5 Things You Should Always Ask on a First Date

Ahh… the thrill of dating. Can we all just agree that it’s stressful? But, the truth is, a first date is the best time to sift the wheat from the chaff. To decide whether or not to move forward before we get too close. Getting to know one another under such pressure is hard. But, it’s much smarter and kinder to both of you, to discover as much as you can as early as possible.

You have little invested at this point. And while you’ll likely know early on whether or not there’s an attraction, you need to get the basics out of the way before you allow that to sweep you off of your feet. Don’t move forward with someone who’s not compatible, or worse yet, completely wrong for you—for both of your sakes. And while you need to be somewhat sensitive as to how you ask, get this info by the end of the first date. 

Tell me about your past relationships. (What kind of relationship can you expect?)

Face it, you want to know anyway. And while it may seem too forward on a first date, you need to look at this as an informational meeting. Not only is it good to know what’s happened in the recent past, you need to delve as much as you can into the far past. Listen to how they speak of their exes. Is it with respect? Do they present themselves as a victim in every single case? Also pay attention to how frequently they change up relationships. In the dating world, it obviously takes multiple dates with multiple people before you likely find a good match. But, if your date brags about how often they date as if they are setting goals on a conquest, look out. You might just be a number to them. 

Isn’t the server funny/weird/rude? (Find out how they treat people.)

I’m convinced you can learn more on a dinner date than any other kind. And while you may wish it were simply coffee if the date isn’t going well, there is a tremendous amount to be learned beyond the conversation you have among yourselves. Specifically pay attention to how your date handles others in the restaurant. Are they patient and polite with the hostess? If there’s a wait, do they handle it well? How do they treat the wait staff? Do they make fun, act condescending, or belittle them? Remember, most people are on their best behavior on their first dates. And while it’s obviously important to pay attention to how they are treating you, you will learn volumes more from how they treat others. 

Tell me about your life’s work/job/greatest passion. (Find out their views on money/time/giving.)

We spend a lot of time at work, so how we feel about it, how we handle it, and how we talk about it matters. This will become a frequent conversation in your life should you continue on in a relationship with this person. Find out how they feel about their job. Do they show gratitude or entitlement? Do they put a value on life outside of work, or do they work too much for your taste? Do they speak respectfully of their boss, or talk as if they know better? Of course, we all have stressful times in our careers, so if that’s the case, give them a break. But, overall, work attitude says a lot about how a person handles themselves in other areas of their lives as well. 

What are you looking for in a relationship? (Are you going to be available?)

Not everyone in the dating scene will be looking for the same things that you are in a relationship. While you may want something long-term, they may be looking for something very casual and uncommitted. There is no sense in getting too close to someone who doesn’t want the same kind of relationship. So ask them what they are looking for. But before you do, make sure you know what you are looking for as well. Otherwise, you may find yourself trying to brush off your own wants in order to fit this person into your life. Also keep in mind: the type of relationship they seek will tell you a lot about their availability. Some people want to date, but simply don’t have time for it in their lives. If you are also super busy and okay with a monthly date, fine. If not, it’ll become a thorn in the side of your dating life. 

What’s something I should know about you? (Find out exactly who they are.)

Maya Angelou has a quote that I reminded myself of before each and every date: “When people show you who they are, believe them.” Remember, people know themselves much better than you know them. In initial meetings they will give you hints—often in a joking way—about who they are at their core. If they make offhanded comments about being mean, or superficial… guess what? They are mean or superficial. So ask them to reveal something about themselves they may not have otherwise. Rule number one: People will tell you who they are. Believe them.

Utilize the first date to your (and honestly, your date’s) advantage. Ask questions and seek to find answers that will reveal the most about your chances of moving forward. It’s better for everyone involved to be honest and learn the most possible early on. If you’re not right for each other, two more weeks of dating won’t change that. Choose your dating opportunities wisely, and respond gently and respectfully to those you decide you won’t move forward with.

Laura Polk is a writer, speaker, and textile designer residing in North Carolina with her three children. Since becoming a single mom, her passion to minister to this group has led her to encourage successful single mom living through The Christian Single Mom on Facebook. Follow her journey through her blog or get a glimpse into her quirky thoughts and inspirations for design and writing on Pinterest.

Publication date: May 12, 2016

Photo credit: © Getty Images/clownbusiness