3 Questions To Ask On A First Date (To Figure Out How Compatible You Truly Are)

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questions to ask on a first date

I was tired of dating a new man and wasting weeks, 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 upfront a few important things: Does he have the qualities I’m looking for in a man? Is he concealing a girlfriend or a wife? Do his lifestyle and aspirations match mine?

RELATED: 20 Intimate Questions To Ask A Guy To Really Get To Know Him

So I came up with three good questions to ask on a first date that will help you to quickly evaluate any man. Although they're not foolproof — they may or may not adequately expose a skillful, conning romance artist — these first date questions can help you decide whether a man is worthy of your valuable dating time and effort.

I asked my future husband these three questions on our first date. He was a little taken back at first by my directness, but he answered them with such sincerity that I decided he was worth a second date. I married him a year and a half later.

For your benefit, here are my three essential questions to ask on a first date.

1. When was your last relationship?

This opens the door to: Are you currently dating anyone? You definitely want to know if he recently broke up with a girlfriend (or if he's separated from his wife) because a) he may still be in love with her, making him emotionally unavailable to you, and b) he might suddenly decide to get back together 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 that relationship — get ready for a bumpy ride. 

RELATED: The #1 Thing Men Do On A First Date That Immediately Turns Women OFF

2. What qualities are you looking for in a partner?

Pay attention to how a man answers 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 intimacy, when in truth he neglected or mistreated his wife and she, in turn, became withdrawn, resentful, and non-responsive.

3. What do you see yourself doing in five years?

This question can reveal layers of truths. If he says he wants to travel extensively, ask where. Is he talking about flying to Europe or selling his home and living full-time 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, are you willing to 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?

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

RELATED: 5 Amazing First Date Ideas That Are WAY Better Than Dinner And A Movie

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If you’re newly divorced or you keep dating and falling in love with the wrong man you will enjoy reading "Never Date a Dead Animal: The Red Flags of Losers, Abusers, Cheaters, and Con-Artists."

This article was originally published at Know It All Nancy. Reprinted with permission from the author.