In the online world, there is no opportunity to gather information about a person naturally, as you would with someone you go to school with or work beside. Instead, you have to learn about your prospective date purposefully, by asking some pretty direct questions. Because of the anonymous nature of online dating, there is room for intimacy and freedom of expression in both asking and answering questions. But this same anonymity can lead to misunderstanding and hurt feelings, not to mention plain old bad manners. What are the right questions to ask, and how can you pose them in a way that takes advantage of the freedom and opportunity of online dating, yet does not appear rude?

The three sets of questions that follow are designed to walk you through the initial phases of online dating with integrity and openheartedness—and to encourage the same in your potential partner.

The first is a list of question to ask your potential date to decide whether or not you’d like to meet. They are meant to establish any non-negotiable social, financial, or spiritual/religious issues that, if you knew them in advance, would prevent you from going out with this person in the first place. Although most online dating services ask about these areas already, it’s still good to address them a bit more deeply when you know the issue is particularly meaningful for you.

The second focuses on questions to ask on a first date. These are much more playful and fun! Now that you’ve gotten the hard stuff out of the way, you can focus on getting to know each other and discussing individual priorities, joys, and sorrows.

The third continues in the “getting to know you” vein, but focuses specifically on spirituality, whether or not it is attached to a particular religion. No matter how specific or vague, doctrinal or individualistic, most people have a personal view of things like compassion, the nature of the divine, and even the purpose of life. These questions are designed to provoke conversation on these fascinating topics and allow you to get to know the inner man or woman, beyond appearances.

At the end of each set of questions, you should know whether or not you’d like to continue exploring a relationship with this person. I’ll provide simple suggestions for how to communicate that you want to take it to the next level—or not.

Remember--outside of your gateway issues, disagreeing on answers to hard questions is not a sign that the relationship can’t work. You could disagree on everything and still find each other irresistible. Or you could have perfectly matched answers, yet find dating to be a giant snooze-fest. So don’t misinterpret mismatched answers as a sign of incompatibility. Stay open just a little bit beyond your comfort zone. You never know what can happen when you’re open to a genuine dialogue.

What to Ask in Those First Emails

Spirituality. Money. Children. Health. There are the four areas where, should your answers not match, there may be no point in going on a first date. But these are often the last things we discuss when we are first interested in someone! When you’re filled with admiration and lust, such issues may even seem irrelevant or likely to work out on their own. But this is rarely the case. Loving someone doesn’t automatically lead to loving your life together—and serious relationships seem to fail, not for lack of love, but because the couple wasn't aligned on these key issues.

That said, nobody wants to go out on a date with a person who insists on a full-scale background check. And it’s not appropriate to pry into a stranger’s bank account or medical records. But if you’re after more than some fun dates, if you know you’re looking for a relationship, you can cut down on the heartache quotient by some sense of your essential priorities, and asking your new match about his or hers.

Start by asking yourself if you have any deal-breakers. Must your future soul mate be Christian or Jewish? Are you certain that you can only live in a vegan household or are committed to retirement at age 40?

Here are some suggested questions to pose before you go on the first date. Feel free to change the wording and, remember, if this isn’t an important issue to you, don’t feel compelled to bring it up.


This can be a sneaky category, because its importance sneaks up on you. My husband and I are from different religious backgrounds, which didn’t have much effect on our relationship—until we began planning our marriage. Suddenly, it was very important to me that he step on a glass under a chuppah, as is traditional in the Jewish faith. My feelings took me by surprise! So what may be irrelevant while dating can suddenly become more important should the relationship get serious.

My friend Katherine is a serious student of Buddhism, but her ex-husband was not. She learned from this experience that, for her, sharing the path is central to creating a happy household and so now she dates people who are aware of this. This question offers and solicits straight-up information about a trait that, when shared, is quite lovable.

Question: Pursuing the _______ spiritual/religious path is important to me. I’ve derived tremendous satisfaction from it and being able to share this path with a loved one is a dream of mine. Whether or not you feel the same way, I’m interested in learning more about your religious/spiritual values, if any.

This second question is not about religious/spiritual beliefs or doctrines, it’s about spiritual character. It’s one thing to express your devotion to Christianity or a yoga practice, but it’s another to put that devotion into action.

Question: What three qualities do you value most in yourself?


Grownups, please step to the left and non-grownups move to the right. When it comes to money, this is where the two groups separate! I’m not suggesting that you request three recent bank statements before dating someone, but grownups know that money is important—not for its own sake, but for what it communicates about lifestyle and values.

