This might not be important to you, but it might be. Why: The main point here is not to jump to assumptions about your date's politics. Why: If your date is exploring a relationship with someone else you might want to push pause at the end of your first date but offer them the opportunity to get back in touch with you if the other relationship doesn’t work out. Especially in the age of internet dating, people sometimes meet multiple people they’re interested in around the same time.

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Key goals of a first date are to (a) see if you have a connection, and (b) find out if you and your date have any major areas of incompatibility. Why: Does the person have strong feelings or are they more easygoing and with milder feelings.

We’re wired so that once we start to develop an emotional attachment this is hard to break away from. Why: Different vacation preferences or amounts of vacation time can be a major source of ongoing incompatibility. Why: This question helps establish if your date has a positive or negative attitude? Why: Helps you find out the person's preferences and also helps you establish if the person has any free time or if they're a workaholic.

Whether you’re having drinks with the boys or connecting with a girl on a dinner date, personal conversations help you to genuinely understand each other in a profound way.

While heavy discussions can be intense, they’re incredibly rewarding.

Here are some of the best deep conversation topics: If you’re not prepared for a potentially lengthy discussion, you may want to use some of our other deep questions to ask. This question can help both people recognize their blessings and appreciate them more.

Remember: conversation starters give you a topic to work with. Here are 15 of the best deep conversation starters: What’s better — a long life or a life well-lived? How much value do you put on human life as a whole? What’s that life lesson that has stuck with you all these years?One of my favorite flirty questions to ask a girl is this one because it takes the romance and chemistry to the next level.You’re letting her know you’re interested as well as getting some useful information.Find out early if there are reasons that “making it work” will be fraught. Select a few of these questions rather than attempt to ask them all on the same first date! For example, if one person likes to take very long trips and the other person has a more standard two weeks vacation time. If asking this question leads to five solid minutes of them complaining you'll know the person sees the glass as half empty. Why: When you enter a relationship with someone you’re also entering a relationship with their friends. Why: If one of you doesn't like pets and the other has 3 dogs, that's likely to be a problem. Also, if anything out of the ordinary has happened that might be affecting your date’s mood, it’s good to factor this in. Also, it’s nice to give your date an opportunity to answer a question that isn't directly about them. The first couple of dates with a new girl can be awkward, but they’re a lot less awkward when you know the right questions to ask to get the conversation going.