A First Date! Ask these 5 questions.

Every woman needs to ask questions before the FIRST DATE.

Yes, you read that correctly — BEFORE the first date.

And though there are many other blog posts about what questions to ask ON a FIRST DATE, it’s important to investigate him a little before you even bother with the first date.


Because your time is too valuable to waste on Mr. Wrong.

Why waste time going on a first date with Mr. Wrong when Mr. SoulMate is waiting for you!Click To Tweet

Too many times women actually go on the first date without having ruled out Mr. Wrong.

Yeah, it’s exciting to go on a first date!

You get all dressed up.

You stare into the mirror thinking of how wonderful the date could be.

You are full of anticipation.

Your soul is excited.

You’re filled with hope.

You want to be open-minded.

Yeah, THIS guy COULD actually be the ONE!

Lots of pressure on that first date.

Let’s slow down, ladies. Slow down.  Let’s be honest.

It is soul-crushing to have a crappy date. It feels terrible to go out and feel as though you wasted your precious time. AND that’s if he is just a NO-GO. If he is a BIG ol’Loser, it’s worse.

And of course, you can check his social, but the #boldtruth: sometimes people post the very best or frankly the very stupid stuff, and he may just be better than that.

Using these questions as a way to eliminate, as best you can, possible dating candidates will:

  • Save you time.
  • Save your wasted energy by putting your hopes and dreams into the wrong person.
  • Teach you how to ask questions that are easy to weave into the conversation.
  • Allow you to READ between the lines.
  • Help you get to know him better.
  • Allow you to make a more informed decision about IF YOU EVEN want to go on a first date.
  • Encourage you to be powerful, to be strong, to take ownership of your experience.

When I was dating, I was tired of showing up and being let down.

My heart would hurt because I wanted so very, very much to find my life partner.

Even when I tried to remain upbeat about a date and say to myself it was “just for fun,” when it was a bust, it hurt.

So, I never wanted that to happen again and I developed these 5 must-ask questions BEFORE your first date.

Being a psychotherapist at the time, honestly, it was embarrassing for me to date guys I thought “should be” great…but weren’t.  I mean come on!  I was supposed to know about people and feelings and such.

So, I developed these questions with the psychology of people as the basis for them.

My last straw was this one guy.  He seemed great on paper (or rather on his online dating profile), but what he didn’t tell me was that he had ZERO FRIENDS.

Hey, if he doesn’t have friends, there is a problem.

So anyhow, I meet him downtown at a trendy pub, and he was there with his mouth full of braces.

He failed to email me about having dental reconstruction surgery about four days prior to our date.

I tried to go along with it…and started asking him about himself. “What did you do this summer?

It was gorgeous weather!”

I asked. His reply, “Nothing. Why bother.”

How could he have done nothing all summer? No hikes? No picnics? No swimming? No boating? No nothing?

Well, that was all I needed to walk out…that and the fact I was grossed out by his mouth.

I was 37 at the time.

There was another guy–I’ll call him The Tongue.

He had a bar in his tongue he neglected to tell me about.

Do you know what a bar is? It is about an inch long.

On either end, it has little balls so it doesn’t fall out.

It clanks against the teeth…chipping them.

It’s either a Fashion Statement or a Sexual Enhancement Device (yeesch). We went to dinner.

He took me to Chili’s.

Do you know what Chili’s is?  It’s a hamburger chain.

Now, I like a good burger, but this was not a place to go on a first date.

He ordered shrimp scampi.

Did you read above how I told you Chili’s is a hamburger joint? Not a seafood place?

After a quiet start, I asked him about his mother and family.

Does he have siblings?

“Yeah”, he said. He has an “idiot sister” who apparently “takes after Mom.”

I got up and left.

Leaving him to pick shrimp from his tongue bar. 

Those stories are the least painful. Some were fun though!

There was the guy who claimed he had a Ph.D. (By the way,  I have a Master’s degree, worked at Johns Hopkins at the time, had a private psychotherapy practice, owned my own home, etc. So, having someone who could keep up with my brains was important)….anyhow, guess what his Ph.D. is in:


Yeah, he actually said that, “my PhD is in LIFE”. *Sigh* and goodbye.

Then there was the Penguin Guy, the Living Room Pet Toilet Guy, the Nascar Guy, The Porno Freak Guy, Mr. Half-Calf, Mr. Can You Drive Guy, the I Love Football on Saturday and Sunday in the Fall and Golf on Saturday and Sunday in the Spring and Summer Guy….

My friends at work would wait with bated breath every Monday morning.

They couldn’t wait to hear my latest dating saga.

