5 Questions To Ask Him That Will Tell You Everything You Need to Know


Ah, the art of nailing the first date. The perfect outfit that says “Oh hai. I’m just over here, hanging out, doing my thang, looking good. You wanna know more, dontcha?” Flawless conversation that flows without hiccup. Gentlemanly gestures and fun with flirting. That first accidental glance of physical touch. Witty banter. Smiles and stares. Butterflies. The first kiss. Le sigh. The thing that brings home a fabulous first date is the conversation. To get from “Hi, my name is” to “Do you have plans tomorrow? I want to see you” requires a solid volley of genuine interest and chemistry-laden curiosity. Hot damn, I can feel it already.

This is also the point where red flags make themselves known.

All the red flags you will ever need to know will rise high and fast in the first moments of getting to know someone. You can def find a few (IF they are to be found, that is) on the first date. So, why not cover your bases while face-to-face? Here are a few questions that will reveal more than just your average “I’m a cat person.”


What’s your dream vacation?

People are very generally divided into two groups on this: beach or mountains. Beach could indicate relaxing, tropical, serenity, romantic, private, etc., while mountains could point to active, rustic, nature, thrill-seeker, outdoorsy. (Again, VERY generally speaking, obvs.) His answer will allude slightly to any common interest you two may share. The point is to parlay his answer into other questions about what else he likes to do with his life.

Unless you hate travel. And seeing new things. And tropical vacays. And romantic snowscapes. In which case, well, ask him what he likes to do on a Saturday night and pray for a “Play checkers.”

“What’s your ‘thing’?” is always good, too. I was just recently asked this, and despite freezing and not knowing how to answer (DUH, THIS BLOG), I realized it was kind of a cool way to pose the question. Music, art, film, fashion, travel, sports?


Are you passionate about what you do?

SO much better than “What do you do for a living,” right? This will launch an entire discussion about his job, his energy levels, his desires, what he strives to be, and maybe more. Unless he’s an emotionless wonder. Which, in that case, you still have your answer, don’t you?


If you didn’t have to work for a living, what would you do?

This starts to get at who this person really is and what’s important to him. Would he build an after-school program and work with children? Spend his days traveling? Not want to stop working? Fundraise for ALS? Write comedy? Or do absolutely nothing, sitting on a beach, drinking beers and scratching his balls.


Are you close with your family?

Sure, you can pay attention to his relationship with his mother and female siblings. But overall, getting to know whether he’s close to his family or prefers never to speak to them will shine some light on his attitude toward intimate relationships. Also keep an ear out for any familial ethos that he was taught to live by while growing up.


And the winner: What’s the one complaint every one of your ex’s would make about you?

Establish a flirty repartee before you launch this one, mmk? This is basically a twist on the classic “So, you seem perfect. WTF is wrong with you that I’m missing?” So I strongly suggest that, if you’re going to pony this one up, that you make sure you’re both feeling each other something fierce, so it’s not such a shock when he hears it. If he has a healthy sense of self-awareness, he shouldn’t be put off by this, but rather be highly aware of whatever shortcoming he’s about to divulge.

In general, if your dude can’t answer questions straight on, leads you down a ton of tangent paths that trip you up, or just flat out deflects and changes the subject, that’s not so good. You want a guy who can approach any situation, whether comfortable or not, with honesty and straightforwardness. Dodgy dudes are up to no good. These are flags you should be hip to.

What does a red flag feel like when it shows up? Dread. Straight up dread. An “Oops, welp, that’s not ideal.” That, Oh shi*t, feeling that says, this is going to be a problem.

Sometimes flags aren’t red, they’re yellow or orange (or rainbow…) which makes them seem less harmful and hit you a lil bit softer but can still stand in the way of a successful relationship. It’ll feel more like a “Hmm, this may not be a problem but it’s def gonna be an obstacle.” Up to you to decide if you wanna deal with that. Happy conversing!