Online Dating Questions – What to Ask a Potential Date

If Dolly Levi were available to assist people with the trials and tribulations of online dating she would probably provide some sort of list of potential questions to ask when meeting someone online that goes a little something like this (cue the music):

  1. What do you do for a living? This is an important trick question that women have been smart enough to ask for centuries and has now been leaked to the masses. Asking what someone does for a living lets you know these three very important things: their gross income range (as well as future earning potential), their interests and basic personality type (peace corps worker versus corporate lawyer—you get the gist), and whether or not you will see them very much (US Marine versus Innkeeper).
  2. Do you like where you are currently living? While this question seems innocuous enough it is really quite exploratory.  It is a way of finding out whether or not they still live at home with their mother, if they have roomies from hell, if they live in a safe part of town, or if they are still residing with an “ex”. For example, if the person says that their house is in an up-and-coming part of town what they are really saying is that their windows and doors have metal bars on them due to the extremely high neighborhood crime rate.  If, however, they complain that their water view is spoilt by fireworks every Fourth of July start thinking about what items you might want to list when you create your Crate and Barrel gift registry.
  3. What’s the last book you read? This is one way of finding out if the person you’re speaking with actually reads.  Just asking if they read won’t tell you anything at all.  Anyone can say “yes” to that.  Knowing the book’s title will tell you if a) he or she read anything in the last decade, and b) his or her tastes and affiliations.  For example, if Mr. Perfect responds to the question by telling you that “Breaking Dawn” was the last book he read and that it was so beautiful that it “…made him cry” you may want to change your Net handle and start all over.  If, however, he declares that he has just reread a book from his Michael Cunningham collection then your next question should be if he ever considered moving to Vermont where gay marriage is legal.
  4. Who is someone you would consider a “hero” or role model? Another question designed to give you some insight into his or her character and interests.  If, for example, your own personal Portia di Rossi confesses that her repurposed wooden book shelves made by Fair Trade workers in Guatemala is filled with the works of Julie Bindel then you pretty much have been clued into the fact that a life with “Portia” will be filled with protest marches and the back window of your Subaru coated in PETA, NOW, and Greenpeace stickers.  On the other hand, if she lists Ani DiFranco, Tori Amos, or Melissa Etheridge then hit the dollar store for the discount glow sticks because, baby, you will be going to a lot of concerts!

Healthy Living Index

  1. How often do you work out? Another trick question.  If you ask him or her if they work out, chances are they will say “yes”.  This could mean: “Yes, I’ve worked out this year”…”Yes, I walk at lunch”…or “I jog to the refrigerator to get my Ben and Jerry’s”.  When you ask how often you get a clearer picture of whether or not he or she actually works out.
  2. What is your favorite food? This is one way of screening people for food allergies, vegan or raw food lifestyles.  When you start to hear a lot of “rice” in the response you can jot him or her down as a potential “gluten free” candidate.
  3. Coffee or tea? This question is much like the previous two.  Not only will you have some insight into their commitment to healthy living, but also whether or not you will have yoga and meditation classes in your future.

Interesting Conversation Starters

  1. Do you believe that extra-terrestrial life has visited earth? I like this question because how he or she answers, how in-depth they go in their explanation will also let you in on how deep their personal rabbit hole actually goes.
  2. Who would you rather…? This game should be played early on in a “relationship” because there are no consequences or hurt feelings involved in the answering.
  3. If you could meet any one person in history, who would it be? This is a good ice-breaker question that can be asked right off the bat.  Of course, should names like Genghis Khan, Joseph Stalin, or Adolf Hitler get rattled off you might want to take your laptop to the police station at once!