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awkward datingLet’s face it; first dates can be pretty awkward. You’re sitting across a table from a total stranger, trying to figure out what to talk about. You don’t want your date to feel like it’s an interrogation, but you do want to ask good questions. If you’re stumped as to how to get that conversation going, don’t worry. You’re not alone. Most people are anxious about how to fill the hour-and-a-half of potentially sweaty armpits and uncomfortable silences. I’ve made it easier for you. I’ve composed a list of 10 great dating questions. Each question will help you get to know your date on a deeper level. Then you can make an informed decision as to whether or not you even want to go on a second date:

  1. Where are you from? This reveals more than just a birthplace. It can also uncover a bit about your date’s history and the type of childhood they had. For example, I grew up in Atlanta with a pine forest in my backyard. Playing outside all day with my siblings and neighbors, building forts, and splashing in our creeks, helped shape the creative outdoorsy person I am today.
  2. What is one interesting/surprising thing about yourself that I wouldn’t know just by looking at you? This gives you more insight into their personality and what lies beneath the surface. I like to share that I can still stand on my head. You’d be surprised as to what a person’s secret talent might be. It can reveal their playful or more creative side, which is important information.
  3. What do you do for fun?  This will shed some light as to whether your leisure activities match. Are you a homebody, while she’s into extreme sports? That could end up being a problem in your relationship. It’s not necessarily a deal breaker if your ideas of fun and recreation don’t match up. But it’s a plus if you share common interests.
  4. What are you most proud of? This question reveals the basic values of the person. For example, are they more proud of their financial achievements or their charitable giving? Do they prioritize their children over their yacht? (Okay, that’s a bit extreme, but you get the picture.)
  5. What is your most treasured possession and why? What a person is sentimental about reveals a great deal about his/her personality. Does he treasure that new Harley or the pocket watch that used to belong to his grandfather?
  6. What is your favorite month of the year and why? Does he like to swim in the ocean in the summer or ski the slopes in the winter? Seasonal compatibility can be an important factor in a relationship.
  7. What’s the last book you read/movie you saw? When you discuss what you’re reading and why you liked a book or a movie, you gain further insight into your date’s values and personality.
  8. What is the last trip you took? Travel is a great conversation starter. How much does he/she travel? What kinds of things does your date do when traveling? Does he like to go on organized tours, or does he prefer to explore on his own? This reveals a lot about your date’s personality.
  9. What is the one job in the world that you would love to do if money were no object? This question sheds light on your date’s values and what he/she is passionate about. Is your date doing anything close to that in his job? Is he happy at work? Is she fulfilling her dreams/goals? I prefer to date men who are passionate about something and take action to fulfill their dreams. That’s very sexy to me! How about you?
  10. Who is your favorite singer/band? Do you share musical tastes? While disparate musical taste isn’t a deal breaker, musical preferences do give you information about the personality of your date. Does he like James Taylor and Joni Mitchell? He might be a romantic. Does he prefer Daft Punk? Maybe he’s a bit wild and reckless. If you enjoy going to concerts with your mate, you’ll probably want to have somewhat similar taste in music.

Can you think of another great question to ask on a date? Please share it below.

For more midlife dating advice and a copy of my FREE report, “The Top Three Mistakes Midlife Daters Make (and how to turn them around to find love now)” please click here.

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