DATING PEOPLE WITH KIDS

4 Things To Know Before The First Date

Kenneth Smithee
5 min readApr 8, 2019

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If you’re like most people on the dating scene, you find it tedious and time-consuming. Whatever your age, stage, or circumstances, the search for someone with whom you find chemistry and are interested in spending time is a land riddled with mines of confusion and frustration. It’s even more complicated when children are in the picture.

Whether you find your prospects through dating apps, friends, or in public places, there are questions you can ask to reduce this frustration. The fewer unsatisfying first dates you go on, the better your rate of conversion will be for second dates and ultimately LTRs.

You probably know that before you meet, you should first be ok with the sound of their voice, whether they can put a sentence together, that their personality and location seem to line up with your preferences, as well as other basics such as keeping first dates short and inexpensive.

Everyone is looking for chemistry which often reveals itself naturally by way of intuition more so than thought. But it’s useful and wise to collect information about someone’s circumstances when they have children. Contrary to what many people say, it’s ok to judge. In fact, this is the exact right and best time to do so. You need to judge how they come across and their situation relative to you. Of course, you shouldn’t judge too quickly or without considering the bigger picture.

There are 4 deeper insights to know before you go on a first date that increase the chances of a second one.

These need-to-knows, in the form of questions, are for people seeking a relationship rather than a hook-up, and those willing to talk on the phone before meeting. The phone call is critical although you should ask these questions conversationally. Otherwise, you’ll come off like an interrogator rather than dating material. You can get answers to some of these questions by texting but I recommend hearing someone’s immediate response.

To be sure, no one is going to list everything you need to know in their dating profile. So, it’s incumbent on you to ask these and other questions to get a sense of the person with whom you’re getting involved. Their life situation is as relevant as who they are as a person.

Finally, the answers you get to these next level questions won’t be right or wrong. They simply help you uncover potential pros and cons relative to your situation and preferences before you even meet. You don’t have to get answers to all of them but the farther you have to travel for the first date, the more I’d try to collect all 4.

How old are your children and what are they like? Knowing how and what someone says about their kids can reveal both stability and relationship drama. If they have a troubled child, if all their children opted to stay with the other parent full time, if their kids are very young or they are out of the house, if they are doing well in school, if they talk about them hesitantly or with great pride— whatever information they offer you is useful in getting a feel for their situation. People in their 40s and older generally look for clarity and stability more than those in their 20s and 30s. When someone has kids or is over 40, their life is no longer a blank slate. So, you should at least assess what you’re potentially in for.

What’s your schedule like with your kids and work? This goes to availability and where you’ll spend your time. If someone has one or more children with them all or most of the time, they’ll likely need to come to you and be willing to do so. If that’s your situation, the reverse may be true. If they travel a lot or work in the opposite direction from your home and work, you may be looking at a weekends only thing. That’s not good or bad per se. It’s relationship intel that informs when and where your time would likely be spent.

What’s your kids’ relationship like with their mother (father)? This insight can reveal drama in both the near and long term. It speaks to stability and harmony that surround the person’s everyday life. The stress of a bad relationship with one parent often finds its way to the other. Also, people have good and bad relationships with their exes. So, unless it’s fraught with issues, it’s not itself an indication of anything. As with all of these questions, no single answer should determine whether or not to date someone. But taken together they can inform your thinking.

How long have you been single? It’s helpful to get perspective on whether someone is separated, divorced, broken up, or widowed, and for how long. For example, someone who’s been separated for 6 months with two kids is in a totally different place than someone who’s been divorced for 2 years with no children. This question helps assess someone’s emotional stability and clarity in what they’re looking for. I’d ask this one whether or not someone had children but kids certainly add another dimension.

Of course, you can still be misled, as with the common frustration that your date looks nothing like his or her photos. You can’t know anything 100% in dating or in life. There’s no foolproof way to tell if someone’s lying and most of us delay revealing the negative stuff. You just want to put the odds in your favor.

As for dating apps, they help you meet more wrong people faster. But that’s a good thing because dating is a numbers game; it usually takes time to find someone you’re attracted to and who’s interested in choosing you back.

If you’re dating someone with children, knowing these 4 things will help you make better choices relative to availability, drama, and stability. You can’t know everything at the outset; that’s not how relationships work. But you can get perspective and make more informed choices that help turn more first dates into second ones.

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Kenneth Smithee

If I can help just one person with their relationship, then I’m not doing my job well enough.