Here is a reasonable way to ask about material values and goals, as well as how far this person has gone with them. Let’s face it, if you’re looking for a long term relationship, lifestyle is an important issue. Unless you’re gold-digging, there’s nothing wrong with exploring this.

Question: I’m at a point in life where being able to provide for myself without too much worry is important. I’m working hard at this and have succeeded in some ways, but not in others. How satisfied are you on this score?

This next question explores a person’s financial personality and values. It’s interesting to know if his or her family taught the values of wealth, charity, secretiveness, independence, or any of the other commonly (or uncommonly) held beliefs about money. It doesn’t mean that he or she is fated to hold the beliefs learned in childhood, but a discussion of how this is all playing out in adulthood can be illuminating.

Question: What lessons did you learn from your family about money? Which were helpful and which were not?


I’ve had several friends who’ve been in brilliant relationships—supportive, fun, and romantic—but ended up breaking up over the issue of children. When a good relationship has to end over divergent views and not from lack of love, the heartache is especially intense.

Even more than religion, it’s the issue of children that is likely to lead to a relationship impasse. If one of you wants children and the other still isn’t sure; if one wants them right away and the other wants to wait; if one can’t imagine raising children outside (or within) the church, synagogue, or temple and the other feels the opposite—these are topics that provoke primal feelings that may trump even love. Even though it can be uncomfortable, it’s far better to bring it up now if you have strong feelings you will not be able to compromise.

Here is a way to pose the question directly but not in an overly aggressive way. You could even add something about how you recognize the awkwardness of bringing this up before you’ve met, but are doing so out of respect for him or her.

Question: Although I enjoy creating new friendships with a variety of people, I know that I’m looking to date someone who wants children. Do you have any strong feelings about children, one way or the other?

This question communicates your vision honestly without judgment or expectation.

Question: Family is very important to me and my vision of the future includes a partner, children, and a vital home life. In the meantime, I’m happy to date but if I were to get serious, it would be with someone who shared this vision. Is there anything you want me to know about your views on this subject?


This may seem like an odd topic to introduce at the pre-meeting stage, but it’s surprising how important things like smoking, diet, and exercise can become as a relationship deepens.

These questions about health can be posed very simply. There’s no need to justify or explain why you bring them up, unless you want to.

If you’ve quit smoking or drinking for any reason and do NOT want these habits to reenter your life, please don’t be shy about asking this first question, especially if you’ve struggled with addiction in the past. You don’t have to divulge too much information here, just gather whatever you need to feel comfortable before going on a first date.

Question: How much do you smoke and/or drink alcohol? For me, the answer is ________. I don’t think there’s a right or wrong answer to these questions, just curious if our views match, so don’t be afraid to be honest!

If diet and exercise are important to your lifestyle, please mention them. By “important,” I mean that these issues are very high on your priority list. For example, if you’re a vegan or an oenophile, it may be quite important to share these interests with a potential mate. If health and diet aren’t super-central, you can ask this question at a later time.

Question: I try to eat well and get to the gym (or yoga studio, hiking trail, swimming pool) __ times a week (or month). What do you do to keep healthy?

At the end of this dialogue, you’ll probably know enough to determine whether or not you want to go on a date with this person. If so, you could tell him or her something like, “It’s been a pleasure getting to know you and, if you feel the same, I’d like to meet.”

If what you’ve learned has led you to believe a date would be a mistake, you could say something like this: “Thanks for sharing some of the details of your life with me. You sound like a great person, but I think we’re looking for two different things and so the more we may like each other, the worse it would actually be! So I wish you well in finding someone who is looking for the same things you are.” Again, keep it simple and straightforward.

What to Ask on Your First Date

I’ve been on a lot of dates with people who could have been sent down from central casting to fill the role of potential soul mate; it was as if they had been custom-designed to comply with my list of desirable qualities. Good looking? Check. Smart and funny? Check. Good job, cares about others, great kisser? Check, check, check.

Wow, can appearances be deceiving. I’m not saying that people who lied about their professions were really 5’3” not 6’3.” The problem was that although on the surface things looked fine, just below it there were some problems. No amount of accomplishment or good looks can predict emotional balance or internal stability, and these are the qualities that can make a great lifelong partner. The questions below are designed to help you peek below the surface and get to know what this person is really made of, right now. Do they like their job? Get along with their parents? Know how to find pleasure in life? Answers to questions such as these can give you more insight into each other than a thousand “What if?” questions or inquiries into a person’s hopes and fantasies. How is their life going right now? Look at the reality of their life, not their wishful thoughts about it.

