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Questions Every Online Dater Should Ask

Questions Every Online Dater Should Ask

Questions Every Online Dater Should Ask

Get The Questions Every Online Dater Should Ask & Stop Wasting Time Dating Mr. or Ms. Wrong

Advice Seeker :
Dear April Masini,

I have always been a shy person when it comes to talking to girls. I don't have a lot of experience. I have met someone online in a dating site who seems to be a good person. She sent me a bunch of questions, which I think she may have got them from a women's magazine. She answered the question first and then I responded with my answers to her questions - kind of to see if we are compatible. I would like to ask her a bunch of "get to know you questions" but don't know what to ask. Do you have advice on the questions I should be asking my potential online dates?

Ask Away


April Masini's Advice :

Dear Ask Away,

What a good question you asked! And how clever of you to know yourself well enough to recognize your shyness.  Using online dating services as a tool to meet women  is perfect for someone like you.

I always advise my readers that knowing yourself is more than half the work you have to do to be in a happy, successful relationship. Knowing what you like and what you think you’d like in a partner will allow you to ask questions to rule out any incompatible matches – and the same goes for your partner to you. It’s not really a rejection when someone knows that you’re not the one for them – it’s saving you time from being with Ms. Wrong. So you have to view your questions to her the same way. The more careful and thoughtful your questions, the better you can rule out someone who’s time you’re wasting! Not to mention your own.

So, let’s go:

1. Is she single?

I know this sounds crazy, but you want to make sure that the person you’re talking to truly is single. Some people have separated from their spouses, physically, but not legally. Unless someone has a legal separation document, they are still married. Some people say they’re separated because they want to be separated, but they’re still living in the same house with a boyfriend or husband. Even if they’re not sharing a bedroom, you still don’t want to get in the middle of this one! So make sure she’s single.

2. Age.

You can ask a range if you don’t want to make a woman feel uncomfortable about giving you numbers. Over 18 or 21 is a good range to start with. A woman over 35 is going to have babies on her mind a lot more than a woman between 20 and 30. So make sure you know what age range you’re looking for in a woman, and that you confirm that she’s where you want her to be. And if you don't want to be so straightforward and ask her age  ask if she's voted in the last election or if she's been in a bar lately -- at least you'll know she's old enough to vote and drink!

3. Physique.

Face it. Chemistry is important. How a person looks to you is important. I recommend dating someone who’s posted a RECENT SERIES of photos – not just one picture. You can absolutely ask for pictures. If someone doesn’t want to post a photo, that’s fair – many women feel unsafe posting photos on the web – however, be prepared for a range of what “thin” or “slim” may actually be. Be honest about your own physique. Again – you’d rather see your online date sigh with relief, or grin with delight when they set eyes on you for the first time rather than back up two steps and check for the door. Don’t be rude by asking for specific measurements. But you can ask, are you more Jennifer Aniston or Pink? Are you Gwen Stefani or Paris Hilton? Asking if they work out at a gym or exercise will give you a good hint to their body type. You can also find out the fat factor by asking, are you more Ricki Lake or Paris Hilton?

4. Religion.

You shouldn't ask someone's religion if you're hiring them for a job, because you may be discriminating. But if you're Catholic and you really want to marry a Catholic woman, it's okay to tell her your preferences. If this category is a deal breaker for you, be honest about it -- with yourself, and your date. The whole reason you’re online dating is to pick and choose. So if you want someone who is religious or not at all religious or practices a certain religion, mention it. If you want someone who doesn't believe in religion or spirituality, it's okay to ask for that as well. As long as you're respectful of differences, asking is fine.

5. Education and career.

There’s nothing wrong with a high school drop-out – for some people. Others only want to date people with doctorate degrees. Some white collar workers love blue collar workers. Others don't. Are you okay dating a freelance artist or would you rather date someone with a steady job? Know this about yourself, and then ask. Some people use the internet dating services because they’re so busy with their careers that they don’t have time to meet people at coffee shops and the park. Yet, others use internet dating services because they have a whole lot of time on their hands. Find out where your date is in that spectrum.

6. Children.

Does your date have children? Get this one out of the way up front. There is nothing wrong with telling a potential online dater that you don’t want to date someone with children, if in fact you don’t. Believe me, a single mother wants to be with someone who wants her and her kids – so it’s best for you to be honest.

7. Hook up or heart connection.

What kind of relationship are they looking for? If someone’s looking for a one night hook-up and you want marriage, it's better to establish that up front. Ask them their relationship history. Longest relationship, shortest relationship, what broke them up, and how many relationships in the last 2 years have they had, etc. This isn't just a good question to ask to get information -- it's a good question to start a conversation about relationships, hopes, and dreams. You'll find out a lot about your potential date with this one.

8. Safety and health.

Anyone close to you in jail? As awkward as it may feel to ask – it’s better to ask the hard questions before you meet. Any drug abuse in your past? Some people who are AA only want to date other people who are AA. So ask. And anyone who balks at your questions will be telling you that they don't believe that your interest in this subject is important. On the other hand, you may earn someone's respect for bringing this up. They may want to know the same about you, and didn't have the words to articulate their question. They'll be glad you did.

9. Fun factor.

What’s your fun like? If you’re a shopper and a lunch-er, you may not want to get involved with a heli-skiier or a race-car driver. But then again – maybe you do! You'll also get a good idea about what kind of dates you'll both enjoy when you ask this question and hear the answer.

10. The perfect date.

What’s your idea of a perfect date? Dinner and dancing? Or bowling and a taco stand? Find out about your date’s romance IQ and give a hint of yours at the same time. Need some ideas, check out my new book Ideas For A Fun Date.

Bonus questions: What was the biggest mistake you ever made? What’s the best thing you ever did? Who’s the most important person in your life? What’s the most important item you ever bought? What would you buy tomorrow if you could buy anything? I bet that these questions will stimulate your own question asking -- and your questions to your online date will stimulate hers, as well.