How To Learn Something New And Interesting About Your Significant Other (Hint: Ask Thought-Provoking Questions!)

categories: Date Idea, How To:, Romantic Ideas

It’s safe to say that I know Olga better than just about anyone. I know what she likes, what she doesn’t like, what makes her tick, and the values she embraces. And I’m sure you probably feel the same way about your significant other. That said, Olga and I had a date the other night where we probably learned more about each other over the course of a few hours than we did in all of 2011.

We actually weren’t even planning on filming a blog video about the date, but it was so amazing that we wanted to share with all of you. It’s about as simple a date as you could imagine: having a thought-provoking conversation about life, goals, and dreams. And the best part is that you can have this date anywhere — on a nice walk (like Olga and I had in the video above), over a glass of wine, or just cuddling on the couch.

Of course, the most difficult part of having a thought-provoking conversation is coming up with the thought-provoking questions to jumpstart your discussion. Well, I’ve got great news for you. Marc and Angel over at the Marc and Angel Hack Life blog have done all the work for you! I came across their blog a few days ago when I saw a number of friends on Facebook sharing their fantastic piece on “30 Things To Stop Doing To Yourself”, which I highly recommend you check out (if you need social proof that the content rocks, this single post has over 265,000 likes on Facebook!). A quick warning though… if you go to this blog, you will likely get stuck there for quite some time reading article after article. I ended up exploring for a few hours, during which time I came across the following posts:

I was so intrigued by the questions (and what Olga’s answers would be!), that I decided to make a date out of it.  I picked out 20 of the questions that I was most interested in (I could have picked more, but I’ll save those for a later date). I then copied and pasted them into an email and sent them to myself. Next, we headed to Palos Verdes to enjoy a nice romantic stroll along the coast leading up to sunset.  During our walk, we simply went through the questions together and an amazing conversation ensued. To give you a taste of the questions we discussed, I’m listing a handful below (but I would suggest you visit the links above to find the questions you’d be most interested in discussing).

  • If the average human life span was 40 years, how would you live your life differently?
  • If you could offer a newborn child only one piece of advice, what would it be?
  • What one thing have you not done that you really want to do? What’s holding you back?
  • What’s your single greatest moment of personal failure? Looking back on it now, did it make you weaker or stronger? What did you learn?
  • What will be different about your life in exactly one year?
  • How old would you be if you didn’t know how old you are?

Both Olga and I were pleasantly surprised to find out that, although we know each other incredibly well, we still have so many interesting things to discover about each other.  We highly recommend that you try this date for yourself, and check out the Marc And Angel blog when you have a moment.  You won’t regret it!

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  • Jill

    Great date idea. And thanks for the tip on the Marc And Angel blog. I checked it out, and like you said, got stuck there for hours. What a great resource! Merry Christmas


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