But, I became disillusioned. I became downright sad. I knew my Mr. SoulMate had to be out there and I was tired of just saying YES to any guy who liked my profile and asked me out. These questions are intended to be answered BEFORE you even GO on a FIRST DATE. Take it from me — someone who found their hunky hubby online.  I decided to create a system to weed through the, well how should I say it delicately, the losers!

So whether you have been trying to find your guy on Match or eHarmony or at the bar, you need to get a better understanding of who he is!! BUT, even before you get to the point of being able to ask him these 5 questions, you need to do a couple of things first.

First, Know Thyself

Look, I’m gonna give it to you straight because I don’t want to waste your time. If you think “ALL MEN ARE A**HOLES”…that is who you will attract. If you are afraid to speak up, that is a problem.

If you don’t have your own self together…you need to work on this FIRST. You deserve to attract into your life someone awesome, but you need to be awesome yourself.  You need to embrace your power as a woman.

To be completely open, I spent almost 2 years really doing work on myself before I met John. I had to examine why my previous relationships failed.

The only constant with my four failed major relationships was ME. Dang, it too! Because I really wanted it to all be their fault.

I asked myself, “Why do I seem to attract the same type of man?” What were my expectations? Were they too low? Too high? I had to really self-examine. And, I had to put up some boundaries around what was acceptable in my life and what wasn’t. And that was hard to do because I had never done it before.

For example, I said NO to working too much. I quit drinking. I didn’t allow my mom to influence me so much. I started exercising, eating better, and doing activities I enjoyed….with or without a guy. I got prepared. Because I KNEW my SoulMate was out there. And you know what? Your Soul Mate is out there, too. Maybe even in this very moment while you are reading this, he is thinking about you dear reader!

Second, Create a SoulMate Checklist

Do you really know what you want in a partner? In a lover? If you haven’t invested the time and mental energy in figuring out what you will and will not settle for, here is the How To Create a SoulMate Checklist. Because the truth is this, if you want a BIG, BOLD LIFE & BIZ you need to take personal responsibility (and, here’s some help with that too).

Decide if he is Worthy of Going on a First Date with You.  You have to do some basic research on this guy before you even have a date.  Let’s play out two scenarios that will cover most of the ways people meet each other these days.

The Online Scenario. If you found him online, you have obviously checked out his profile. You have ruled out the basics: he is not in a relationship, he says he has a job, etc. Now, I know they can lie, but it’s a start. You know his name and have looked at all his social media posts. Is he on LinkedIn? What types of pictures does he have on Facebook? Do his various social site profiles match his current posts on social media? What is he doing in these pictures?

Google him. Check all the social.

After you investigate a little, have one or two emails back and forth. Only ONE or TWO — don’t waste time.

How does he write? How much is asking about you vs. talking about himself? Is he upbeat? Trust your gut. Do not reveal too much about yourself. You want to be the one inquiring. You do not want to share all your secrets, dreams, and wishes with this perfect stranger and potentially give him more information than he needs.  Less is best for you to share.

Now, get on the phone. First, before you even get the questions, can you stand his voice? Once, this really nice guy and I had a great conversation, but there was no way I was going to bother going on a date. I frankly couldn’t stand his voice. Imagine living with someone for a lifetime whose voice you hate. Be discerning or picky if you must, there is someone right for you!  Next, start weaving in the questions! Go ahead.  Now is the time to be CURIOUS about him. Don’t get too in-depth or personal, but ask those five questions.

The Meet In-person Scenario. If you met him live and in person — at a bar, a museum, a work thing, where ever you have met him in person. You have the opportunity to ask him these questions NOW.  Don’t freak out. When you ask these question correctly, it flows.

Whether Online or In-person, these are questions you could ask anyone you may want to be in a relationship with! Point is, they reveal a lot, and they are completely socially appropriate.

The 5 MUST ASK questions BEFORE your first date!

Now I know when you scan these questions you are going to wonder, “Mary, I am going to sound like a fool if I just ask these straight out.” I have you covered.  I’ll share how to weave these questions into the conversation, but first let’s bottom line what they are!

  1. This question is an easy starter… What are your hobbies?
  2. Now for one, this could be sticky… What do you think of your mom?
  3. He may or may not be open to this… What are your addictions?
  4. Maybe lead with this one… Do you have a pet?
  5. And, finally… Do you have any friends?

I know you are thinking, seems a little pushy, right? Okay, so you are not going to ask the questions word-for-word exactly like that.  However, you DO want these answers.

Remember, you are asking these questions before the first date because you:

  • Deserve to know
  • Don’t want to waste time
  • Will feel even more excited when you go on your first date if his answers align with your relationship wants and needs

Trust me. Let’s examine the possible reasons why these questions can truly clue you into who you may be dating.

