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10 Questions to cure a quiet moment on a date

Is fear of awkward silence putting a damper on your dating? We asked dating experts how to keep the conversation flowing. Here are ten fun and flirty questions to try on your next date.

Couple on date sharing a milk shake

Create a question cheat sheet

We asked dating and relationship expert Julie Spira, founder of and author of the bestseller The Perils of Cyber-Dating, how to banish those quiet moments when you just don’t know what to say to your date. Her advice? Lighten up. “No one wants a date to feel like an interview or a deposition. It’s an instant buzz-kill to be interrogated, so I recommend a cheat-sheet of questions to talk about that make your dating conversation fun.”

Get started with open-ended questions:

  • Where did you go on your last vacation? What did you enjoy about it?
  • Where would your dream trip be if someone gave you a free airline ticket to go anywhere?
  • Do you remember your first rock concert? Are there any bands on your wish list that you’d like to see?
  • If someone gave you $1 million to donate to charities, which ones would you select?
  • Do you prefer lazy weekends at home doing a crossword puzzle and reading a book, or do you prefer going out hiking and biking?
  • Has anyone ever told you that you look like a celebrity? Who do you think would be your celebrity look-alike?

Get the goods on “taboo” subjects

Amber Soletti, dating expert/matchmaker and co-founder of two popular NYC dating services OnSpeedDating.Com and SingleAndTheCity.Com, has observed thousands of singles go on first dates. “Through years of dating and observing daters I’ve been able to really gauge what works and what to avoid when it comes to conversation.”

“Life is too short for there to be taboo ‘first-date’ subjects,” says Soletti. “I say put it all out there so as not to waste time. Talk about topics of substance. Politics, religion, sexual preferences, everything you were always told not to talk about on a first date are the conversations which will really enable you to see if you’re going to be compatible with and potentially connect with a person in the long run. Why wait till the third or fourth date to find out that you don’t see eye to eye on major, ‘deal-breaker’ topics?”

Rather than sticking to the basic, run-of-the-mill “Where are you from? What do you do, Where do you live?” line of questioning, Soletti suggests mixing it up with open-ended, fun, flirty questions that allow you to gain more depth and understanding of your date.

Spice up your cheat sheet with questions like:

  • Who is your celebrity crush?
  • If you could only eat at one restaurant for the rest of your life, what would it be?
  • What would (or wouldn’t) you do for a million dollars?
  • If your date is a big movie buff or geography guru, rather than just talking about the subject, turn it into a game. Do you like movies? Have you ever played the movie game? (Pick an actor/actress and go back and forth naming movies until one of you can’t come up with one.)

“A little competition is healthy for a relationship, especially a new one,” says Soletti. “It will help you gauge how smart, creative, competitive, collaborative and most importantly, what type of winner or loser your date is. It also creates the good type of ‘sexual tension’ that will secure you a second date.”

Tell us

Do you have go-to questions you like to ask your dates to spice up the date? Tell us in the comment section below.

More dating tips

Body language that signals “I want this date to last longer”
5 Ways to ask for what you need in your relationship
Not a good conversationalist? Here’s how you can improve

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