How do you know if the person you’re dating is a keeper? I get this question all the time from clients, conference goers – even from friends. And when Valentine’s Day comes around, many people are drawn to evaluate their relationship compatibility and happiness. There’s something about watching a sea of couples descend upon local restaurants, bars and bistros that makes you wonder, “Are they happy?” and then comes the inevitable, “Are we happy?”

In order to help couples evaluate their relationships more easily this Valentine’s season, I’ve come up with a list of questions that will not only provide food for thought, but might even initiate a communication breakthrough. It always amazes me how couples can go for weeks, months, even years without diving deep and connecting on core values, beliefs and goals. I’ve even counseled newlyweds who are shocked to discover they don’t agree on whether or not to have kids.

You don’t need to barrage your lover with all 50 questions at once, but scan the list for the ones that stand out to you. For example, maybe you already know how your partner likes to relax, but you’d love to know when they last had a good cry, or what they consider their most prize possession. This list is good for couples who have just started dating, or are in a relationship.

Explore together with these Valentine’s Day compatibility questions:

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