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The difficulties of dating go without saying. We live in a generation where women are expected to abide by innumerable unwritten dating rules, including what and what not to ask on the first few dates. So we deprive ourselves of precious time talking about things that don’t even matter. Well, I want a soft life, and closed mouths don’t get fed.


“What’s not said is not understood” is one of my favorite coined mottos. Manifesting my best soft girl life doesn’t include biting my tongue from asking necessary questions and sticking to ego-stroking facts of what a great school he went to or how cute that his first son must share his first name. It includes having a partner who’s ready and willing to not only match my energy but also contribute to my lifestyle. So tell me, how I’m supposed to do that if we’re busy talking about how his favorite thing to do is go to Lakers games? (Like, honestly, who really cares?)

Now, I’m not saying start going into dates, guns blazing, asking about credit scores, and how many kids he wants. But that’s not to say you shouldn’t want to have an idea of his financial setup and goals. The key is subtlety. While I’m no dating expert and quite single, I’ve found myself wasting less time by wording questions in a deliberate way that helps sift through the Prince Charmings and Mr. Right Nows. These are a few I recommend:

“Tell me a red flag about yourself that you think I should know.”

You know how job interviewers ask you to describe your biggest weakness? This is the same idea. It’s an opportunity to show vulnerability and self-awareness. Follow up by asking if he’s actively working on improving. Whatever the response, it’s up to you to decide if it’s alarming enough to either run or stay. But I can’t emphasize this enough: PLEASE don’t take this as a charming challenge of “I can change him.” He’s (fill in the blank) years old. He’s had (fill in the blank) amount of years to change. If he hasn’t, he has no desire to.

Couple-laughing-in-the-grass-drinking-coffee-in-the-park

Angel Santana/ Getty Images

“Do you do your work for the money or because of passion?”

I like this question because it indicates how attached he is to his career. I’ve found men who do what they do because of passion are more willing to sacrifice quality time for work. Passion is admirable, yes, but you’re looking for a romantic partner – not a business consultant. You’ll get an idea of his work-life balance. Is he the type to take time off for a couple’s vacation? Or will you spend your summer Saturdays local because he can’t pull himself away? While the ones who work for money may have more free time, are contrarily miserable and up to start a new career path at some point. The new question is, are you willing to stand beside the financial stall that it might put him through?

“What do you want your ideal household with your partner to look like, responsibility-wise?”

If you want to know if he’s the type to take care of all the bills or expects you to go 50/50, ask this question. It’s worded perfectly for him to answer however he interprets. Whether it defines who pays the bills to who takes out the garbage. However, if he’s not sure how to answer, elaborate by saying, “Do you prefer your partner to have the more traditional role of only taking care of the house, or do you look forward to sharing all of the responsibilities down the middle?” He’ll most likely ask you in turn, and it’s up to you to be as honest about your expectations as you feel at that moment. I gently communicate my preferences even if they differ from his because I don’t want to create false expectations for myself, trying to gain his favor.

“How much of an influence does your family have on your love life?”

We love a family man. It’s the cornerstone of healthy relationships. But for some, there is such a thing as too much family. It’s important to know how close they are so you’ll get an idea of how much their opinions can affect the relationship. Consider the following: Will there be tension if you skip family events? How willing is he to create boundaries necessary for your comfort? Can you rely on him to put his foot down when his sisters are being overprotective?

Then, once we’re in a more comfortable place, I’ll even ask how his family handled the end of his last relationship. His answer can indicate how emotionally involved they were, so listen for hints of them missing her or having complete disdain. (How they talk about her is how they’ll talk about you.)

Soft Girl Dating

Prostock-Studio/ Getty Images

“When did you realize you were ready to settle down?”

This question can be scary to answer but only depending on his true intentions. It assumes that you’re both on the same page. Just the thought of a serious relationship will make the biggest serial dater squirm and accidentally admit that he’s not interested in anything serious after all. He may also pull the nonchalant card by reciting the “I’m just vibing” script. *gag* Whereas, a man of intention will straight up say exactly how he knows he’s prepared to enter a committed partnership. Don’t take this as 100% Bible, though. Continue to make sure his actions match his words because there’s nothing worse than being tricked into a situationship based on empty promises.

Really, all we can do is be intentional, learn lessons, and apply those lessons along the way. There’s no foolproof way of dating, so we can’t afford to waste time not asking the right questions. While knowing his zodiac sign is arguably quite important, let’s make sure we’re setting up our futures for everything we deserve and more.

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Feature image by Maskot/Getty Images

 

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