Root Out The Red Flags: Important Questions To Ask During A First Date

Nothing is more anxiety-inducing than a first date. What could be more nerve-wracking than being all alone with that hunk you’ve had a crush on for ages?

So we spend inordinate amounts of time figuring out what we are going to wear, and worrying about making a good impression when we should in fact be preparing to discover if he is worthy to be part of our lives.

How many times do we come to the end of a relationship and think “I should have seen that coming”, or “He said such-and-such right at the beginning and I didn’t pick it up.” It’s time we started noticing those red flags and asking the right questions.

Interrogation Time


Start by thinking of that first date as a job interview, and you’re the one doing the interviewing. So take a page from smart human resource experts and draw up a list of questions to draw out the information you need. Then find ways to subtly work your questions into the conversation.

Sometimes the best way to elicit information is to volunteer something about yourself. For example (if pets are important to you) tell a story about your first dog, and LISTEN to the response. Another animal lover will share his own funny pet story, someone who is not keen on pets will listen, smile, and move the conversation along.

Question 1 – How Close Is He To His Family?


This is a big one, girls. If he is supportive of his family, he is probably a kind, dependable man. If he adores his mother, he will respect other women.

Of course, this is presuming his family is not dysfunctional… BTW, loving his mom is not a plus if he calls her from the restaurant for advice on what to order for dessert.

Question 2 – What Are His Political Ideals?


This question is all about his core values, things you might not think are important since he’s so hot, but might become giant issues later on in the relationship. Is he a conservative or a liberal?

Will he play nice while you’re dating and then expect you to stay home raising the children so you don’t steal “a man’s job”? Will he be there by your side when you march for reproductive rights and the environment or will he be too busy attending the latest Aryan Nation rally? Ask!

Question 3 – Does He Have A Best Friend


This is another biggie. The sexy loner is a fictional character invented for Clint Eastwood movies. Forget it. A man with a best friend can sustain a long term, intimate relationship, which is great news. The second part of the question is just as important: “Tell me all about him/her…”

Yes, sometimes the best friend is a her, and that can be complicated, too. If you pick up a hint that his friendship dynamics are less than healthy (he is subservient or domineering) bow out. You want a man who wants an equal, anything else is a giant red flag.

Question 4 – What Is His Greatest Achievement


This question will reveal what the man’s true priorities are. He may tell you he puts family first, but if he counts scoring a profit on the stock exchange as his greatest achievement, he is a-lying to you.

This man is more materialistic than emotional, and he will rate your worth accordingly — not by your qualities and talents, but by how much (money/ status) you will bring into the relationship.

Question 5 – What Is He Looking For?


And this is where most of us choose to ignore the red flags! Men will generally tell you what they want, and it’s usually in a subtle (for them) way. Ever heard “I’m still working on closure”? That means in man-speak that he is still having break-up sex with his ex, but is more than willing to give it a go with you too. A man who feverishly grasps your hand and whispers that he is looking for the mother of his children is also not a good bet.

The true secret to picking up on red flags? Listen to what he says, not what you want to hear; and take note of how carefully he listens to YOU. A man who is genuinely interested in you will draw you out, engage in a conversation that is all about you — not himself.

In Closing


Most women go into every first date with unreasonable expectations, ready and willing to hang all their hopes and fantasies on that one man they hardly know.

Most men, a very honest man-friend once told me, don’t expect (or want) every first date to end in a fairytale romance — not even the nicest, best-intentioned ones. They hope it will be fun, will lead to sex, and if everything goes well, they take it one day at a time. So go out on that date, take it easy, have fun…and pay attention!

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