Columbia Pictures
Stephanie Hallett
December 09, 2016 4:38 pm

Anyone who’s looking to couple up wants to land in a healthy and fulfilling relationship. But it can be tough to determine if the person you’re seeing is genuinely kind and considerate (i.e. worthy of a second date) or totally not right for you. That’s why we put together this list of questions to ask on a first date if you want to avoid a relationship with a jerk; They’re simple enough to remember, will fill in any gaps in conversation, and should — in theory — help you to learn more about your prospective paramour.

Here’s one key thing to remember, though: When you get answers to these questions, really pay attention to what your date is saying and listen to your intuition. If their responses don’t jive with your values or ethical code, then they might not be the right match for you.

1How did your last relationship end?

Yes, it’s a first date. But if you’re looking for a serious relationship, pretty much any question is fair game. So asking about their last relationship is an important way to determine 1) if they’ve ever been serious with someone before and 2) if they can reflect critically and compassionately on the experience.

“His (or her) behavior here can be very telling, [especially] if he trashes his ex (or women in general),” says Natasha Burton, co-author of The Little Black Book of Big Red Flags. She adds that taking zero accountability for what went wrong in his last relationship is probably a bad sign but, “alternatively, if he chalks up his single status to mere chance or his own mistakes, he’s probably not a jerk.”

2Why are you single?

This is a good follow-along question to “How did your last relationship end?” because it gives your date a chance to explain why they’ve remained single up until this point. Their answer will also reveal whether or not they have space for you in their life — i.e. are they looking for a hook-up only, are they “focusing on their career” (which is fine, but might not leave much room for a relationship), or if they generally seem bitter about dating. Remember to really hear your date and check in with yourself about how their answer makes you feel.

3How do you like being a [insert job title here]?

This question will help you learn more about how your date relates to other people. Are they a collaborator? Good quality to have in a partner. Are they wary of everyone he works with? Seems like they have trust issues. Adds Burton, “A [person] who answers this question by talking primarily about how much money [they make] and how [they get] to boss other people around is more or less a total jerk.”

4Who did you vote for?

This question might make you cringe, but if the 2016 election has proven anything it’s that a difference of political opinion can tear otherwise happy couples apart.

5So tell me about yourself.

Seems simple enough, right? But this introductory question can reveal a lot about your potential partner. “If your date can tell you something interesting about his/her personal life and be transparent, honest, and open about who he/she is, maybe share a funny story about his/her childhood, then he/she might be a keeper,” certified sex therapist Dr. Tammy Nelson, author of The New Monogamy points out. “If he/she answers with a stone faced, ‘Huh?’ and drools out of the corner of his/her mouth, it might be a sign that conversation is not his/her strong suit.”

6 Do you want to get married? Do you want kids?

While some dating guides might urge you to steer clear of these so-called “heavy” questions on a first date, we say go for it — there’s nothing to be afraid of. Burton puts it decisively: “If someone is going to take offense or think you’re coming on too strong by just trying to get a sense of their life goals, he or she is not the person for you. We should be able to have grown-up conversations about what we want out of life.”

Mic drop!

7Here’s a question to ask yourself after the first date: How did being with your date make you feel?

This question is all about checking in with your intuition. Is your gut telling you there were red flags to watch out for? Or did something just not seem quite right about your chemistry? Pay attention to that.

Says Burton, “Close your eyes if you have to and just give yourself five minutes to check in with your emotions. Could you be yourself? Or did you find yourself censoring your beliefs or opinions?”

8 One last question to ask yourself: Did I get to talk, and did I give my date space to be themselves?

Being in a relationship is a give and take, and most people these days want things to be pretty much 50-50. So if one of you took up way more space on the date, that could be a sign that you’re not right for each other.

“Make sure neither one of you dominates the conversation to fill in long, dead, empty spaces,” says Nelson. “There shouldn’t be any awkward spaces in the conversation. If it flows, get [their] number. If it dives, lose [them] and go home and curl up with Netflix. Don’t waste a night off when you could be spending it with someone you enjoy being with — you!”

Amen to that!

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