be all over the place! Listen up to what they have to say and take the chance to understand another side of your partner’s personality.

7. You have a month to live, what would you do for the last month?

What this reveals: There are so many ways to answer this question, besides any kind of violent sort of answer, pretty much anything said goes. One of the most obvious things this reveals is how much they treasure life, whether it’s to travel to places they’ve never been or to be with family. Knowing where they go with this shows where their heart is and is a very important aspect to know. And, then there will be those who view it negatively and would just spend the last month soaking it in, feeling bad, or hiding from the world. Naturally, these people would either drain a partner’s energy or could possibly be uplifted by having a positive partner. You’ll have to be the judge of the dynamics between the two of you. For me, the closest I have been to this was to be around my dad his last month of living when I lived out of state and was jobless at the time. That month was one of the most intense months I’ve ever had when I decided to move to be near him. And I constantly tell people over and over that if I had to do it all over again, I would’ve done the same while being jobless. I would’ve taken being jobless any day to be able to have that time with my father. Jobs will come over and over again, but that time with my father only came once.

8. You can only have 2 electronic items with you for a week, what do you take (cell phone in this case would have to be a regular cell phone with text only, no smart capabilities)?

What this reveals: This is a funny, interesting one. Just like the ‘5 things on an island’ question, this one is similar, yet different because this one reveals how attached one is to their electronics. It goes without saying that if they bring their cell phone, they like talking and/or texting. They’re much the communicator and need people around. Perhaps you’re not a very social person, knowing this, you’ll know what you’re up against when it comes to social aspects of the relationship. I’ve met couples before where one person loves to go out and be social, while the other stays at home. Eventually, they fall to their differences and break up or divorce. And, many guys will most likely bring a gaming system with them, which signifies a gamer in your hands. Every guy has a kid in them, and this is one of those aspects where women would be wise to accept and not try to change (with the I’m gonna change the man attitude that so many of us women have). In everything there’s a time and place, such is the case with their gaming system. Just as some of us women need our girls nights out or our shopping time, guys need their escape. I always found a way to intertwine my time with his while he played, by being right beside him doing whatever it is that I do while he plays. It worked for us, which goes without saying, any couple can work through differences and come to meet in the middle. Of course, what would be ideal would be that your prospect asks you what’s important to you and brings those items, so you can share. In a perfect world, that would happen, but there’s many of us who are selfish and only see this in light of what we need. So, it would be very natural to have them answer as a singular person.

9. Would you rather be deaf or blind, and why?

What this reveals: This tells you very much whether the person you are with is a visual or audio person. Obviously if you’re with someone who chooses to be deaf, most likely they’re a people watcher and this is helpful for you to know to be on your best behavior because you know they’re watching you quite frequently. Likewise, should they choose to be blind, they’re definitely audio people and will pay attention closely to what you say exactly. Knowing your choice would give you an idea of where the two of you would stand. I’d be in a lot of trouble with a blind person, as my words would be deeply evaluated and considered. I tend to say whatever with care to the wind, for some my words would be depict an exact picture of who I am. Should they choose to be blind, if you wanted, you know you could get away with not being in your best dressed clothing all the time. Other considerations would be how much they want to be noticeably disabled. A deaf person most likely would go more unnoticed than a blind person. This goes back to where the person values their reputation and image.

10. Your best friend tells you, they cheated with your current girlfriend/boyfriend, if you had to choose only one, do you keep the best friend or the girlfriend/boyfriend?

What this reveals: Yes, this is another loaded question. No one wants to be put in a position to choose, but then again, nobody wants to be in a position of being cheated on where their best friend is involved. It comes down to friendship or relationship. But, at certain times, it may not even be a choice of either/or, some may choose the route to choose to not have either person in their lives. After all, they’re supposed to be 2 of the most trusted people in your life, and they both happen to betray you. After all, if they’ve done it once, the partner or the cheater may come back around, depending on which you keep. It’s not a very pretty scenario. Having the best friend come forth first shows an important aspect that they can be more honest than your partner. They become the lesser of two evils. Sometimes people will tend to stick with the best friend as another boyfriend/girlfriend will come around, is what they reason. Best friends really are hard to come by and their friendship has obviously outlasted the time and struggles that they have come across. Both are difficult options, but yet again, this gives an insight for you to whether forgiveness with friendship or a relationship is more important.

Getting to know someone new is never an easy thing. Besides the normal subjects of interests and hobbies, understanding someone’s moral stance and values will reveal much of their character and you can decide how it fits or doesn’t fit into your life. There are no right answers, they’re just about what’s important to you and to get to know the other person. These aren’t your everyday ho hum questions, but they’ll give you power insight into who they are as a person. Dating isn’t an easy, but asking the right questions can help you navigate through all the things going on.