Questions to ask a person you are dating


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We all have values that direct us and help us make decisions — problem is most of us have never articulated what those values are. Not all values are the same and sometimes you can have two very good people with very good values, but those values can feel at war with each other.

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Both values are good, but if not articulated and discussed it could be a point of high conflict if the responsible person likes consistency and persistence, while the risk-taker likes changing things up and going for the impossible. Take me for example, one of my core values is authenticity. I struggle being in a job, friendship, situations, etc. Thus my career path has been anything but straight-forward, which could drive any sane person crazy. Thankfully, my wife has been very supportive because she knew this was the way I was wired from the beginning and it aligns with her core beliefs, as she enjoys change and pursuing things off the beaten path.

Are you fitting and conforming to some abstract idea of what you think they want? Or are you blossoming and flourishing into who you really are? Is your partner trying to force you to become like some figment of their unrealistic dating imagination? Or are they challenging you to become a better, authentic you? Not trying to change you, but trying to bring the best to the top. However, for many of us our fallback communication plan will be the one our parents laid out for us.

Holidays, especially, are giving you a glimpse into how your partner has been taught and trained.

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Your partner can look and smell like a rose, and yet continue to prick you with their sharpened barbs. Does your partner seek out ways to understand how you receive love and meet that need? Do you do the same? When someone loves from their strengths they know who they are and are drawing from a deep, full well to give to you without demanding a drink in return. Honestly, going into marriage with my wife I really struggled talking about money.

I let money and the honest conversations about it become a wedge in my relationship. Conversations about money can be the great time bomb in a relationship. When you think about your future together, can you list three things that you think would be excruciating to let go? Identify what you feel are non-negotiables now so you can avoid any large, gaping ravines ahead.

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Does religious faith play a role in your present and do you want faith to play a role in your future? What do you truly believe about how to live your life and what happens when you die? Weighty questions, I know, but important ones. I really believe that if there are large differences in your faith now, those will only become bigger and more cumbersome as your relationship progresses. Especially when kids come into the equation. How will you raise them?


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Please know that we still offer the option to. You will find an "opt-out" button at the bottom of the page, in the footer. You will then be presented with the same consent screen next time you access the website if you opt-out. When things are super new with someone, it's easy to mistake puppy love for the real thing. But not if it's real.

If you like to wake up at 6AM to go on a early morning jog, and the person says they like to get up at 1PM for a good greasy brunch, you might have to compromise too much to make it last. If he has a strong bromance going on, maybe there's no room in his life right now.

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Super embarrassing to ask, but it's super important if you are at a stage where you're looking to get more serious and start a family. If it's a cottage in the woods and you dream of a penthouse downtown, it might not work out long term.

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It's really not cool to have to be afraid to express yourself because they are.