Questions To Ask Your Boyfriend

Typical getting-to-know-you questions are a mainstay of dating now. Everybody knows you answer things in the polite, politically correct way to ensure a good date. It’s a bunch of fake crap and you aren’t playing around. Here’s slightly deeper, slightly manipulative and very strategic conversation starters disguised as questions to ask your boyfriend or a potential ditto.

 

Did you see that video where (insert current political candidate/celebrity) was doing (insert weird random story you saw on the opening monologue from Jimmy Fallon last night)?

It’s best to use a controversial person in this instance. Think Donald Trump, Kim Kardashian, that newly bisexual mom from Honey Boo Boo, etc. This one is a triple threat question: does he keep up with pop culture, is he willing to express an opinion and how does he feel about a controversial figure. If he hasn’t seen the latest viral video circulating television and the Internet alike, ask him how living under a rock is suiting him. Expect a strong reaction here- remember the controversial part?- it shows he has an opinion and is willing to express it wholeheartedly. That’s a good thing. Now for the actual opinion. Depending on your political leanings and feelings on reality TV, it’s up to your interpretation. If you can’t date a Trump supporter, at least you found out early!

 

How did you end up with the job you have now?

While I’m not promoting elitism, I am pushing you to think twice about dating someone without a serious education. If you’re looking for a long-term situation but he only has a GED, move on. The answer to this question will answer a lot of hidden ones: did he go to school? What major did he graduate with? Did he get this job on merit, through connections or ass kissing? This will be a good indicator of his character.

 

Who do you usually hang out with?

General and vague but also very telling. The first sign of a guy that probably wouldn’t be a good mate is a lack of friends. That’s not to say a small friend group is a bad thing- in fact, it’s probably a sign of maturity. I’m talking about the guys with zero friends. Or his only friends are online chatting with him through video games. It’s a red flag of some social problems that could easily translate into relationship problems. This question should also explain his typical social patterns- does he stay at home with beer and a movie or does he go out for the occasional adventure? Hold onto that answer for a later time to plan dates… he’ll appreciate the thought.

 

What’s your favorite drink?

This might seem silly, but a drink can say a lot about a person. The basic rule of thumb is the simpler the drink, the less fussy the man. A beer guy is laid back, probably a slob and likes to have a steady stream of football on the TV. A cocktail man is most likely full of himself, likes to impress people with his obscure drink orders and his mom still does his laundry. A man who enjoys the vino could be a variety of things: thoughtful, foreign or creepy. Use discretion with a merlot man.

 

What’s the worst date you’ve ever been on?

Here’s what you’ll learn: how much he’s dated, if he has a sense of humor, his pet peeves/turn offs, and what he considers a bad date. If it’s just a boring story about a girl that showed up 10 minutes late to dinner, he’s boring. Who doesn’t have a good bad date story? If it’s about a blind date showing up drunk off their ass with a stuffed animal followed by a midnight trip to Walgreens and a minor car accident, he’s probably got enough dating experience. Bonus points if he can tell the story well. Also, lay off the Manhattans on the first date.

 

Do your parents have a traditional dynamic? Man as the breadwinner, woman as caretaker?

His opinion on this will show how aware he is of the gender roles in his childhood. If he can’t identify those at the very minimum, you’re dealing with a child. Now, onto the answers: if he is adamantly pro-patriarchy for a household, ask why. Either he is very (very) traditional and has a rational explanation, or is a misogynist. The answer should be clear. If his answer is along the lines of my parents were pretty progressive, there was no clear-cut boss, he is most likely thoughtful about gender roles and an open-minded fellow.

 
Does this formula make sense? Create your own questions to dig deeper into your potential man’s psyche. Remember to disguise it as a general honeymoon stage question and he’ll never know what you’re up to.

 

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