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“Got any great first date
questions I can ask?”

When it comes to first date questions, there are things you should ask and questions you absolutely need to avoid. First of all, a first date is nothing more than a job interview to see if he can competently fill the position of being your boyfriend.

It’s a chance to see if he meets your basic requirements and can fit easily into your life.

The questions you ask him say a lot about yourself. If you ask smart and funny questions, he’s more likely to think you are both smart and funny. If you ask the standard interview questions, he might form the opinion that you are much like many other women in his life.

There is a reason he’s not dating them either…

What not to ask on a first date

Your first date questions have a way of exposing your ultimate goals. They also have a way of scaring off a good guy before you get him hooked. The following things are subjects you should definitely avoid:

CAN you be my boyfriend?

  • Marriage and children. unless you guys met at a divorcee group or your child’s play date, keep your goals hidden. By asking about this, you are screaming how badly you want one or both. Don’t believe it? Women who aren’t interested in marriage or children never ask. It’s not part of their reality, so they have no reason to bring it up. It’s the same way that a man will ask you if you like football. He’s only asking you because it’s important to him. Don’t show your cards right away. The marriage/babies issue is definitely an important one, but it comes much further down the road. In fact, an anti commitment guy might find one day that he loves you so much, he'’ll commit to both without blinking an eye. Any good salesperson will tell you never to ask for an important opinion. Once a customer tells you he would never do something, he now has to make that commitment just to keep his word. What if you “sold” him the idea of children over time and show him that he actually likes kids before you tell him you want children?
  • Opinions about troublesome subjects. Don’t bother with these first date questions especially if you feel very strongly about them. Everyone has an opinion about abortion and war and religion and drugs and the homeless. If his answer is opposite of yours and it will upset you, just don’t do it.
  • His ex-girlfriends. He might actually offer this information himself, but if he doesn’t, don’t go there. It shows you might be the jealous type and it’s a little too heavy for first date conversation.
  • His job or possessions or cars. What? I can’t ask about what he does? Everyone asks that question! Precisely! By adding the standard resume quiz to your first date questions, you make yourself look like every other girl he’s ever gone out with. The great thing about this is he has a standard answer for these kinds of questions. He will be confused that he doesn’t get to brag about himself or his house or his car. It throws a fella for a loop. Obviously, you’ll get this information later. In fact, he’ll often offer it without you asking. This gives you an opportunity to joke with him about bragging.

Great first date questions

Ask him crazy things. You want to get him thinking. You want to see how well he thinks on his toes. You want to give him a great experience too. What could be more fun than talking about yourself all night and thinking deep thoughts about silly stuff. Believe it, he’ll call you for the next date and will definitely mention how much fun he had.

If you're here because you need some questions for tonight, we suggest you read the awesome book, 1000 Questions for Couples. It's packed with a busload of great thoughts and questions to really get into someone's head. The best part about this book is that it's an eBook. You can download it now and have a thousand first date questions for tonight!

  • ”Would you rather” questions. “Would you rather spend a year sailing around the world or helping starving children in a far away land?”… There are a million different scenario choices you can pose to him. The awesome thing about these questions is that you get to find out what he values the most and how that compares to your values. If you want your boyfriend to be Earth friendly, make an ecological answer for one of his choices. If you want him to be active, give him a choice of being a nobel prize winner or a star athlete. If you really want to breach one of the off-limit questions above, you can disguise them with this method: “Would you rather have a bunch of kids and start a band like the Jackson 5 or would you rather coach a volleyball team made up of all your ex-girlfriends?” Brilliant…
  • The “if” question. If you had a million dollars and had to spend it in a month, what would you do? The if questions are a bunch of fun and really give you insight on how he thinks. “If you were stranded on a desert island and there were four famous or historical people there, who would you pick?”
  • Best childhood memories. Do you want him to think good thoughts and associate those feelings to you? Ask him about super-happy times for your first date questions. Make sure to give him approving statements and maybe touch his arm when you make your comments. You can bust this one out whenever the conversation gets weird or slow.

Have an answer

There is a great possibility that he will ask the same questions back at you. Make sure you have just as interesting an answer. If you really need to brag about yourself, ask him questions that you want to answer. For example, if you want to talk about how much you travel without sounding conceited, ask him where his favorite vacation spot is. After he answers, it’s your turn to dazzle him.

Even if everything else is boring about the first date, you can always make yourself memorable with some great first date questions. Remember your goal is not only to find out who he really is, you also need to make a great first impression yourself.

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