Again, when that point is will depend on you and what you think the other person is ready to respond to.
You may consider making a list and have them answer the ones they are able to answer.
w=1024" class="wp-image-346491 size-full" src="https://scstylecaster.files.wordpress.com/2015/03/crazy-stupid-love-movie-image-ryan-gosling-emma-stone-02.jpg? w=1024&h=683" alt="first date questions" width="1024" height="683" srcset="https://scstylecaster.files.wordpress.com/2015/03/crazy-stupid-love-movie-image-ryan-gosling-emma-stone-02.jpg? Have you traveled anywhere cool lately/do you have any trips coming up? Some of these questions may seem silly at first, but they can be very telling.
A foolproof way to ensure that conversation will always be flowing is to simply your date things, although—given the fact that we never know how comfortable others are with casual conversation—that might be easier said than done. Where exactly do you live in [insert your city or town here]? Questions over the first drink should be an equal mix of inquisitive and casual, and should allow you to start gauging his or her true personality.
Do you have a criminal record, any contraction of diseases?
Dating is all about having fun, but at some point if you do find yourself with someone that you are thinking of maybe having something a little more long term; there are certain topics you should cover.
You will save yourself and them a lot of everything if you talk about these things at some point. Where do you consider good places for a couple to be romantic?
Time to seal the deal—the last few minutes of a date are crucial to make sure a second date happen.
Do you have any fun plans for the rest of the weekend?
The trick to successfully vetting a prospect on a first date, while simultaneously keeping the energy light and fun, is knowing what questions to ask and how to ask them. What are their likes and dislikes, what do you have in common, what does he or she do in their spare time?