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I asked a single friend of mine what his strategy is for asking questions on a first date. He agreed it is best to first consider what questions should NOT be asked. It's simpler to get those out of the way before discussing what question can be asked. There definitely are some areas that are not suitable for exploration on a first date:
1. Don't ask how many former relationships your date has had. This information will be volunteered, most likely, at a later time. On a first date, it's personal information.
2. Save involved questions about childhood issues until later. These questions are not addressed until much further along in a friendship or relationship.
3. Don't inquire about how much money your date is making. This is none of your business on a first date. You'll have some clue when you find out what he or she does for a living.
4. Don't ask about sexual habits or history, STD's, or anything really personal. You may find yourself on a very short date.
5. Resist the temptation to ask any questions that put your date "on the spot" or make him or her feel uncomfortable. Uneasiness is a feeling that will make this your one and only date with that person.
6. Avoid religion and politics like the plague. Even if you are sure you're both on the same page, the slightest difference of opinion could derail the whole experience and eliminate the possibility of a second date.
To consider what questions can appropriately be asked, there are several that are completely within the boundaries of good taste and will give you some insight into the person you're dating:
1. It's usually safe to discuss the basics. Where were you born, and where did you grow up? Where did you go to school? What do you do for a living? You may know some of this basic information from earlier conversations, but you can go over it to get more details. People usually like to talk about these subjects. Still students? These questions can be adapted to your phase of life.
2. You can ask about parents; for example, are they still living? Do you have siblings? Large family, or small? Happiest memories? Favorite vacation places and memories? Favorite season of the year and why? Any favorite memories from childhood are good subjects for discussion. Conversations may naturally go this direction without questions.
3. It's okay to ask questions that indicate what your date sees for himself or herself in a couple of years. You can get a sense of what your date is looking
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Questions to ask on a first date
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