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6 Passive, but Telling First Date Questions

Updated: Feb 9, 2021

It’s the first date which means both of you made it past what may have been a grueling screening process. Congrats, but now it’s time to get down to “serious business”. It’s not enough to just make it on the date. You must have some level of chemistry or gift of gab to get to the next level. While some people are quiet and awkward on the first date, others can be downright chatty (in all the wrong ways). I’ve compiled a list of 6 very telling questions to ask when you’re trying to determine if you’ll be using the potential second date outfit you have tucked in your closet.

1. What’s your favorite holiday?

This will give you a chance to see what he values without you prying him with questions about his religion and/or finances. Pay attention to the “whys” he gives in his answer. If he doesn’t volunteer them, ask follow-up questions based on his answer. This is bound to be fun and can definitely steer the conversation for a bit.

2. Ask opinion questions to get a feel for if he’s opinionated or not

Lean into it and ask something like, “What’s the better date: a church picnic or a family dinner?” The object is to spark a conversation with your options. Of course, no one wants to go on a date at either, but choosing between two tough decisions is a perfect display of his thought process. Relationships work better when you love the way your partner thinks. If a man’s thought process turns you off immediately, it’s a bad sign for the relationship. Check out how he arrives at his answer on this one for clues to his critical thinking skills.

3. Where have you always wanted to vacation?

This will give you a sense of his desire for adventure. If you’re looking for a travel partner or someone who’s down for a good adventure, this question can shed some light on if you’re compatible or not. If he says something low maintenance or local, he just may not be an adventurous person. If you’re not adventurous, this may indicate you may be a good match.

4. What’s your favorite game?

Not only are games fun conversation starters, but they tap into a person’s personality in a different way. His answer will tell you his level of competitiveness or at least clue you in on it. Competition can be good/fun in relationships. If you’re not the competitive type, this answer will help you figure out if their competition level is something you can hack.

5. Who’s your favorite family member?

While the backstory can be fun, it can also give you an opportunity to possibly understand his family structure a little better. If he tries to only answer the question with the name of the family member, inquire about why this person is his favorite to get backstory. Listening to a man talk about his family in any capacity can be very insightful.

6. What would you do if you won the lottery right now?

This is a basic money management question… but a fun one. You can gather important information about how he prioritizes his money. What’s the first thing he would do? Will he pay off his debts? These are things that speak to his financial mentality and guess what?... that’s important to YOU if you’re dating him.

Have fun, but definitely make assessments from his answers. Am I saying jump to conclusions? Absolutely not. This should be fun and informative for a first date, but it should tell you a little more than you would have known. Also, make sure you can honestly answer all of the questions that you ask him. There’s a high likelihood of him flipping the question back to you after he answers.

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