Learning relevant details about a guy you don’t really know is a tricky balancing act. If you want to seem casual while still learning everything you want to know about him, here are a few questions to get you started.
“What’s you favorite sports team?” Knowing whether or not the person you’re considering dating is addicted to Fantasy Football or hates every organized sport ever created will give you a good indication of how they spend their free time and what their values are. Is he the obsessive, tribal kind of person who lives and dies by his identity as the fan of a certain team or is he a well-adjusted person who only dabbles in sports fandom? If you’re one of these types yourself, this question will also tell you how compatible the two of you are.
“Politics are crazy these days, huh?” Now, at this point in history, most sane people would do just about anything to avoid talking about politics, but if the political views of your dinner partner are make-or-break for you, it’s important that you know where they stand. If you’re very lucky, he’ll say something like, “Honestly, I’m so sick of politics right now. Can we talk about something more constructive?” If he says that, you can go ahead and propose.
“Where was your last vacation?” Where a person chooses to go on vacation will give you a good idea of how compatible you are. For instance, if you’re a die-hard city person and you find out that the guy you’re on a date with loves nothing more than a trip into the Australian Outback for a week or into the Amazon, you might have very different ideas of what happiness is.
“Who’s your favorite actor?” If he responds with something like, “Scarlett Johansson because she’s hot,” you have everyone’s permission to get up and leave because clearly, he’s a jerk. If he says “Mark Wahlberg because Transformers is the greatest film franchise of all time,” you’ll learn certain things about his level of artistic sophistication. The kinds of movies and television a person likes can tell you an enormous amount about their tastes in art, which might be a deal breaker or an instant selling point.
“What was the best part of your day?” This simple question will give you a good idea of his values. I once had a guy tell me that the best part of his day was high-fiving a little kid he rode his bike past on his way to work. Adorable, right? That pretty much sealed the deal for me—in fact, we’re still together.
What was high school like for you? You may be noticing that some of these questions are pretty vague, but the vaguer the question, the more revealing his answers because the way he chooses to interpret what you ask will tell you everything. High school is a low point for most people, but if he says he was the captain of the football team and dated all the cheerleaders or a computer geek who stayed inside all day playing video games by himself, you’ll know exactly what kind of guy you’re contending with.
Have you ever spent way too much money on something you wish you hadn’t? If he says no, you’ll know he’s lying. If he answers the question truthfully, you’ll either discover he’s a pretty good guy who’s responsible with his finances or someone who’s prone to ill-advised impulses. You should probably answer this one too, just so he has something to go off of.
Do you like your job? Is the guy you’re with ambitious or content with settling for mediocrity? Is he hardworking or lazy? Does he value the work he does or just want to pay the bills and enjoy everything else? These are all questions that will be answered by asking him if he likes his job.
What’s the worst online date you’ve ever been on? Pretty much everyone these days has used a dating app at some point, which means that everyone inevitably has a dating app horror story. Not only is it fun to hear about other people’s dating nightmares, but it can also tell you a lot about their judgment of people and who they choose to go out with.
So, how do you think this date is going? This might terrify the crap out of him, but it may also catch him so off guard enough that he’ll give you an honest answer. You really don’t have much to lose on a first date. Being honest with each other could turn the night into a huge success (or allow for a quicker exit) instead of letting it be another boring, by the numbers routine like most first dates end up being.
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