50+ Questions To Ask Before Dating

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We talk a lot about the questions to ask when dating, but what questions should you ask before dating someone? What should you find out – in advance – before you choose whether or not to explore things romantically with them? And what essential questions should you ask YOURSELF before dating someone new? Well, let’s start from the top, shall we? Here’s 50 fundamental questions to ask before dating, so that you cover all bases…

Why You Should Ask Questions Before Dating

So first off, why should you ask – both yourself and your potential date – questions before dating? After all, isn’t it a stage that is often overlooked or missed out? Well yes.

And this is for a number of reasons:

See, nowadays, you can join a dating app in minutes. It’s fast, easy, and pretty tempting…

Especially if you’re still hurting after a breakup and want to take the pain away, or are feeling lonely being single and looking for a quick-fix.

Similarly, when you’re then on those dating apps and are speaking to your “matches”, you’re all on the dating app for one reason… To date. 

But not often enough, do people take a step back and ask themselves, 

  • Do I want to date this person? 
  • Should I actually date this person? 
  • Do I see this progressing on a romantic level, to the place where I’d ultimately want it to go?

Because sure – you may ask yourself if you want to go on a date with them. But you probably don’t look much deeper… 

Whereas if you did, and you asked more “deal breaking” questions before dating, you would end up saving SO MUCH TIME, and probably a fair bit of heartache (on both sides) too!

Should we date?

Questions To Ask Yourself Before Dating

So, let’s start from the very top, shall we? What questions should you ask yourself before dating? 

(These are not specific to a person and deciding whether or not you should date them, but are instead about whether dating in general is right for you at this stage.)

Of course, not all questions in each category are essential to you…

That’s why you need to pick and choose the ones that are, then ask yourself those. Or, use them to inspire other questions you know you need to ask!

If You’ve Recently Been Through a Breakup…

Some of the fundamental questions to ask yourself before dating, include:

1) How do I feel in myself right now?

2) How does the thought of dating, make me feel?

3) Why do I want to get back into dating? What’s the honest main driver here?

4) Why would I possibly NOT want to get back into dating just yet?

5) Or what reasons would there be why I perhaps SHOULDN’T date again just yet? What arguments could there be for why it’s too soon?

Let’s Keep Them Coming

6) Can I genuinely say I feel READY to date again? And what does being “ready” mean, or look like, to me? How do I know for sure?

7) What is my purpose of dating right now? How should I go into this?

8) Are there any things I need to do or say, to ensure that my dating experiences are as positive as they can be? How can I give myself the best chance of this working well here?

9) Are there any “rules” or guidelines I need to give myself here?

10) What standards and expectations should I have, should I choose to start dating again? And how will I make sure that they’re stuck to?

Am I ready to get into something new?

If You’ve Been Single / Dating a While…

Some of the fundamental questions to ask yourself before dating someone new, include:

11) How do I feel in myself right now?

12) Am I dating a lot or a little? And could this be too little or too much?

13) Why am I dating? And am I dating for the right reasons?

14) How would I feel if I stopped dating completely, or had a “dating ban” for a month or two? Could I do it? (And this includes not being able to match or speak to new people.)

This is important as it reveals any dependency on dating to combat loneliness / a lack of love. Ideally, you want to reach the point of being happily single before you actively date to find someone new.

15) How do I feel when dating? Am I having more positive or negative experience? And overall, am I enjoying it? Do I see it as fun?

What Else Have We Got?

16) What lessons can I / should I learn from my dating experiences so far, that I should remember / bear in mind, moving forward? This is another big, important question, so really think it through.

17) Is this working for me? In what areas could I improve my “dating game”? And what things am I still not sure about? What things could I focus on expanding my knowledge on, when it comes to dating and how could this benefit me?

18) How can I make dating MORE fun or enjoyable?

19) What’s stopping me from dating more? What’s holding me back here? (Try to identify any fears you need to work through.)

20) How can I date smarter or more effectively, to ultimately increase my chances of finding – and keeping – the kind of person I want in my life?

See, if you’re already dating, it’s a good idea to take a step back and reflect – evaluate.

It’s very easy to fall into the habit of dating and dating and dating. But that’s when you miss the slight adjustments you could be making, to make it work better for you.