1. What are your hobbies?

If he has NO hobbies, you will be his only hobby and he will drain you. Therefore, if his hobbies are not in line with what you want in your life, you have to decide if it is a yellow light or a red flag. Remember your SoulMate Checklist?  Maybe you have “likes cooking on Sunday night” as one of your wants.  Well, what if he watches ESPN every Sunday with the guys and isn’t willing to change this? While he may seem nice, if he has NO hobbies or outside interests what does he bring to the table?

Don’t you want someone who is able to go has fun with and fill his LOVE TANK a little by himself? (here’s more about what a LOVE TANK is)

Ways to ask this question: “Bob, what are some of the things you like to do for fun?” or “What did you do last weekend?” or “What is something you enjoy so much that you lose all track of time?”

How do his answers fit in with your future life vision? Remember: You are worthy.  There are other men you can date.

2. What do you think of your mom? Has he made peace with the fact that we are all human? That we make mistakes? Maybe he loves his mom and has nothing but wonderful things to say about her? Maybe he spends every single Wednesday night with her at HER house because she cooks his dinner and does his laundry? Maybe he calls her a B****?

Psychological studies show a correlation between the relationship of a son and his mother to the relationship of a man and his lover. Men who have a positive relationship with their mothers are less likely to be hyper-masculine and deviant in their behavior.

Ways to ask this question: “Do your parents live around here?” or “What is a holiday tradition you do with your family?” or “Are you and your mom close?”

How do these answers fit in with the future vision of your life?

3. What are your addictions? Porn, drugs, football, work-a-holic, alcoholic, gambling, health fanatic, saves his belly button lint? This one is sticky. People with addictions don’t like to share them if you ask them outright. Maybe you will get a clue from his answer to questions 1 and 5?

It is important to try to get this one answered. AND it is important for you, as a woman, not to MINIMIZE what he says. Sometimes we don’t really want to hear what is being said because maybe you think it is not a big deal OR you can “help” him with it. Remember this: Actions speak more loudly than words.

Your actions Speak so Loudly I can't Hear a Word You are SayingClick To Tweet

Ways to ask this question: “What do you think people would say you spend too much time doing?” Now he may actually tell you the truth here. He may come right out and start sharing…too much in fact. OR, he may appear secretive. Some of this you will not find out for a while, so be vigilant, be curious, and be aware.  His lack of answering may be just as informative as a full response.

4. Do you have a pet? Seems simple enough, right? Does he travel such that having a pet just is not feasible? Have allergies? Hates animals? Is commitment-phobic? Maybe he wants to live on a farm and raise cattle? People usually come right out about their feelings about pets. Ladybug is my 16-year-old cat. I had her before I met John. If he said I had to ditch her….well, you know the answer. That would not have started things off well.

Ways to ask this question: “So do you have any pets?”  Ha! this is the simplest.

5. Do you have any friends? If he has NO friends, you will be his only friend and he will drain you! Now, granted some people are more loner types or introverts. Some men don’t have a lot of close friends. Others have a big posse they go out with every Friday night. I can hear your thoughts right now, “I want him to be my best friend.”

Great, I completely agree! However, if he doesn’t have any friends, it tells you several things. He does not know HOW TO develop and maintain relationships and there IS a reason why NO ONE wants to be around him. You may not have discovered it yet, but it is there.  This is a very important question; listen closely to his answer.

Ways to ask this question: “What do you like to with friends?” or “Tell me about the friend you have had the longest.” or “What do you think of having friends of the opposite sex?”

Here is an example of a full-blown conversation. 

Hi Tony, how was your weekend, what do you and your friends do for fun? Note: this covers friends and hobbies. He will answer.

LISTEN and try to HEAR the answer! Depending on his answer, dig a little deeper.

You could tell him about your weekend, maybe you walked your dog? Do you have any pets? Note: this covers the pets’ question.

Did you grow up here in (name of City)? Does your family live close by? Do you get to see them very often? Note: this covers the family/mom question, or at least sets up the conversation to ask about his mom.

So, if Tony says, “I was sitting around watching Nascar and eating Cheetos all by myself.”

You have a decision to make.  And, note: this would indicate addictions.

The whole point of this is to have fun while simultaneously getting down to some serious future life business.

Find out some key ingredients that make him up! Especially relevant is for you to honor your wishes for what you want for your own future.

Ask yourself, “How does this fit in with my future vision of my life?”

Remember, there are many men out there. Your Soul Mate is waiting for you.

Rule out the loser dudes by asking those 5 must-ask questions before your first date!

Here are some other goodies for you to devour as you develop a relationship with yourself and search for Mr. SoulMate:

I believe in you more than you will ever know! You deserve to have a BIG, BOLD LIFE & BIZ…and the SoulMate of your dreams! Here’s to you and your amazing relationship.


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