1. What went wrong between you and your ex?

Interrogating a woman about her previous relationship is never a good idea. Relationships end for a reason. First dates are supposed to be light, a laid-back meeting to see if there’s chemistry. Don’t get too deep and risk scaring her away.

2. If you could change 3 things about yourself, what would you change?

Asking a woman what she would change about herself implies that you don’t like something about her. Women never want to hear that you dislike anything about them. Stay away from negative conversations, and focus on the positive ones.

3. How much money do you make?

Her salary, or yours for that matter, is irrelevant. The purpose of a first date is to get to know each other, not to find out how much is in each other’s wallets. Concentrate on the conversation, not how much money you both have.

4. Do you still talk to your ex?

The past should stay in the past. If she communicates with her ex, it’s not important as of now. Focus on the present.

5. Tell me about your most recent dating experience.

Talking about your last dating experience is really awkward. When a girl is on a date with you, there’s no need to worry about who she went out with last week or even last month.

6. Have you had any plastic surgery?

You might be dying to know how the woman you’re sitting across from looks so amazing, and if she’s had any work done, but now is not the time to ask. Questions about plastic surgery and enhancements are personal. Save those questions for when you really get to know each other.

7. I have a question about what I saw on Google…

Revealing to a woman that you online stalked her in any way is creepy. No need for Google questions on a first date.

8. What size are you?

Asking a woman her waist size is inappropriate, insulting, and offensive. If you like the way she looks, her size shouldn’t matter.

9. What was your GPA?

When you’re over the age of 21, your GPA isn’t important. Being book smart is valuable info to some people, where real-world success matters to others.

10. Where do you see yourself in 5 years?

You never want a date to feel like she’s on an interview. When you ask a woman where she sees herself in 5 years, she’ll most likely feel like she’s being grilled.


Carly Spindel is the Vice President of Janis Spindel Serious Matchmaking Inc. She has seen the matchmaking business firsthand since she was 6 years old. As the daughter of Janis Spindel, Carly has been called mini Janis since she could walk and has learned the inside tricks of the trade from Janis! Carly has been matching her own clients for the past 6 years, and runs Janis’ Express Matchmaking and Junior Matchmaking divisions. You can learn more about Carly and Janis Spindel Serious Matchmaking Inc. at
  1. So if 5 years is out, how should one get at asking a woman about her goals without it coming across as an interview question. Ask about hopes for the future?

  2. No offense, but this applies equally to women asking the questions as well. I get asked #1 all the time; it’s ridiculous.

    They don’t have carte blanche just because they’re female. You should re-work the title and the article to reflect current realities.

  3. In regards to #1 above women have little trouble asking me why I have not been married. And to make it worse for some it doesn’t matter a lick how I respond. She of course has usually been divorced. Why is it she can bore in on why I’ve not been married and me in turn asking why her marriage failed? one of life’s mysteries it seems

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