For this reason, it’s a good idea to stop and use these questions to ask before dating, to ensure you fall into healthy patterns, as opposed to damaging – or at the very least – less effective ones.

Am I ready to start dating?

Questions To Ask Before Dating

So now we’ve covered the questions you should ask yourself before dating, what are the questions you should ask a potential date, before agreeing to go on a date with them?

See, ultimately, your questions to ask before dating, will be unique to you. (After all, you’ll know what is and isn’t important or a deciding factor…) But to help you determine what these questions should be, we’ve got a few more questions for you, first!

So, ask yourself:

21) What is my current situation with this person? Are we just friends right now? Have we been friends for some time? Do we work together? Have we just matched on a dating app?

NOTE: Being friends before dating someone isn’t such a bad idea. In fact, studies suggest that 68% of romantic relationships actually start from budding friendship (apparently!) So it’s a pretty common thing.

22) How well do I know them? And have I taken the time to properly get to know them on a deeper level? Have I asked more personal questions or qualifying questions? On a similar note…

23) How well do I align with them? Have I asked them, key questions, relating to the things that are really important to me – to see if they’re on the same page, or can agree?

Let’s Keep Them Coming

24) Is there anything that I’m overlooking here? Are there any “red flags” or potential problems that I’m ignoring because I WANT to date them, but know – deep down – that it probably won’t work out?

25) Am I letting my fears get in the way here, or coming up with excuses not to date them, because I’m scared of [this] or [this]?

(The better you know yourself and your habits and how you typically behave, the easier this question will be!)

26) What do I think of them? Do we get on well? Would I probably have a good time with them?

27) Do our feelings – at this stage – seem fairly balanced, so there’s less chance of one of us getting hurt if we did open our hearts to dating each other?

Or – at the very least – have I been as honest, open and transparent as I can be, so that I’m not leading this person on, and I’m confident that they wouldn’t do the same with me either?

28) Could I potentially see them romantically? Or do I already see them in that way?

If not – what’s stopping me from seeing that romantic connection right now and how likely is this to change? (E.G. There are ways to find someone more attractive, you know?)

29) What would be the BENEFITS of going on a date with them?

30) Are there any reasons NOT to go on a date with them?

Questions to ask before dating

Questions To Ask Before Dating

The above questions should now help you to better determine the questions to ask before dating. For example, if you’ve asked yourself:

“How well do I align with him?” it may then lead you to think:

  • “Well I know we’re on the same page about [this.]”
  • “And I’m happy he feels this way about [this.]”
  • “But [this] is important to me, and we haven’t spoken about that yet…”

You will then come up with UNIQUE questions to ask before dating, that are relevant to you and based on what you already know about the person you’re considering dating, or need to know before deciding whether or not to take the next step on that romantic level. You see?

Now there are of course, some common questions to ask before dating, that – as a whole – most people want to know. So to finish off, we’ll give you some template messages.

(Uh huh, you’ll be more-than prepared after this, right?!)

Questions To Ask Before Dating (Templates)

Last but not least then, here’s our template questions you may like to pick and choose from, to ask a person before deciding whether or not you want to start dating them.

See, there’s plenty of dating app questions to make conversation fun and entertaining, but these questions to ask before dating, are more focused and specific.

Remember: this isn’t an interview so don’t ask all of these questions in one go! In fact, you want to drop them in as casually and conversationally as possible. 

But some things that may be important to know, include:

31) So what are you looking for right now? (Do they want something serious, or are they not ready for a relationship just yet? And how – more importantly – does that tie in with where you’re at and what you’d want?)

32) Do you feel like you’re fully over your past relationship? You’ve fully healed? And which point did you know that you were ready to start dating again?

(As the last thing you want to do is get involved with a guy who’s not over his ex! This question is especially relevant to ask before dating if the guy hasn’t been single for very long…

Protect yourself, and your heart. You’re not there to be a rebound relationship. No way!)

Let’s Keep Them Coming

33) Why did your last relationship not work out?… If you don’t mind me asking!

(This isn’t an essential question to ask before dating but it is insightful. It also backs up whether or not he’s over his ex, as – ultimately – he should know why they weren’t right for each other.)

34) Have you dated much? What’s your dating history like?

(Without going into all of the “gory” details of course! Questions about dating can be really fun and relatable however… not to mention, insightful too!)

