It’s great if you want to get to know your date better, but make sure the conversation is evenly exchanged. No one likes being fed rapid-fire questions. It’s invasive and a huge turnoff.
When you’re having any conversation you should always make sure to gage the interest level of the person you’re speaking to. Don’t get so caught up in what you want to know that you fail to recognize his or her discomfort. Some people are too polite or have a hard time enforcing healthy boundaries, they’ll go along with you in the moment but most likely won’t ever subject themselves to you ever again.
When you’re on a date, make sure that you’re always giving as much information as you’re trying to get. If you find that you’ve already asked too many questions you can turn it around by saying something like, “What would you like to know about me?” A two-sided conversation is much more pleasant to participate in.
Read more about how to recognize bad behavior and how to create a healthy, long-lasting relationship in my book Giving Up Junk-Food Relationships: Recipes for Healthy Choices