52 Best Questions To Ask Someone Before Starting Dating Them To Save Yourself From Problems Later On

It’s essential that couples are on the same page in order for their relationship to flourish. If your and your partner’s values, goals, and daily lives are compatible, you’ll probably have your Happily Ever After. However, if you’re misaligned, the odds are that things will eventually end in tears and heartbreak. So it makes perfect sense to get to know someone before committing to them just because they have beautiful eyes or they were nice to you that one time.

Redditor u/RedditPenguin02 sparked an interesting online discussion, as people shared what questions it might be a pretty good idea to ask someone before starting to date them. We’ve collected some of the best ones—from the super serious to the slightly silly—to share with you. Scroll down to check them out!


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

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Are you married?

Squibit314 replied:

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.

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Do I like them, or do I just like that they like me?

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Unfortunately, just because someone gets married doesn’t mean that it’ll be for life. Divorce can be a very messy and expensive affair, especially if the couple is no longer on even semi-friendly terms with each other.

Divorce rates in the United States are staggering. Psychology Today notes that around half of first marriages end up in divorce. Meanwhile, the rate is even higher for second (67%) and third (73%) marriages.

However, Forbes points out that the divorce rate has dropped from 4 instances per 1,000 people in 2000 to 2.5 per 1,000 in 2021. The marriage rate has declined as well, from 8.2 to 6 in that same timeframe.


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.

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

Opens a window to how they think.

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How's your relationship with your parents?

This speaks volumes about many people.

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“One common explanation for the failure of second and third marriages is that a significant number of people enter a second or marriage on the rebound of a first or second divorce. Often the people concerned are vulnerable; they do not allow sufficient time to recover from their divorce or to get their priorities straight before taking their vows again,” Mark Banschick, M.D., writes on Psychology Today.

According to the divorce expert, some people may not have “internalized the lessons of their past experience,” and so they’re likely to repeat the mistakes from their past relationships.


“What are you looking for in a relationship?”

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Do you want kids in the future?

If one person wants kids and the other wants to stay childfree, then they are not compatible. And it is better to try dating someone else.

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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.

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At the core of pretty much any long-lasting, healthy, and happy relationship you’ll find two people who love, trust, and respect one another and are deeply attracted to each other. They’ll be very open with each other, communicate often, and will draw healthy boundaries. 

And you can’t get there without a lot of compatibility. It’s essential that both partners have the same expectations when it comes to the big questions like having kids, getting married, what kind of lifestyle they want to lead, and in what part of the world they want to settle down, etc.


Probably questions related to spending habits and how much "stuff" they like to have. Poor financial management and hoarding are crushing factors in a relationship.

The older guy of a family in the neighborhood died near the beginning of the year. The wife was moved to assisted living last month, and they took one large uhaul of stuff out of the house, and then I'm told the house flippers loaded 6 (yes SIX) large (40 cubic yard) garbage dumpsters of hoarded... stuff... out of the house.

Don't be that family. Run away from people with tendencies like this. You will be unlikely to ever cure them of it.

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Do you clap when the plane lands?

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Do they have any pets?

You can tell a lot about someone from how they treat and care for their pets, most of the time.

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But the smaller questions can reveal a lot about a person’s character, aspirations, and worldview, as well. And you can slowly start forming that picture by figuring out what someone does in their free time, what they’re passionate about, whether they tackle or avoid chores, and what their relationships are like with their family and friends.

Of course, you won’t get the full picture by talking alone: anyone can lie and flash a charming smile. So if you want to figure out whether someone’s worth dating or not, it might be a good idea to… go on a few dates with them. To put it simply, the more time you spend around them, the more you’ll see ‘the real them,’ not the image they project to others. It’s the small details, like how they treat waiters, how they behave when people are around vs. when it’s just the two of you, what they do when they’re fully relaxed, that will give you a deeper understanding of their strengths and flaws. 


Ha Ha, these questions reveal more about the questioner than the answerer. I think maybe we should also ask, "What questions when asked by a potential date, are red flags for you?"


While many may not agree with this very direct method if you are truly trying to find a long-term match and not waste either person's time talk about the big-five as soon as possible. My husband and I had the talk on our second date. We've been together since 2015.

The big5 are:

* religion
* politics
* children (to have or to have not)
* finances
* deal breakers: human rights / personal ethics concerns etc.

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How did your last relationship end?

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Are you jealous or possessive?

Seriously, people who are, it is better not to give them time to enter your life.

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Toilet paper over or under?


BIRTH CONTROL. And never believe "I don't take it because I can't get pregnant". Nature... finds a way.

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So, how much personal debt do you have?

Source: 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?"

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Do you have mental illness? If so, do you manage it?

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Do you believe in astrological signs or spirit animals?


Are you still living at your parents house?

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Do you like bread?

That is the extent of my flirting skills.


"Are you going to be financially dependent on me?"

