170 Questions Not to Ask on a First Date

So you finally mustered up the courage to date someone. Congratulations! Whether it’s your first date ever or just your first date with this person, you want to make sure it goes well. After all, first impressions are everything.

One way to make sure your date goes smoothly is to avoid asking certain questions. Some questions are just too personal for a first date, while others might be perceived as nosy or intrusive.

I have put together a list to get you started. Avoid these topics of conversation at all costs, and you’re sure to have a good time!

Intrusive Personal History Topics

  1. Which parent do you get along with less?
  2. How many times did you fail in school?
  3. Have you ever been arrested?
  4. Did you ever have a drinking problem?
  5. Did you ever struggle with drug addiction?
  6. Have you ever cheated on a partner?
  7. Were you ever fired from a job?
  8. Have you ever gone bankrupt?
  9. Have you ever had an extramarital affair?
  10. Has anyone in your family been convicted of a crime?
  11. Have you ever battled mental health issues?
  12. Do you have any estranged family members?
  13. When was the last time you cried and why?
  14. Have you ever sought therapy or counseling?
  15. What’s the worst thing you’ve ever done?
  16. Who in your life have you disappointed the most?
  17. What’s a secret you’ve never told anyone?

Financial and Career Queries

  1. How much money do you make?
  2. Have you ever hated a boss?
  3. Have you ever quit a job without having a new one lined up?
  4. Do you plan on climbing the corporate ladder?
  5. Have you ever been demoted?
  6. How many days have you called in sick this year?
  7. Have you ever stolen office supplies?
  8. How many jobs have you had in the last five years?
  9. Have you ever been passed over for a promotion?
  10. Do you have any office enemies?
  11. Have you ever run a business into the ground?
  12. Would you ever become a whistleblower?
  13. What’s the most unethical thing you’ve done at work?
  14. Have you ever had a flirtatious relationship with a coworker?
  15. Do you often work overtime?
  16. Have you ever violated a non-disclosure agreement?
  17. How do you handle workplace stress?

Questions About Past Relationships

  1. How many people have you dated?
  2. Why did you break up with your last ex?
  3. Have you ever been dumped?
  4. Have you ever dated someone from your work?
  5. How long did your longest relationship last?
  6. Have any of your relationships ended in a bad way?
  7. Why did your most recent relationship end?
  8. Were you ever in love with two people at the same time?
  9. Have you ever had a rebound relationship?
  10. Have you ever cheated on a partner?
  11. Do you tend to end relationships or are you usually the one being broken up with?
  12. Have you ever broken someone’s heart?
  13. Have you ever had a one-night stand?
  14. Have you ever stayed in a relationship you knew wasn’t right?
  15. Are you friends with any of your exes?
  16. Have you ever been in love before?
  17. What’s your most heartbreaking memory from your previous relationships?

Excessively Sensitive Subjects

  1. What’s your political affiliation?
  2. Have you ever lost someone close to you?
  3. Were you physically or emotionally abused in the past?
  4. What’s the worst part about your life today?
  5. Have you ever felt suicidal?
  6. Do you have an estranged family member?
  7. Have you ever experienced a traumatic event?
  8. Have you ever struggled with an eating disorder?
  9. Have you ever battled severe depression?
  10. How much do you weigh?
  11. How old are you actually?
  12. Have you ever been a victim of discrimination?
  13. Do you have any unresolved arguments with anyone?
  14. What’s your deepest fear?
  15. Have you ever had an abortion?
  16. Do you have any regrets in life?
  17. Were you ever the victim of a violent crime?

Politically-Charged Topics

  1. Who did you vote for in the last election?
  2. What’s your opinion on gun control?
  3. Do you believe in global warming?
  4. What are your views on immigration?
  5. How do you feel about the current president or prime minister?
  6. What’s your position on abortion rights?
  7. Do you support capital punishment?
  8. What political party do you affiliate with?
  9. Do you support the legalization of marijuana?
  10. What are your thoughts on the national debt?
  11. What’s your stance on same-sex marriage?
  12. Are you a feminist?
  13. Do you believe in a universal basic income?
  14. What’s your view on compulsory vaccination?
  15. What do you think about affirmative action?
  16. How do you feel about trans rights?
  17. What’s your view on political correctness?

Physical Appearance Statements

  1. Have you gained weight recently?
  2. Are you going to lose some weight?
  3. Have you considered plastic surgery?
  4. Did you have a nose job?
  5. Do you think you need a makeover?
  6. Do you plan on gaining some muscles?
  7. Why do you dress like that?
  8. Have you ever thought about changing your hairstyle?
  9. Are those wrinkles?
  10. Do you like your eye color?
  11. Are you planning on getting a tattoo?
  12. Do you need more sleep? You seem tired.
  13. What’s your goal weight?
  14. Have you considered orthodontic braces?
  15. Do you worry about losing your hair?
  16. What size are you?
  17. Why don’t you wear more attractive clothes?

Rushing into Future Planning Queries

  1. Do you want to get married?
  2. How many kids do you want to have?
  3. Do you believe in a prenuptial agreement?
  4. Would you like to move abroad in the future?
  5. What are your retirement plans?
  6. Do you save money for a rainy day?
  7. Are you planning to invest in a house soon?
  8. Do you want your parents to live with you when they’re old?
  9. What’s your plan if you lose your job?
  10. How soon do you think we should move in together?
  11. What are your financial goals for the next 10 years?
  12. Do you believe in a joint bank account after marriage?
  13. Do you see a long-term future with me after this date?
  14. Would you ever consider adopting a child?
  15. At what age do you plan on retiring?
  16. Are you looking to start a family in the next 2-3 years?
  17. Do you believe in life after death?

