Single parents don’t have a lot of free time for dating. So when you get back out there, you tend to want to date as efficiently as possible while still enjoying yourself.
One way to do that is to avoid spending a lot of time on dates with people who aren’t a good match. Unfortunately, too many of us end up doing just that because we don’t figure out someone isn’t a good match until we’re several dates in.
But that’s because we don’t ask the right questions early on. We know some of the right questions, like whether they have kids or if they’ve been married before. But there are other questions that don’t immediately come to mind, yet they can offer some deep insight into whether someone is a good fit for us.
Think about asking these questions on or before your next first date. You might be amazed at how many second dates you skip as a result.
Why are you dating?
There are plenty of reasons for dating, from fun to sex to finding a lifelong mate. And while there’s technically no wrong reason to date, there is a right reason that makes you a match. If one of you is dating to find a lifelong mate while the other is looking for their next one night stand, even the first date might turn out to be a waste of both your time.
So ask the other person why they’re dating. Or if you feel that sounds odd or confrontational, try asking what their dating goal is.
What if they don’t know? That doesn’t have to be a deal breaker, but it might be a good idea to keep your other options open and not invest too much time into dating them until they figure it out.
What’s the most important thing in a relationship to you?
Just like dating, we all get into relationships for a variety of reasons. If you’re both on the same page in terms of looking for a relationship, the next step is understanding their priorities in a relationship.
If they think sex is the most important thing and you could happily go without sex, it might not be a good fit. On the other hand, if you both agree that sharing an interest in video games or gourmet cooking is important, you might be on the path to love.
Once again, some people might not be entirely certain about their answer. If they say they don’t know, try asking them to just give you the first thing that comes to mind when they think of the question. They might ultimately have a different answer, but that first answer might give you some insight.
What is one quality someone needs to be a match with you?
We all have some standard answers for what we look for in a partner: honesty, sense of humor, intelligence, etc. But this question is meant to go a little deeper than the standard answers. This is meant to go to the heart of what they, specifically, are looking for as opposed to what everyone is seeking.
For example, I know that to be a match with me, I need a man to be comfortable identifying and expressing his emotions. I just can’t connect with someone who is super logical and unemotional (not that being logical and unemotional doesn’t have its place, of course!).
By finding out the one quality they feel is a must-have, you can then identify whether or not you have that quality. If you don’t, you then get to decide if you want to invest in developing that quality or just walk away.
What three words would you use to describe relationships?
I love asking my coaching clients this question. The three words people use to describe relationships (in general, not just their own) can give you some serious insight into how they view relationships and what you could expect from dating them.
Their choice of negative or positive words will help you see if they view relationships as good or bad, despite whatever other things they might tell you.
And if they use a mix of negative and positive words? Maybe they’re conflicted. Maybe they know relationships are complicated and confusing. But because you ask for three words, you can also look at whether they use two negative and one positive or two positive and one negative.
Whatever they say, you’ll learn a lot from this one question.
What’s your favorite part of a relationship?
You might think this is the same as the most important thing in a relationship, but it’s not. At least, it’s not always the same thing. And like the other questions, it’s one that can give you some deep insight into how someone views relationships.
There are a few different ways they can answer. They might describe a feeling of connection that develops after being together a long time, for example. Or they might talk about holding hands or other ways of showing affection. Or they might say their favorite part is the early stages of the relationship, when you’re getting to know each other and everything feels new and exciting.
Whatever their answer is, it will help you get a better understanding of how they see relationships and whether your views are similar enough for a healthy relationship to develop.
Where do you see yourself in 3–5 years?
This might sound like a question more suited to a job interview than a first date, but it can be a great first date question too. Their answer can tell you a lot about what they want and where their focus is.
For example, if their answer revolves around going to school or getting a career advancement, you might learn that they’re a workaholic who would put work ahead of your relationship. Or if they talk about being married and having (more) children, you might learn that they’re serious about dating or that they’re looking for any warm body to fill an open position in their life.
The ideal answer would be one that’s well-rounded and describes multiple aspects of their life. If you find someone who gives you that kind of answer and their other answers are a good match for you as well, they’re definitely worth spending more time with.
These questions aren’t a guarantee that you’ll weed out all the people who aren’t a good fit for you on the first date. And they certainly aren’t a guarantee that you’ll find love on the first date.
But they are a way to get some important information without wasting a lot of time. And when you get one or more answers that are clearly not a match with what you’re looking for, these questions allow you to confidently skip a second date without wondering if you’d regret it later. You can walk away, or offer nothing but friendship, and be sure that it’s the right move.
Wendy Miller is a Post-Divorce Coach & writer. After years of settling for abusive and otherwise toxic relationships, she got fed up. Using meditation and other tools, she got to work on healing herself, setting boundaries, and only engaging in relationships (romantic and otherwise) that bring her joy. She wants to help other single parents find the love & happiness they seek, including and going beyond romantic love. She lives in Florida with her two sons, where she homeschools while solo parenting, while surrounded by what feels like a zooful of animals.
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