I wish I'd known that with literally all of my relationships after I turned 18.


How do you feel about a woman's right to be a fully autonomous person?

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Do they have a criminal history or any addictions you need to know about.


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

djdante replied:

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...

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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.

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Are you religious? How religious? I’m agnostic. I could date a Christian, but after decades in a very high demand religion, I couldn’t be involved with anyone who was devoted to religion.


Do you have kids?

I asked that once and she said no. Then later after finding out she had kids, i confronted her about it and she said she didnt want to scare me off.

She got so offended when i asked “so you lied instead? I cant even trust you now.”


What they do to handle stress (genuinely), if they are in any other relationships, and if they have the same intent in dating as you. Nothing worse than finding out four years later that he thinks he’s poly and never thought you needed to know.

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I highly encourage you ask someone you are getting to know what they are excited about in the next few weeks or month.

For me, it's critically important that the people I dated were optimistic and excited about life. Obviously that's not mean to disparage mental health struggles. But it was important that I dated someone who had a similar mindset to myself. I'm someone who finds things to be excited about. I find it jarring and off putting to date or be close to someone who can't identify things they are excited about. They don't have to be big things. But having a sunny, positive, and agreeable disposition is important - at least in my opinion.

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Children, want them? Adopt? Already have them?

Religion/spirituality. For a lot you have got to be the same sect and church.

In my experience, this has been the biggest 2. Sure ther issues came up in previous experiences but they were a build up of issues. But only those 2 were big deal breaker where otherwise great chemistry wasn't enough.

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Are you pro-life? If I get pregnant, are you going to try to force me to give birth?

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Where were you on January 6, 2021?


For me, it was knowing if my now current partner was a picky eater. Could not handle that again if they'd have said yes.

Turns out he's the complete opposite and is more pig like as he'd eat anything, and probably your hand if you left it around his face for a minute.

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I have a set of questions like "where would a giraffe wear a tie? At the top or the bottom of the neck?"

The actual answer does not matter but I think that how they approach the question and how they defend their answer tells me a lot about them

Edit: Also to discuss

- how would a dog wear pants? 2 or 4 legs in?

- is a hot dog a sandwich? (I usually have to explain the cube theory for this one)


Do you have a social life that is fulfilling for you, do you expect me to be your social filler for when you are bored and want me to give up my active life to coddle you.


What motivates you?


Ask them what their hard demands, and hard no's are for a long term relationship.

Find out if even your most basic boundaries matchup/align.

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Do you have any foot tattoos? It’s been a red flag for me twice now.


I’m divorced after an 11 year marriage where the last 5-6 years my wife and I barely had sex at all. She was also abusive. After I went through my post divorce man wh*re stage for a couple of months I decided to actually look for a partner again. I’d talk with potential partners for a week or so before going on a date to make sure our sense of humor and personalities were a match. I was in my mid 30’s and a lot of the women I was talking to were divorced as well. If I thought we might work out I would ask about their sex drive and how often they wanted to have sex after the honeymoon phase was over in their previous relationships. It was a really big deal for me because I never wanted to live like that again. I ended up finding a wonderful woman who has a f****d up sense of humor who’s just as horny as me. The last 2 years have been amazing and we’re the happiest we’ve ever been.


Would you still love me if I were a worm?

MissFox26 replied:

My husband told me he would still love me and would carry me wherever he went in a terrarium. If that’s not love then I don’t know what is!

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"Do you actually like me, or just the idea of me?"

Alukrad replied:

I like this question but it's too direct to ask it that way. I think there has to be a more tactful manner to ask it.


What their definition of cheating is.

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Ask yourself: What is my goal in dating this person?


Before a first date: What are you looking for in dating right now?

Before getting in a relationship: Do you want kids, what kind of life do you want ten years from now, where do you want to live, what's your family like, how do you see finances between couples, how do you look at money/finances, are there things I need to be aware of, how often do you like to be intimate, do you want pets, how does religion play a role in your life, thoughts on drugs/alcohol/smoking, what do you value, what do you like to do for fun?

Before moving in together? What do you think is a good way to split chores/bills? Which furniture stays/goes? How do we give each other space? Do we get pets? How do we help support each other? What do we do if this doesn't work out?


Before starting a romantic relationship with someone, it's important to get to know them and understand their values, interests, and goals. Here are some good questions to ask before starting to date someone:

What are your long-term goals?

What do you enjoy doing in your free time?

What are your views on important topics such as family, religion, politics, or career?

What are your expectations for a relationship?

What are your deal breakers in a relationship?

What are your strengths and weaknesses?

What is your love language or how do you like to show affection?

How do you communicate in a relationship?

What are your thoughts on monogamy?

Have you ever been in a serious relationship before?


What kind of music do you like? What media do you enjoy consuming?


Are you friends with any of your exes?


Do you smoke?


do you have a history of mental illness in your family?