Eight Great Questions to Ask on a First Date

So, you’re about to go on a first date? With more Americans utilizing the internet to meet their match, what do you talk about on a first date? Haven’t you already asked and answered all the questions on your profile and/or in email exchanges, chat sessions, texting, phone calls? Not even close. You’re looking for a real, honest connection in the face to face. Many people grapple with the realization that “real, live” dating isn’t any easier just because you got to know someone online. 

So here are some revealing and interesting questions to help you out on your first date. They’re not presented in any particular order and aren’t the only good questions you can ask. They’re designed to expose compatibilities and in-compatibilities without being rude or annoying. They’re casual, easy questions that, if used properly, give you a lot of information about the other person.

When you ask questions, remember, you aren’t looking for only the simple one line literal answer to the question. You are trying to provoke a conversation that lets the other person tell you about their self. In that spirit, remember to listen carefully, and ask follow up questions to keep the conversation flowing. Look at it as an opportunity to share common ideas, or even to give one another a friendly challenge. But do not try to compete or out brag one another. That would be a waste of opportunity.

1. Do you like roller coasters?
People who like roller coasters tend to like sensation and excitement. They’re probably willing to take some risks. When you ask if they like coasters, no matter what they answer, ask them why. Get them to talk. If you don’t like roller coasters, and they do, chances are, they’re going to always make you feel uncomfortable. They’ll seem pushy and challenging. If you do like roller coasters and they don’t, there’s a good chance you’ll find them dull and boring.

2. What do you notice right now?
This question may surprise people, and they’ll ask what you mean. The question is designed to provoke their attention, so you’ll need to follow up. Ask if they’re willing to play a game. If they’re not, they are probably pretty difficult to get along with. That’s important info. If they say yes, ask them to close their eyes and tell you what they hear. Get them to reach for every subtle nuance, every bird, cricket, whisper, and sigh.

As they start to get into it, ask them what they feel. Their clothes, the chair, air moving on their skin. You’re only trying to find out how sensitive and aware they are, and how willing to play along and engage deeply with you. Why do you want this information? Two reasons. First, if they’re good at paying attention and connecting to their awareness, chances are they’re very responsible—they’re less likely to be clumsy and careless, more likely to tend toward success in life. Second, it indicates how they will be sexually. Will they have a tendency to connect and share sensual pleasure, or are they bothered by details and sensation.

3. What would you say if I said “sex”?
This may seem risqué, but think about it for a minute. You’re NOT asking them to have sex with you. You’re seeing how they react to the word “sex.” You’re finding out their ideas about sex. Do they get offended? Do they assume you’ve just asked them to have sex with you (because you have NOT). Do they feel it’s creepy or embarrassing?

Or do they find it amusing and bold? Are they willing to talk about sex without getting creepy and weird, and without making false assumptions? Can they become flirty but not come across awkward, overbearing, or weird?

If you time it right, this can be the most powerful and liberating question you can ask. It clears the air. You’ve probably been thinking about sex anyway, so this breaks the tension and lets you talk about it, and have fun with it. It shouldn’t be the first question you ask, and you should pay attention to whether you have chemistry with this person or not. Don’t ask this if there’s really no spark. But if you feel that subtle tension of chemistry, break the tension and have a conversation.

9 readers liked this story.
From Around the Web:
02.24.2010
Janet Madsen
I think this is great- a lovely balance of serious and whimsical questions. Great point on question #3 about sex: it's not a competition about specific sexual experiences, but an exploration about how sexual communication might go: the safe sex talk, the birth control talk (if applicable), etc.
It feels good to write.

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