8 Online Dating Questions to Ask Men

By on August 19, 2015

The dating game is hard, and online dating is a whole different ball game. You don’t get to see potential match ups face to face, leaving all of your communication and flirting to be done via internet. So what kind of questions are best for a new, potential boyfriend or girlfriend? We’ve come up with 8 awesome questions that will help you get to know this new certain someone and see what they’re all about, before you take it to the next level.

1. What part of my profile made you want to contact me?
You should always know WHY someone ‘approached’ you and picked YOUR profile out of the rest. Was it your stunning profile picture, or the witty ‘about me’ section you spent 3 hours putting together? The answer to this question could tell a lot about your potential match. I mean, it’s great they were attracted to you and clicked on your picture out of curiosity, but did they even take a second to read over your profile before sending over a message? This is a great starter question that will open up the door for plenty of other fun communications.

2. What are you looking for in a woman?
Finding out right off the bat if you’re even his type is an obvious must. I mean, if he likes a quiet, shy girl with a degree who loves to read and write and you’re more of an outgoing gal with a different event planned every day of the week, you might not hit it off. Find out what he’s looking for, and if it sounds like you may be the girl of his dreams, keep talking. (And obviously find out if he has all the qualities and traits you’re looking for too!)

3. What are you looking for in a relationship?
Whether you’re meeting someone online, at a bar, through a mutual friend, or at the grocery store, you should always inquire about what they are looking for. Men and women tend to be a bit more blunt and honest on online dating sites since they aren’t face to face with the person on the receiving end of the message, so you’ll probably run into a lot of people blatantly stating they want a one night stand. And if that’s what you’re looking for too, by all means, go for it. Either way, find out whether he’s looking for a fling, to casually date, or wanting something long-term.

4. How long did your last relationship last?
Is he new to the game and never had a girlfriend for more than 3 days, or has he just gotten out of a marriage? Knowing his or her relationship past can help you to determine how understanding he is of relationships and whether or not he is going to be a long-term thing or not.

5. Why did your last relationship fail?
Trust me, you want to know the answer to this question. Did their relationship fail because he was a routine cheater? Or did the love of his life leave him for his best friend? Was it a mutual breakup because the chemistry died off? Just like any other conversation, you don’t want to keep prying about their past relationships, so try not to keep pestering if they don’t feel comfortable answering just yet. If you find this individual interesting, keep talking and eventually they may go into further detail about why their last relationship failed.

6. What is your best quality?
Everyone has that one special quality they love to flaunt, whether it’s their undying love of helping people or their ability to hold their breath underwater. You may be really surprised by the answer this potential match gives you, and it’s an easy way to learn more about their personality and the type of person they are. Just be prepared to answer this question in return!

7. Why did you choose online dating?
This is really just a fun question that everyone has to ask when it comes to the online dating world. I mean, after all, with so many places in the world to meet people, why would you turn to online dating? Did they do it for the convenience of relaxing in bed in their pajamas while chatting with their potential soulmate, or are they so incredibly busy with work they simply don’t have time to step out and meet people? So many interesting answers await!

8. What are your future goals?
When talking to someone you are interesting in, you NEED to find out their future goals right away. If he doesn’t have a single goal on his horizon other than managing to eat 3 hot dogs at the same time, you may want to move on. The two of you should have similar goals that you will be able to work on together and act as a support system for one another. If you want a big house and 3 kids and he dreams of traveling the world in his Ferrari with 0 children, that’s a definite mismatch you’ll want to know right away.


What online dating questions do YOU always ask?


  1. Dating

    August 23, 2015 at 7:03 pm

    Have you ever tried not to give your picture immediately? You can for example instead say, “I assure you, I look completely normal woman of my age, but I prefer to give you my picture only after I know you better”. If the guy is still interested then you’ll know he’s interested in what you have to say, not just how you look.

    • web admin

      web admin

      August 23, 2015 at 8:30 pm

      That actually sounds like fairly decent advice in a way. I would assume that someone who is just looking for a fling would want the photos immediately and would want the photos to get sexual fairly fast. At the same time, there are a lot of problems with people using old, outdated photos on their dating profile–the guy may get worried if they do not get a recent picture. All the same, I like your advice. Thank you for commenting!

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