How to Ask the Hard Questions

In the online world, there is no opportunity to gather information about a person naturally, as you would with someone you go to school with or work beside. Instead, you have to learn about your prospective date purposefully, by asking some pretty direct questions. Because of the anonymous nature of online dating, there is room for intimacy and freedom of expression in both asking and answering questions. But this same anonymity can lead to misunderstanding and hurt feelings, not to mention plain old bad manners. What are the right questions to ask, and how can you pose them in a way that takes advantage of the freedom and opportunity of online dating, yet does not appear rude?

The three sets of questions that follow are designed to walk you through the initial phases of online dating with integrity and openheartedness—and to encourage the same in your potential partner.

The first is a list of question to ask your potential date to decide whether or not you’d like to meet. They are meant to establish any non-negotiable social, financial, or spiritual/religious issues that, if you knew them in advance, would prevent you from going out with this person in the first place. Although most online dating services ask about these areas already, it’s still good to address them a bit more deeply when you know the issue is particularly meaningful for you.

The second focuses on questions to ask on a first date. These are much more playful and fun! Now that you’ve gotten the hard stuff out of the way, you can focus on getting to know each other and discussing individual priorities, joys, and sorrows.

The third continues in the “getting to know you” vein, but focuses specifically on spirituality, whether or not it is attached to a particular religion. No matter how specific or vague, doctrinal or individualistic, most people have a personal view of things like compassion, the nature of the divine, and even the purpose of life. These questions are designed to provoke conversation on these fascinating topics and allow you to get to know the inner man or woman, beyond appearances.

At the end of each set of questions, you should know whether or not you’d like to continue exploring a relationship with this person. I’ll provide simple suggestions for how to communicate that you want to take it to the next level—or not.

Remember--outside of your gateway issues, disagreeing on answers to hard questions is not a sign that the relationship can’t work. You could disagree on everything and still find each other irresistible. Or you could have perfectly matched answers, yet find dating to be a giant snooze-fest. So don’t misinterpret mismatched answers as a sign of incompatibility. Stay open just a little bit beyond your comfort zone. You never know what can happen when you’re open to a genuine dialogue.

Continued on page 2: What to ask in those first emails... »