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Ask These 3 First Date Questions To Size A Man Up Fast!

Dating the WRONG guy? … No one has time for that!


Plenty of Experts offer advice about how to best present yourself on a first date. What you should you wear. Whether it's OK to drink ... and if so, what your booze choice or too many drinks says about you. Do you meet up for coffee the first time, or go to dinner? And what about the dreaded movie date — good idea or BAD idea? Yes, it’s daunting.

But the REAL million-dollar question is — How long should you wait before you ask your date the really tough questions?

You know, the questions he'll judge you for that might freak him out and "push him away." For instance:

  • What consequences come from bringing up your ex too soon?
  • What happens if you share your past dramas (and traumas) too soon? And, what if you screwed up your last relationship?
  • What about your dating goals? Do you want to get married? If so, how soon can you say so?

Ohhh, it's all so scary! Right?

Overwhelmingly, men and women DO still want to get married. That means, at some point, you're going to have to tell your guy that marriage is on your mind. The mistake is waiting too long in the hopes that the guy you're dating comes to the realization on his own. 

So, how can you find out faster if your relationship goals are compatible with his? 

By asking a few well-placed questions as early as your first date.

I was tired of dating a new man, wasting weeks and even months trying to figure him out. I knew the qualities I wanted in a man. More importantly, I knew the traits and behaviors that I positively, absolutely refused to tolerate in a relationship. Sitting in front of a man on a first date I wanted to know 3 important things:

  • Does he have the qualities I’m looking for in a man?
  • Is he concealing a girlfriend or a wife?
  • Will his values, lifestyle and aspirations match mine?

I recommend 3 no-nonsense, yet non-threatening questions will help you quickly evaluate a guy.

A man who is dating for the right reasons (and has nothing to hide) is likely to be open to answering your matter-of-fact personal questions. And although these questions are not foolproof (they many not adequately expose a skillful, conning romance artist) they can help you decide whether if a man is worth more of your time and effort.

Question No. 1: When was your last relationship?

This opens the door to: Are you currently dating anyone? You want to know if he recently broke up with a girlfriend (or he is separated from his wife) because (a) he may still be in love with her making him emotionally unavailable, and (b) he might suddenly decide to go back with her leaving you with a broken heart. The second part of this question is: Why did he breakup with his girlfriend (or why did he get a divorce?) Listen carefully to what he says. If he totally blames his ex-girlfriend-wife for the problems in his relationship—get ready for a bumpy ride. Warning: don’t be surprised if a man says, “Oh, I’m not divorced, I’m married” and he’s looking for a fling.

Question No. 2: What qualities are you looking for in a partner?

Pay attention to what a man says because he will often mirror his own qualities. If he says loyalty is important to him in a partner—most likely he will be a loyal, committed partner. This question can also expose his negative traits, e.g.; if he says he won’t do drama, he was most likely a part of the problem. Many a man has blamed his infidelity on his wife, claiming she denied him sex—when in truth he neglected or maltreated his wife and she, in turn, became withdrawn, resentful and non-responsive.

Question No. 3: What do you see yourself doing in five years?

This question can reveal a layer of truths. If he says he wants to travel extensively, ask where? Is he talking about flying to Europe or selling is home and living in a motorhome? Will a home-on-wheels match your lifestyle expectations? If he says his grandchildren are the most important part of his life, can you share him? If he says frequent golf trips with his buddies are a big part of his life, can you be happy at home while he parties-down in Pebble Beach?

I quit dating a retired, good-looking, charismatic, silver-haired hunk because he kept telling me the 3 loves of his life were golf, scotch and cigars. I thought: maybe that’s why his wife left him?

TIP: Listen to what a man says. Watch closer what a man does.


God Please Fix Me! TrilogyNeed a little dating pick-me-up? Nancy specializes in giving women the straight truth about men, and how to date with your head screwed on straight. Her trilogy of books include: God, Please Fix Me!Never Date a Dead Animal and Secrets of the Ultimate Husband Hunter. 

Purchase books HERE! FREE SHIPPING! NEXT DAY Delivery. Available in paperback and eBooks at online stores.

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