Doc Love Dating Advice

                         Women Don't Lie - Men Don't Listen
                               Success Coach - Doc Love

Hello Doc,

I’ve received great benefit from your advice about how to deal with women when they start interrogating you, which of course they often do. Over the past few years I’ve been out with several different women who would pry and probe with very personal questions, even on the first date. I used to get so intimidated by them when they’d start in on me like that, but your coaching has changed the whole paradigm for me. Thank you doc!

I’m writing hoping that you could share more about dealing with this from the other side of the equation. Is it ever a good idea for a man to give his date an intensive quiz of some type? And what would be the crucial things that he should ask her? Are there direct questions that a guy could ask a girl to quickly and easily pre-qualify her, so to speak, and determine if she’s a gold digger or a high-maintenance nut case or a professional dater?

Jerry – who would like a list of questions

Hi Jerry,

Too often, men allow themselves to be pressured and intimidated by women’s confrontational questions. They get flustered and often find themselves putting their foot in their mouth before they know what’s happened. But rather than take the beating, you can take charge. Your date may be coming on like a determined district attorney who will settle only for the truth, the whole truth and nothing but the truth, but that doesn’t mean, guys, that you have to succumb like a guilty school boy.

There are a couple different ways to take control. One is to deflect and redirect the focus of the conversation by using humor. She asks you, “So, have you ever been married?” and you say, “Yes I have. In fact, I’m married now. I have six wives, but I could use one more. Would you like to be number seven? If we leave right now we could be in Vegas in about six hours.”

Another way to deal with the inquisitional pressure is to take the direct approach and fire the probing and provocative inquiries right back at her. She asks you, “So what’s the longest relationship you’ve ever had?” and you say, “Six years, seven months and two and two thirds weeks. How about you? What was your longest relationship?”

Here is a list of the Top Ten questions you can ask your date which will keep her on her toes and also garner you some very useful information. Just, remember. Do not always accept the first answer you get to each of these questions. Often, the truth will only be revealed after you ask more intensive follow up questions to the original. So, don’t be in a hurry to get to the next question on the list. As they say down on the farm, “You’ve got to milk it!”

Also, keep in mind that all women by nature are inquisitive. A woman who is in touch with her femininity and who has a high level of interest in a man will ask him personal questions about himself. She’ll want to draw him out. That’s a good thing. You want her to be curious about you. But you don’t want her to be pressuring you.

So it’s important to learn the distinction between when a woman is being curious versus confrontational. (Often it’s the tone she uses when she asks a particular question that let’s you know which is which.) Save the heaviest and most serious questions on this list (6-10) for those times when your date is being confrontational. Questions 1-5 can be used when she starts asking you provocative questions about relationships but still isn’t trying to put you in the hot seat.

And here’s another important point about communication between the sexes. Women are generally much better listeners than men are. A lot of you guys need to improve your listening skills. As on overall policy, you should be asking your date interesting meaningful questions about herself, questions that you genuinely want to know the answer to. One of the biggest complaints that women have about men is that they go on and on about themselves and hardly ask a date anything about herself.

And one last caveat. HANDLE WITH CARE! Don’t ask any of these questions unless you are also prepared to answer the same or similar ones yourself.


One) What do you think is the biggest mistake that men tend to make in relationships? (This will tell you a lot about what turns her off and also about her attitude towards men in general.)

Two) Do you think that men tend to be too macho or too sensitive?

Three) What are the qualities of your ideal relationship?

Four) Have you ever gone out with a guy who was a Challenge? (Have her describe how he was a Challenge and how she responded to it.)

Five) What’s the most important thing that men don’t understand about women that they should?

Six) Have you ever had your heart broken? (The more beautiful she is, the more likely the answer will be no. It’s actually better if the answer yes. A girl who’s had her heart broken has some humility.)

Seven) What scares you the most about opening your heart to a man?

Eight) Were you usually the dumper or the dumpee in your past breakups?

Nine) Do you feel you’ve ever had a truly successful relationship?

Ten) Why did you’re last relationship fail? (Does she take any responsibility or is it all his fault?)

Remember, guys: when she puts the pressure on, you’ve got to fire back.

To send me your love questions or to find out more about “The System,” visit me at or call (800) 404-2644.    

Doc Love is a talk show host and entertainment speaker who coaches men in his seminars. For the past 30 years he has asked thousands of women, “Why do you stay with one man versus another?”      

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