The Best Questions To Ask Before You Start Dating Someone

A couple holds hands on a date, candlelit table and two glasses of red wine
Photo by René Ranisch on Unsplash

When in the beginning stages of dating, it's important to know as much as humanly possible.

The element of surprise is no longer a fun aspect of romance.

Ask the small questions. Ask the hard questions.

Interrogate. Grill. Investigate.

Of course, you should do it with a subtle hand instead of an interrogation lamp.

The truth is all we have.

Ask everything.

Redditor RedditPenguin02 wanted to make a list of the best inquiries to make when starting a relationship, so they asked:

"What is a good question to ask before you start dating someone?"

From what I've learned in my past, always ask... "Are you into Buffy the Vampire Slayer? The TV show."

If it's a no, then it's a dealbreaker.

I Do

Shocked Schitts Creek GIF by CBCGiphy

"Are you married?"


"I would ask that. If they said no, the next question was 'Would your wife agree?'"

"If they laughed, they were telling the truth. If they got indignant and pissed off that I thought they were lying…they were married."

"Worked every time."


We Lived!

"Do you clap when the plane lands?"


"I swear people used to do this all the time when I was a kid (early 2000’s), and I don’t think I’ve heard anyone do it in 5+ years. I guess 9/11 really made people afraid of flying for about 10 years and then most folks decided they didn’t need to applaud when the plane landed safely?"


Family Planning

"Do you want kids in the future? If one person wants kids and the other wants to stay child-free, then they are not compatible. And it is better to try dating someone else."


"It confuses me whenever some couples who disagree on this end up in a conundrum because one expected the other to change their mind. This is something I bring up early cause I see no future with someone who wants kids when I do not."


"You should always put childfree on your dating profile. It's not a small thing. Either you agree on it or not. If I had to date, I would put childfree on my profile too."


Carb it on...

"Do you like bread? That is the extent of my flirting skills."


"Being German, bread is like a frickin' cultural phenomenon here, we have around 300 kinds of bread, there's a bread museum, every time I go on vacation I'm like yeah it's nice here but the bread ain't it yall, never as good as home lol. So yeah, valid question and the only answer to this is an enthusiastic yes."


Room Temperature

Frosty The Snowman Winter GIF by filmeditorGiphy

"What temperature do you set the thermostat to throughout the year?"


"Haha this one always gets me as someone who needs low temps - you can always put on more clothes, I can't peel my skin off to get cooler."


The thermostat is a dealbreaker for me.

It's gonna be 60. Love it or move on.


Blown Away Wow GIF by AminéGiphy

"When was the last time you changed your mind about something?

"Opens a window to how they think."


"If that was really early on in the dating I’d think it was a bit of a head-f**k question. I’d probably find that question a red flag, tone dependent, although I agree with the sentiment."


Personal Time

"Aside from major differences about finances, kids, politics, or religion, a big one is; What are your hobbies? If they don’t really have any, you may be the next hobby, which isn’t going to work unless you’ve got that kind of time. If the hobbies are time-consuming ones generally done with a SO."

"But you have no interest in them, that could be an issue as well. If only one of you likes camping, wanted to spend vacation lounging instead of exploring, didn’t like sports, etc either that partner is annoyed or the other feels like they don’t get to enjoy what they love."


Past Issues

"Ask them about their exes. If they think every single one of them is an a**hole... they are likely the real a**hole."


"I have mixed feelings about that - I've been in three previous relationships and all three were emotionally abusive towards me (one wasn't nearly as bad as the other two, though) in various ways. I know this is a common sentiment and it always makes me afraid that people won't believe me or something.

"I mean, I realize in your comment you said 'likely' and not '100% sure' and there's plenty of room for nuance."



"I would try to take care of any dealbreakers. If I find out that she has different political values than I do, it's not going to work out in the long run, so I wouldn't bother. Same thing with other factors (religion, financial values, etc.). I would also ask how much cuddling she likes to engage in, as I prefer a lot."



Tell Me More To Do List GIF by Disney ChannelGiphy

"When I was dating my three essential questions were always kids, sex, and money. If you're not on the same wavelength for any of those three things, just don't even try."



"So, how much personal debt do you have?"

"Source: the guy who dated a woman with huge debts and was asked to pay for everything and then some".

"After that, I'd go with, 'Have you ever been diagnosed with borderline, narcissistic, or histrionic personality disorders?"


The questions are basic.

Just ask for the truth.

Do you have any good Qs to add to the queue? Let us know in the comments below.

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