Are you wondering what questions you must ask someone on a first date?

We all go into our first dates hoping for the best. Hoping that this will be the ONE who will end our lonely days forever. And with that hope comes a reluctance to ask questions.

Why? Because we often don ‘ t want to know the answers.

It ‘ s important to know a few basic facts about someone before you commit to spending more time developing a relationship. Without knowing the facts, you could miss some serious red flags and waste a HUGE amount of time in your search for the ONE.

And we don ‘ t want that. So ask away…

Here are the 5 Most Important Questions To Ask On A First Date:

#1 – Are you married?

Seriously? Do you need to ask that question? The answer is a resounding YES!

You would be amazed at how many married people out there want to date other people. Some of them are in open marriages, and some of them just want to fool around. Either way, you want to know the answer.

If the answer is yes, you need to decide if you want to be involved with a married person. Being involved with a married person brings with it a multitude of issues, most notably making it very difficult for you to find the ONE, no matter what he tells you.

And that is the goal right? Finding the ONE?

#2 – How long have you been single?

Once you know they are single it ‘ s important to know how long they have been single.

As a general rule of thumb, we experts recommend that you not date someone who has been divorced within the last two years. Divorce wreaks havoc that regular breakups do not, and the recovery period is longer. A newly divorced person just won ‘ t be ready for you, in spite of what they might think.

If your potential partner has just gone through a non-marriage break up, that could also be a red flag. Someone who is newly out of a relationship could be, consciously or unconsciously, looking for a rebound relationship. You do NOT want to be the rebound person.

Ideally, your prospective mate would be someone who has been single for a period of time, not just because they have had time to recover from a breakup but because it ‘ s more likely that they are no longer attached to the person they broke up with.

Nobody wants to date someone who is still holding a torch for someone else, do they?

#3 – Are you employed?

One of the first questions we ask when we meet anyone is ‘ What do you do? ‘ It ‘ s what Americans do. And it can be a tough question to answer, especially in this day and age when people do a variety of things at once.

A more important question is ‘ Are you currently working? ‘

The reasons you want to know the answer to this question? Because you want to know if they are financially and emotionally secure.

Financial security is obvious. No one wants to get involved with someone who can ‘ t carry his or her weight financially. Emotional security is a tougher one.

People who are unemployed are often in a delicate position emotionally. They could be actively seeking work and unable to find any. They could be thinking that the work out there is below them and refuse to compromise. They could have had issues at an old job that continue on into new jobs. All of these situations could lead to insecurity and low self-esteem.

Insecurity and low self-esteem are not things that lend themselves well to a healthy relationship. And DON ‘ T think that you can fix them because you can ‘ t.

So ask not only ‘ What do you do ‘ but ‘ Where do you do it? ‘

Want to talk first dates? Me too! Let’s do it….

#4 – Do you get along with your family?

Really? Knowing how someone gets along with his or her family is important.

The family is the fundamental relationship of someone ‘ s life and how they interact with that family is important to know.

If your date talks about the close relationship he has with his siblings and that his mother drives him nuts but that he talks to her every Sunday then you know that this person is capable of a healthy emotional connection.

If your date talks about the family that lives across the country who he hasn ‘ t seen in years, then it is possible the deep emotional connection might be more difficult for him. Why? Because the basic human connection that we make as children influence who we are as grown-ups. And someone who has a rough relationship with his family could be tough to truly connect with.

So ask the question and listen carefully to the answer.

#5 – Do you have kids?

This one is SO important because kids change everything.

Kids can, more than any other single thing, affect a relationship because kids are, more often than not, THE priority. They will be made the priority above you every single time. Every single time.

And maybe that ‘ s okay with you. Maybe you have kids, too and understand the priorities. Or maybe you are willing to make his kids your priority as well.

But maybe it ‘ s not. Maybe you want to always be first or maybe you just aren ‘ t ready to have kids. And that ‘ s okay.

So ask the question. Because kids will always come first, no matter what you might tell yourself going in.

Dating is time-consuming and emotionally fraught, and really you don ‘ t want to waste even one minute on someone who raises any red flags at all. Red flags should be noted and acted on.

So ask the questions. Get your answers early. Get your answers so you can decide to fish or cut bait right away because there are other fish in the sea. Fish who might be better for you. And tastier.

Going on a first date and feeling nervous?
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Email me at [email protected], and let’s get started!

Mitzi Bockmann

I am a NYC based Certified Life Coach and mental health advocate. My writing has been published on The Huffington Post, Prevention,  Psych Central, Pop Sugar, MSN and The Good Man Project, among others. I work with all kinds of people to help them go from depressed and overwhelmed to confident and happy in their relationships and in their world.