Five Good Conversation Questions for Dating

One of the biggest obstacles to having an appealing date, particularly with someone you don’t know well, is finding that level of conversation with which you’re both comfortable. If you’re one of those people who isn’t good at coming up with topics off the top of your head, here are a few guaranteed conversation starters. Remember one thing, however. While these questions are good for the course of the date, a way to keep the silence from becoming overwhelming, they should never be put forth in an interrogation style. This is one of the number one turn offs for both men and women. Let the questions come naturally, and follow their answers into interesting and unique conversational pathways. Don’t just sit there and rapid fire questions as if you’re doing a profile for the newspaper.

With that out of the way, here are five good conversation questions for dating. They will enrich your date, and help you to get to know the woman (or man) sitting across from you at the restaurant. After all, getting to know each other and having a good time is what dating is all about. Don’t feel obligated to stick to the questions, one by one, and verbatim. Let them instead spark ideas in your own mind, and don’t hesitate to tailor them to your own personality and to the personality of your date.

Question #1: Tell me a little about growing up in ___________.

This is a great question that can follow the discovery of where your date was born. It allows them to talk about themselves, and it gives them a chance to talk about a time a lot of people enjoy talking about: their childhoods. What’s even better: talking about childhood makes people feel closer to their companion. It associates you with their memories of telling these stories. It fabricates a sense of familiarity. That’s always a good thing.

Question #2: If you could choose anywhere to live, where would it be?

This is another great question, for different reasons. It allows the other person to expound on their fantasies, which are always some of the happiest thoughts a person has. In sharing them with you, they once again make a subtle and subconscious association. They associate those happy feelings with talking to you.

Question #3: If you won the lottery, what would you do/buy?

Once again working on the fantasy psychology. But beyond that, it’s just a fun question, and it should lead to some interesting conversational avenues.

Question #4: What is your favorite movie?

If you like talking about films, this is one of the easiest ways to get the conversation turned into that direction. One important thing to note: remember your manners during this and all other part of the conversations. It’s okay to pretend to be tolerant of, or even like movies that you don’t really care for in order to foster a connection. The date isn’t about movies, after all, it’s about making a love connection. Don’t forget that.

Question #5: If you were stranded on a desert island…?

Of course, we’ve all been asked this question, in all its many forms, so use sparingly. But it offers up a fun way to ask about all manner of interests and favorites. It’s a great way to start up a good conversation and a good way to fill the silence if it begins to weave its web around you. Just remember, the date isn’t about playing a game, it’s about getting to know each other, so don’t hesitate to go off into tangents.

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Jonathon Locke


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