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20 Questions To Ask On a First Date( From a Woman’s Perspective)

First dates can be awkward. There are so many unknowns, and sometimes it’s just hard to know what to say. Not only are you trying to find out more about your date, but you’re trying to make sure you make a good impression yourself.

Both people should be relaxed, but not too relaxed. You want to show you’re interested and ask some good first date questions. On the other hand, you don’t want to ask too much too soon. There’s so much to think about!

If you’re wondering what’s appropriate for those first date questions, keep on reading! Grab your pencils because this is written from a girl’s perspective.

Conversation Starters

first date

Here are some light first date questions you can ask at the beginning of your date. They are also good if you will be riding in the car together. These are general conversation questions that wouldn’t seem too forward or out of the blue to ask.

  1. Where did you grow up? Did you like it?
  2. What do you do for a living? Do you enjoy it? How did you become interested in that position? Is there a different career you’d like to have?
  3. What are some of your hobbies? Who do you like to do them with? What do you like to do on the weekends?
  4. What kind of music do you like? Who is your favorite artist or band? Who did you like as a kid?
  5. Do you have any pets? Did you have any growing up?

Questions To Get To Know Your Date

first date

The first couple of dates are all about getting to know each other past the cliché, small talk questions. The goal is to ask a question that will freely ease into more discussion. Here are a few examples of questions to ask:

  1. Are you enjoying your food? What is your favorite kind of food? Do you like to cook?
  2. Did you play any sports or instruments as a kid? Do you still play?
  3. What was your favorite movie or TV show as a kid? Do you have a favorite now?
  4. Do you watch any sports? What is your favorite team?
  5. What is your favorite time of the year?
  6. Are you close to your family? Do you have any siblings? Are you an aunt?
  7. Do you have a nickname? Is there a story behind it?
  8. Do you like to travel? Where have you traveled? Is there a place you’d like to travel to? What’s your favorite way to travel? Have you learned anything from your travels?
  9. Where do you feel most relaxed? Why?
  10. Who has influenced you the most in your life? Why?
  11. Who do you admire? Why?
  12. What is an interesting fact about you that is unique to you?
  13. Do you have any pet peeves?
  14. What is one thing you’ve always wanted to try?
  15. Is there anything you feel I should know about you?

Note: Do not ask all of these questions. No one wants to feel like they are being drilled or interviewed. These are just sample questions. Remember, the goal is to ask some questions to branch off into deeper conversations. Do not keep a list of questions anywhere as that can come off as tacky.

Ask Follow-up Questions

first date

People love to know they’re being listened to. They want to know their opinion and thoughts matter to you. Listen to what your date is saying and then ask questions about what they just said. They don’t have to be any specific kind of questions, just ones that show you were paying attention.

Other Things To Do On The First Date

first date

  • Ask “where to?” Prepare a few date places in the back of your mind, but ask where she would like to go when you pick her up. This allows you to find out what she likes to do and gives you something to talk about to help ease those first awkward moments. However, this would not work with every woman. Personally, I would not enjoy this because of the pressure to make a decision. Other women may not like it because they may not feel special if the man didn’t have a romantic plan. But, if you think this could be a good move, go right ahead. There are plenty of women who love to help choose plans and voice their opinion.
  • Look at her! Keep good eye contact in a respectful, non-creepy way.
  • Laugh when your date laughs, but not in an obvious, forced way. Women feel more connected to their date when they are laughing together.
  • Make sure you talk about yourself too! Think of the conversation as a tennis match-you both should be bouncing the ball back and forth and no one should hog the ball! If there does happen to be a ball hog, let it be your date and not you!
  • Read her body language! If you bring up a topic that appears to make your date uncomfortable, switch the subject or say, “we don’t have to talk about that.” Studies show that much of communication is from our body language.
  • Speak up! If you feel uncomfortable about something your date did, it is okay to speak up. There needs to be mutual respect, and this could be a clear way to see how the relationship will work.
  • Offer to pay for the meal or activity but do not force it if she wants to pay for herself.
  • Be polite and say “thanks for a good time,” even if you didn’t enjoy the date.
  • If you are interested in another date, ask “can I call you?” This simple question gives her the freedom to decide and lets her know that you’re interested.

Do Not:

  • Talk about past relationships. If you move beyond the first date, past relationships will come up. But talking about your ex (either positively or negatively) is never a good sign on the first date. You will either come across as a jerk or that you are not over her.
  • Be an open book. Just as you do not want to ask your date anything too personal, be sure you are not revealing too much too soon. Doing so is a turn-off and can give the impression that you are self-centered, immature, have unresolved issues, or are emotionally unhealthy.
  • Talk about politics. A first date is no place for a heated discussion on some controversial issues.
  • Bring up anything sexual, not even as a joke. Everyone’s sexual desires are deeply personal and intimate. They should not be shared until you both feel comfortable with each other, which will most likely not be the first date.
  • Ask about marriage, life plans, or future children. It puts too much pressure on the first date. Keep topics light.
  • Ask how old your date is. Some women just flat out hate this question. You’ll find out eventually, so there is no need to ask right away.
  • Ask to borrow money. Or ask how much money your date makes.
  • Come across as desperate. There is no need to discuss marriage at all, even if you are just talking about your own desires. Avoid saying statements such as “I wish I would have met you sooner.” Or asking “where have you been all my life?”
  • Try to “one-up” your date with a better story or funnier joke. At the same time, do not talk negatively about yourself. Both are self-centered. Be humble and polite.
  • Insult your date, even if you’re joking. It’s too soon to know what kinds of comments will be taken lightly, so it’s best to avoid joking in this way at all.
  • Lie. Dating is about finding a compatible person, not putting on the best show. Be yourself and be honest.
  • Keep looking at your phone. If you are waiting for an emergency call or text, let your date know beforehand. Otherwise, put it away.

Now that you’ve read some great first date questions, commit to learning several of them so that you can easily ask from memory.

First dates are always interesting, in that they can end up as a funny story or the beginning of a happy ending. Try not to be nervous and just be yourself.

Happy dating!


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