Question: Who are your closest friends and how long have you known them?

Like all the other questions, this one has no right answer. However, learning that he or she has had the same best friends since grade school or only has friends associated with work can tell you things about his or her priorities.

Question: Do you like your job? How closely does it match what you thought you’d be doing with your life? What has turned out better or worse that you anticipated?

Dating someone who has confidence in their career path (whether or not it matches what they thought they could or should do) can indicate a person who has reached some sort of peace or creative satisfaction within him or herself.

Question: What was your relationship with your parents and /or siblings like when you were a child and what is it like now?

Again, there is no right answer here, but it can be illuminating to find out that there were struggles in childhood that have been resolved, or that there has always (or never) been a sense of closeness.

Question: How do you generally spend your weekends? Describe your ideal Sunday.

Does he spend all day Sunday catching up on work? Does she have dinner with her sister every Sunday? Is the weekend a time for escaping the realities of life or for exploring other interests? What you find out from this question is another indicator of values, priorities, and life-satisfaction.

Question: Describe your current living situation.

Does your date live with his or her parents at 35? Have high school friends for roommates? Live alone in a high tech paradise? The home environment is perhaps more telling than any other detail.

Question: Where would you like to be living in 5 years? 25 years?

This question can also reveal hopes, dreams, satisfactions, and disappointments. “I want to be living where I live now” is very different than “As far away from here as possible…”

Question: What have you learned about yourself from the way past relationships ended?

Breakups are never, ever easy. But if all his or her relationships ended because the other person couldn’t make a commitment, didn’t want children, or fell in love with someone else, this could tell you something. It’s also interesting to find out if he or she learns something from breakups, beyond becoming bitter or sad. This is an important indicator of character.

Question: What qualities have past partners appreciated most about you?

This question gives someone a chance to tell you what’s wonderful about them without sounding like they’re bragging…

Question: Who is your best friend and what makes you close?

Not everyone has a best friend, of course. But if he or she does, it can be instructive to learn what he or she values most about friendship: loyalty, longevity, shared interests, respect…all these are possibilities.

Question: What holidays or events did you celebrate growing up? As an adult?

Once again, there is no right answer here, but I’d look for responses that reveal nostalgia, anger, or happiness. They will tell you about childhood dramas and also indicate whether or not there has been resolution.

At the end of the first date, go home and think about what you’ve learned. Do you want to go out with this person again? If so, communicate something like this: “I appreciate getting to know you. Thank you for your openness! If you’d like to go out on a second date, I’d love to.”

If not, try something like this: “I appreciated getting to know you on our date. I enjoyed spending time together, but I think that at this point in our lives, we value different things. I wish you all the best and hope your next date will be just who you’re looking for!”

What to Ask to Get to Know Someone's Spiritual Side

Questions about spiritual life are really questions about a person’s deepest self. Unless you have super-specific religious beliefs that you know must be shared to the letter, look for answers that are rich and complex, or that simply sound honest. Answers that are too simple and pat or vague and spacey could indicate a lack of thoughtfulness and dedication—or simply be a sign that one is still searching.

Be careful with these questions. Ask them with openness and curiosity. They are deeply personal, and therefore it takes work to understand what your partner’s answers mean to him or her. So listen carefully and don’t jump to conclusions too quickly.

Question: Is it important to you to find or follow a particular spiritual path? If so, have you identified one?

This question can tell you something about the depth of his or her spiritual commitment.

Question: What, if anything, do you do in your everyday life to express or support your spiritual interests?

Is their spiritual practice a reality or is just something they practice on Sundays? This question can help you find out.

Question: When and where (if at all) have you felt a connection to God/the divine/spirit/your best self?

Again, does this person have a personal sense of spiritual richness, or are their feelings based on doctrine?

Question: If you had (or have) children, what would you (or have you) told them about God or spirit?

This may be my favorite question of all. I don't think there's another question that can tell you more directly of a person's real beliefs and values. This is where the rubber meets the road. It's one thing to say you're that spirituality is important; it's another to have thought about how this might be taught to one's children.

Question: How do you and/or your family mark important turning points such as births, weddings, and deaths?

This question can help determine the type of background your date comes from and how or if he or she has decided to migrate childhood beliefs into adulthood. Has this been a conscious or unconscious choice?

None of the questions we've explored have right or wrong answers, and that is certainly true for questions about spirituality.

If at this point, you feel intrigued by the answers you've received to the questions from all three dating moments, chances are good that you and your date are off to the start of a fabulous and meaningful relationship.

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