Negative Life Experiences

  1. What’s the worst memory from your childhood?
  2. Have you ever been bullied?
  3. What’s the most traumatic event you’ve experienced?
  4. Do you ever have nightmares?
  5. Have you ever lost a job you loved?
  6. Have you been hospitalized for a long period of time before?
  7. Has anyone close to you ever been convicted of a crime?
  8. Have you ever experienced bankruptcy?
  9. Did you ever face homelessness?
  10. What’s the biggest mistake you’ve made in life?
  11. Have you ever broken off a long-term friendship?
  12. Have you ever lost a loved one?
  13. What’s the most difficult challenge you’ve had to overcome?
  14. Have you ever been in a toxic relationship?
  15. Were you treated poorly in a past job?
  16. Have you been betrayed by someone you trust?
  17. Have you ever lived through a natural disaster?

Off-Limit Health Matters

  1. Do you have any serious illnesses?
  2. Have you ever been tested positive for an STD?
  3. Have you ever had surgery?
  4. Are you on any medication currently?
  5. Have you ever been diagnosed with a mental health disorder?
  6. When was your last visit to a doctor?
  7. Are you psychologically stable?
  8. Do you struggle with weight loss or weight gain?
  9. Have you ever been diagnosed with a chronic disease?
  10. What’s your blood type?
  11. Do you have any allergies I should be aware of?
  12. Are there any genetic diseases in your family?
  13. Do you see a therapist regularly?
  14. Have you ever been hospitalized for a long duration?
  15. Have you ever had a serious accident?
  16. How often do you get a health check-up?
  17. Do you have healthcare insurance?

Unwanted Comparisons with Exes

  1. Do you think I’m better than your ex?
  2. Which one of us do you think is more attractive?
  3. Do I remind you of any of your exes?
  4. Was I your second choice after your ex?
  5. How do I compare to people you’ve dated before?
  6. Do you think your ex was more fun than me?
  7. Am I more understanding than your ex?
  8. Do I kiss better than your ex?
  9. Does your ex look better than me?
  10. Who cooks better, me or your ex?
  11. Do I handle arguments better than your ex?
  12. Would your ex be better in a crisis than me?
  13. Who’s more passionate, me or your ex?
  14. Am I more interesting to talk to than your ex?
  15. Who made you happier, me or your ex?
  16. Do you miss anything about your ex when you’re with me?
  17. How am I different from what you’re used to?

Frequently Asked Questions

How to make a first date not awkward?

To make the first date not awkward, you have to be yourself and keep things light. You don’t want to seem too eager or desperate, so take your time preparing and don’t overthink things. Just relax and have fun!

If you can make your date feel comfortable and relaxed, they’ll be more likely to open up and have a good time. Compliment them, but don’t overdo it, and be yourself. Don’t try to be someone you’re not—that will only lead to trouble. And if things are going well, don’t be afraid to let your date know.

What do men hate on a first date?

One of the things is when the lady tries too hard. Men don’t want a woman who puts on a show for them, they want someone who is themselves.

Another thing men hate is when a woman is too clingy. If the man wants to go home after the date, she shouldn’t get mad and start texting him non-stop.

Finally, men hate it when the lady doesn’t make any effort on the date. If she doesn’t make an effort, why bother?

What do women hate on a first date?

For example, some women do not like it when their date pays too much attention to other women in the room. Other women do not like it when their date is rude or disrespectful. Some women also do not like it when their date constantly talks about themselves or tries to control the date.

Ultimately, many different things can bother a woman on a first date, so it’s important to be aware of what your date might find bothersome.

How long should a first date last?

There is no set time limit on how long a first date should last, but it is generally recommended to keep it short and sweet. This way, you can leave the person wanting more and they will be happy to see you again.

Also, you do not want to stay too long or embarrass the other person. A good rule of thumb is to end the date when you both feel good about it.

What are the red flags on a first date?

Certain signs may indicate a first date may not go well. For example, if the other person is rude to the waitstaff, or makes derogatory comments about other people, this may be a sign that it is not advisable to enter into a relationship with them.

Another warning sign might be that the person is overly needy or demanding, or has difficulty taking “no” for an answer. If any red flags appear on a first date, it is usually best to end things early and move on.

Final Thoughts

The first date is all about getting to know each other without prying into overly personal territory. While we all have insatiable curiosity about our potential partners, we must balance our desire to know them better with respect for their privacy. With this handy guide of questions to avoid, your first date is bound to have a more meaningful, pleasant, and light-hearted conversation.

So, next time you dress up for a first date, remember to put on your sensitivity alongside your best outfit. Here’s to great first dates and even better conversations!

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Jessa Claire is a registered healthcare provider. Music lover. Daydreamer. Thalassophile. Foodie. A hardworking Capricorn. Most days, an incurable empath. An old soul. Down-to-earth. Vibrant. When she's not writing, she can be seen relaxing with headphones on or engrossed in her favorite fan fiction book.