5 Questions You Should Ask a Guy Before Getting Serious About Him

So, you're thinking about getting serious...

Most of you have heard of some big questions to ask your date before getting into a serious relationship. Often, they include “Are you looking to get married?” and “Do you want kids in the future?” or “What’s your five year plan?” Those topics are popular for good reason. And most people already know to ask them.

So today, let’s mix it up a bit and explore some less well known topics. Unusual? Maybe. But they are definitely worth exploring before getting serious about romance with a new fellow. (And as always, be prepared to answer the question turned around back at you! It’s only fair to play your own game, after all.)

Are you an early bird or night owl?

This is a fun way to lead into discussing lifestyle patterns. Generally, most healthy people have a decent balance between getting up early and staying up late. But that doesn’t mean you should write off anyone who doesn’t match up with you. Instead, use this question to learn about what his typical workday and his free days look like. Is he on a night shift job? Does he always get up at five in the morning for a workout? Does he relax by sleeping in, or by staying up late?

You can learn a lot about someone by their sleep habits. You might discover he has great self-discipline and a rigid schedule, or you might discover he has a flexible personality that allows him to successfully pull off swing shifts or remote work. Occasionally, you might run into a concern, such as regular all-night partying. Wherever this conversation leads you, it has the potential to lead into swapping funny stories as well as insightful information.

What makes you take a sudden day off from work?

This question is highly personalized to individual situations, which is exactly what you’re looking for. Dating is a very personalized game, so start looking for the “why” behind your new fellow’s actions. This question has the added perk of learning more about your date’s job of choice, and what type of relationship their personal and professional lives share.

A doctor might qualify only emergencies as a reason to take a day off from work. Someone who’s had a bad week working in victim’s advocacy or caring for special needs kids might need to take a break to refresh their own mental well-being. You could also be looking at someone who takes days off just-because, or who never takes a day off no matter how sick they are. Listen to his stories to get a read on how he views his work, as well as what he prioritizes over it. Then, share your own!

What does safety look like to you?

This is a gentle way to inquire about his “protect and provide” instinct. Men are hardwired to be both more aggressive and protective: aggressive towards threats, and protective toward women and children. What does your date think about safety in his life? You can ask him where he draws the line in things like driving fast, if he’s ever called the police and why, or about times he’s run into a stranger who really needed help. He might surprise you with his situational awareness, logical thought patterns, or quick action.

Maybe he’s got some hidden gems up his sleeve like CPR training, survival skills, or jujitsu lessons. Perhaps he thinks ahead and carries a multitool, has a bag of emergency supplies in the trunk of his car, or has memorized helpful information like road maps or phone numbers. Who knows? You can learn all sorts of things about a man based on his safety awareness, as well as what levels he will go to take care of his loved ones.

What is your experience regarding pornography?

Yes, the pornography topic needs to be brought up. This one is no fun to talk about, but it does have to be addressed. It is an option to ask straight up whether someone uses pornography; introducing it this way runs the risk of the other person feeling that they’re being given an ultimatum.

If you word your question more open-ended and with room for the other person to explain where they are or what they’ve been through, you are creating a much more personalized and understanding environment. This question is not, I should add, intended to be a pass/fail pop quiz for your date. It is merely a way to open the topic and give rise to meaningful information. What you both decide to do with the information is another matter entirely.

What are your habits with drinking alcohol, smoking, video gaming, using social media, etc.?

The pornography question is pretty cut and dry, but there are lots of other gray areas regarding other habits. There is potential for addiction with alcohol or cigars, but they are not inherently evil, unlike pornography. Plenty of people enjoy Instagram or play video games without it impacting the rest of their lives. And there are others who struggle with pervasive habits which truly do affect those around them.

The purpose of asking questions about these things is to learn about this man’s lifestyle, and how he implements self-discipline when it comes to indulgences. Another way to reflect on his answers is to compare them to your own habits and lifestyle. Are you similar in your views and habits, or are you vastly different?

Now for the elephant in the room.

How do you ask these questions without scaring people off?! First, do your best to work these into a natural conversation. Dating is not supposed to feel like an interrogation, after all! Second, flip the script. When would you feel comfortable if he asked you these questions? Your timeline should match your own comfort levels in that scenario.

Finally, have a general idea which of the topics are most important to you. All of them can lead you into different conversations, and reveal different things about your sweetie. If you prioritize what you want to know first, it helps take the pressure off trying to ask everything all at once.

Above all, make sure not to fall into the trap of predetermining the answers you are looking for, and holding out for someone exactly like that. Remember, everyone is an individual with different lives and experiences, just like you!