10 Best Question to Ask on Dating Websites

Dating Websites

When faced with getting to know strangers on dating websites, you are left with a minimal number of ways to accomplish this task. You could ask for their social security number, birth certificate, and a blood sample. You could ask for a list of references. You could ask for an address from which to stalk them from afar, or simply come up with a couple of questions to find what you need to know within the first couple messages. Here are the ten best questions to use on allwebsites.

1. What was it about my profile that first caught your attention?

One of the biggest dangers of all dating websites, are the jokers who use “form introductions” to send out mass invitations to hundreds of eligible singles. Their only standard is that the person is either hot or cute, and if they’re neither of those, they prefer them to at least be willing to wear a bag over their head if the occasion calls for it.

2. What are you looking for in a relationship?

Members of dating websites are often surprisingly honest about this question. They may be looking for fun, sex, friendship, or a shotgun wedding, but you’ll never know unless you ask.

3. What are the three most important tools to achieving a great relationship?

This question can tell you a lot about someone. One, it will hint towards their relationship style (giving, taking, loving, etc.). Two, it will tell you what they consider to be a great relationship, and three, it will hint at their priorities (ex. responding with three different sex tools, rather than emotional ones).

4. What do most men/women fail to understand about each other?

While this question is asking in general terms, which is less threatening, you can expect it to refer to troubles they’ve had in the past (cheating, lying, etc.). All sorts of bad relationship tendencies can be hidden within someone’s opinion about men or women as a whole, so make sure you read these with care.

5. What are you most proud of?

This open-ended question will allow a member to sell themselves to you, but what you’re really looking for is what it reveals about their passion and drive in life. In other words, what they value the most, whether it is money (material objects), honesty, freedom, religion, vanity, relationships, or family.

6. If you could live anywhere, where would it be?

They say love is all you need, but it is important to agree on where you’d like to hang your hat when it’s all said and done (or at least be willing to compromise). Some people are a little country. Others are a lot more rock and roll (city).

7. What was the worst lie you ever told someone?

Lying to other members runs rampant on most dating websites. While you can’t expect people to be completely honest with this question, it can catch a lot of people off guard, prompting them to confess to a prior relationship or financial infidelity.

8. If you won the lottery, how would you spend your reward?

Couples fight a lot about money, and this is often because they do not have a common understanding about where the majority of their funds should be concentrated (savings, investing, or buying worthless stuff). This question may not be a foolproof method to avoid a dangerous spendthrift, but it can send up a few red flags to keep your eye on.

9. Where do you see yourself in 10 years?

Some members have no plans further than getting drunk the next weekend, and this question will sort them out without having to experience their mischief for yourself. Sometimes it’s okay to live life one step at a time, but if you have definite goals as to where you’re heading, it’s nice to be with someone who at least has the same set of direction in mind.

10. What are the top 10 items on your bucket list?

Bucket lists are a popular topic these days, as they allow us to think about what is truly important to accomplish before we die. This question will not only tell you about their goals and aspirations, it will hint at their priorities, values, and most importantly, their level of creativity. Believe it or not, a person’s creative nature can make or break the future of any relationship.

About Eric J Leech

Eric is a dating expert and professional blogger.


  1. Really theare are many dating websites.really it is a great post.and i love your dating website.


  2. Thanks for your comment James! Glad to see you like the post

  3. I like the fact that you asked open ended questions which actually lead to a conversation. So many times people get into the habit of interviewing the other person and it reads like a job interview. Good advice!

  4. Thanks Nick! I’m glad you agree that open ended questions are the best way (in most cases) to get conversation flowing


  6. Prosper, I would love to send you some tips on dating! just shoot me an email sometime and I’ll see what I can do for you. eric@datingwebsites.org

  7. there are so many dating websites in the world it is very important to find the one who provide the best service. nice post thank you for sharing.

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    “10 Best Question to Ask on Dating Websites | Soshable | Social Media Blog”.
    Anyway I really admired the post!Regards,Denisha

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  23. Michelene says:

    Hi Eric-
    This was such a great list of questions. Very helpful in figuring out other people. I have a question about a website that I came accross a few months ago. The website asked my racial and ethnic background. Then it asked me if I prefer to date only those within my racial or ethnic background or if I don’t have a preference regarding my dating partners background.
    Is this an ethical question to ask? I can understand why this might be helpful because people do have preferences. For example, I’m white of European decent but I am usually attracted to others outside of my race and ethnicity. Would you consider this question to be a method of racial profiling?

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