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4 Questions You Should Always Ask on the First Date

You probably know what’s not appropriate to ask on the first date. On the other hand, knowing the things you should bring up during your conversation is really important.


Psychologist and CEO of LoveIn90Days.com, Diana Kirschner explains that these questions can help you learn whether the person you’re on a date with is the right match for you. The questions have the power to transform polite chit-chat into an amazing discussion that can show you the heart of the person you’re on a date with.

“Most of us just skim the surface with a new person. As a result, you can come across as fake and empty. The more real you both are, the more connected you’ll become. So instead of ending the evening feeling like semi-strangers, you’ll have the sense that you actually get each other,” says Kirschner.

Here are the 4 questions you should ask on the first date:
1. What in your life would you say you feel most grateful for?

“This question can tell you a lot about his value system and whether it’s in sync with yours,” says Kirschner.

For example: The person who says that he’s thankful for having amazing friends who are always there for him is totally different from the person who says he’s most grateful for the big promotion.

2. Do you like adventure?

This question will help you reveal if your date is a marriage material and will give you a chance to talk about the crazy, adventurous experiences you’ve had.

“A planner and a thrill-seeker will generally have a hard time making it work. Ideally, you want a partner with a similar level of adventurousness,” says Kirschner.

If you’re a of person that wants to plan for a trip ages in advance, and he’s the type to head on a last-minute getaway, you might not click the same as with someone who has your taste of adventure.

3. What in your life would you say you feel most grateful for?

This question will help you get inside your date’s past without leaving an impression that you’re nosy.

“Learning about how he grew up will clue you into his earliest template for love relationships. If a person is from a difficult background, that often indicates there is trouble coming down the pike. We’re not saying it’s an automatic deal-breaker if his family life was less than ideal, but consider it a warning that you may have to deal with some issues in the future,”says Kirschner.

4. If you could have anything you wanted, what would your dream life look like?

This is the perfect question to learn whether your future visions are compatible. Is his career-driven or free spirit? Is he a forever bachelor or family-oriented guy? These are all key things to know about the man you’re dating.