The 5 Most Important Things To Know About Someone Before You Start Dating Them

Don’t be scared to ask the tough questions …

Most of us go into first dates hoping for the best, which means hoping this person will be “the one” we fall deeply in love with and who will end our lonely single days forever.

With that hope comes an eagerness that’s may be tempered by reluctance to pose some of the most important questions to ask someone when you’re getting to know them.

The reason we don’t ask these questions is because we often don’t want to know the answers, but it’s important to know a few basic facts about someone before you commit to spending more time dating and possibly developing a relationship.

Without knowing the facts, you could miss some serious red flags and waste a huge amount of time in your search to find true love. And we don’t want that.

Here are the five most important questions to ask on (or even before) first dates when getting to know someone new.

1. Are you married or in a relationship?

Seriously, you say, you need to ask that question? My 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 cheat and find someone they can fool around with. 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 or otherwise committed person. Being involved with someone who is married or in a long-term relationship brings with it a multitude of issues, most notably making it very difficult for you to find your one and only, no matter what they say to try convincing you otherwise.

And that is the goal, right — finding the one? If so, you may want to move on.

If the answer is no, you can go to the next question.

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 you not date someone who has been divorced within the last two years. Divorce wreaks havoc that regular break ups do not and the recovery period may be 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 breakup 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 solid period of time, not just because they’ll have had time to recover from the breakup itself, but because it’s more likely that they’ll no longer feel attached to the person they broke up with.

Nobody wants to date someone who is still holding a torch for someone else.

3. Are you employed?

One of the first questions many people ask when they meet someone new 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 many people do a variety of things at once.

A more important question to ask when getting to know someone is, “Are you currently working?”

You want to know if they are financially and emotionally secure. No one wants to get involved with someone who can’t carry their own weight financially. And 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 healthy relationships.

And don’t think that you can fix them because you can’t.

4. Do you get along with your family?

Family forms our fundamental relationships, so how it’s important to know how someone interacts with their family if you’re thinking about dating them.

If your date talks about the close relationship they have with their siblings and says their mother drives them nuts but they talk 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 they haven’t seen in years, then it’s possible deep emotional connections might be more difficult for them.

The basic human connections we make as children influence who we are as grown-ups.

Someone who has a rough relationship with their 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 this, or maybe you are willing to make their kids your priority as well.

But maybe it’s not okay with you. Maybe you want to always be first, or maybe you aren’t ready to have kids. And that’s okay, too.

But ask the question, because kids always will, and always should, come first, no matter what you might tell yourself going in.

Dating is time-consuming and emotionally fraught under the best circumstances.

You don’t want to waste even one minute on someone who raises red flags. Red flags should be noted and acted on.

Ask these questions and get your answers early so you can decide whether you want to fish or cut bait right away.

There are other fish in the sea, fish who might be better for you — and tastier.


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3 thoughts on “The 5 Most Important Things To Know About Someone Before You Start Dating Them”

  1. I dread that last question. 3 kids puts a look on guys eyes I don’t ever want to relive. It’s why I’m officially not dating. In fact maybe that’s what I’ll specifically do….. put a tinder post up for a friend’s with benefits situation. One or two days a week. Some textinh. Mostly sex, conversation and some cuddles. A date here and there. Nothing that will lead to marriage. Just someone I like and can get along with and have fun with in and out of the sack without any need for it to go anywhere.

    But…..does that exist? I don’t know that it could. But if you make it exist I suppose it can be done.


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