1. What’s your favorite scene from your favorite book or movie?
Talking about mass media and pop culture can clue you in to similar interests and worldviews. “Books, movies, and music all transmit powerful messages of hope or emotion,” says Hogan. “If you have radically different preferences, there may be some fundamental differences between the way the two of you look at the world.” But asking your date to name his or her favorite scene can help you distill what’s important to him or her beyond just genre.
2. What do you love about your job?
The standard, “What do you do?” is a closed question that doesn’t reveal much about a person other than a job title. But if you phrase the career question a bit differently, you can delve into your date’s likes and dislikes; reveal his or her strengths; see how he or she handles conflict; and find out how happy this person is with life overall. Think about the different impressions you’ll form if your date answers the question, “Knowing that I’m helping people fulfill their dream” versus “Deciding what to order for lunch!”
3. What’s your definition of a relationship?
Granted, it takes a bit of build-up to ask this question (usually, once you begin discussing your dating histories, you can slip this one in), but it’s worth asking. Does your date want to be wined and dined, or are you both looking for a 50/50 relationship? It’s too soon to know what this specific potential relationship will look like, but a question like this lets you share your expectations and fundamental beliefs. “I like to ask this question early on, because I’ve found that some women I’ve dated didn’t know what they wanted out of our relationship,” says Mario Webb of Ft. Walton Beach, FL. “They came into it just hoping things work out without telling me what they expect. Needless to say, things haven’t worked out.” And if your date’s answer is outside the range of what you consider acceptable, you’ve saved yourself future heartbreak by finding out before you fall for him or her.
4. If money were no object, what would you do with your life?
This tried-and-true icebreaker showcases your date’s hopes, dreams, and regrets — topics that often remain untouched by even serious romantic partners. The answers can range from a desire to travel to going back to school to learning how to play the violin. Two buttoned-up stockbrokers might discover they both share a secret longing to be athletes or a shared devotion to public service. Your date’s response will help clue you in to common goals and interests that go beyond what you do on a day-to-day basis.
5. Will you share an embarrassing moment with me?
This fun question is great to ask when a date has gotten a little tense or quiet, because it reveals both details of your date’s history and his or her character. Just know that you may have to share an awkward experience first in order to make your date feel comfortable. “One of the great things is that our humanity is a bonding thing,” says Hogan. “Our ability to laugh at ourselves is critical in a budding relationship.” So make it clear that you’re not looking for dirt on that plagiarism incident in 11th grade, but rather something goofy, like the time you drove a golf cart into the water, installed a chandelier upside-down and so forth.
By asking these questions and considering the answers, you’ll gain valuable insights onto your date — and know whether the two of you are likely to click on future get-togethers.