35) You think that us dating is a good idea, then?! (Say it casually, but it’s good to get his perspective – verging on “sales pitch” – on it, for sure!

This may also help you to confirm in your mind that moving into the dating stage is a good idea, so it’s a great question to ask before dating.)

Do I see him romantically?

Questions To Ask a Guy Before Dating

36) What’s your idea of a perfect first date?

(Talking about what it COULD be, before making any plans or commitments, can help to get you excited about it, as opposed to “fearing” it, if that’s one of the things that is standing in your way.)

37) How do you think things would change if we started dating?

(This one you can say fairly jokingly, but you can then gage how casual or intense it would be… And then make a decision as to whether you’re comfortable with that. Similarly…)

38) Do you like to take things slow when dating? And what does that mean to you?

(You want the right balance between things moving at the right pace, but the person still being proactive and clearly interested in pursuing you… Because they know your value and see real potential here!)

What Else Have We Got?…

39) Do you find falling in love scary, or exciting? Or BOTH?! And why?

(This is a great question to ask before dating, mostly because it gets the two of you opening up and having a heart-to-heart about things that could actually make you feel quite vulnerable.

It brings you closer and helps to build trust from the get go. On that note…)

40) Do you find it difficult or easy, to give your trust in a relationship? And how do you think trust is best built?

(These can be a little more testing questions to ask a guy before dating, but it’s interesting to hear his views and ideas… Plus how clued on he is when it comes to these kind of conversations. Building into these further…)

Important Questions To Ask A Guy Before Dating

41) What would you say your communication is like when it comes to dating & relationships?

Do you find it difficult or easy to communicate? And what about when it comes to expressing your feelings or emotions?

(This helps you to understand him better which will then make your new relationship far easier to navigate.)

42) Do you know what your attachment style is? Or your love language?

(Both of these aren’t deal breakers as such, but again – show how well you will gel and make him / her easier to understand!

It’s not an ESSENTIAL question to ask before dating – you will no doubt find out these things later down the line – but can be a good one!)

43) What are your dating and relationship standards or expectations? What sort of things do you feel strongly about in terms of what is and isn’t right?

44) Do you have any dating / relationship deal-breakers?!

(Again, have fun with this one. You should also share your own.

This is an important question to ask before dating as there’s no point getting into something if you know that there’s some big things that make the two of you, not right for each other.

In this case, you’d just be better off as friends!)

Questions to ask before dating

Deep Questions To Ask a Guy Before Dating

45) What are your goals, or aspirations in life? What things do you want to do, achieve or have? And why? What’s important to you and what drives you?

(Don’t ask this as a question which determines whether or not you’ll go on a date with him / her… I mean, how judgemental would that seem?!

But it will – of course – tie into things, as you do want to find someone looking for the same things as you!)

46) What’s your relationship vision? What kind of relationship do you want to build & have? And what do do you think makes a GREAT relationship? Plus how do you go about building that?!

47) Do you want kids? How important is building a family to you?

(Note: You may want to ask specific questions like this, based on the things that you know you want – or don’t want- and which are important to you.

This goes back to the deal-breaker questions to ask before dating, again!)

Onto The Last Ones

48) How have you changed or grown in the past year? (Self-awareness is always a good sign, as is development. This may be important to you if you’ve been on a similar journey too.)

49) What does loyalty mean to you? What do you think it means to be a loyal person and what does that take?

(You’ll probably be able to gage his loyalty, even now, by how he treats both you and other people. This question can also lead into discussions about cheating if this is something that worries you before getting involved with a person. Last but not least then…)

50) How do you go about dating? Do you date multiple people at the same time? Do you have any “rules” or “expectations? Let’s talk about that! (This can help you make the final decision!)

That’s All For This One

So there we have it – 50+ questions to ask before dating, including some key, essential questions you really should be asking yourself (and others) before exploring something new.

Remember, each person’s “essential” questions will vary. But this should give you plenty of ideas for how to determine yours, and what exactly they are.

I hope this has helped.

See, this isn’t about being SCARED of dating – it’s just about making sure it’s the right time, you’ve got the right mindset around it and are then investing your time in the right people.

Take care. Wishing you all the best.


Questions to ask before dating
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Ella Stearn
Ell is a Breakup, Dating & Relationship Specialist & Coach, with over 3 million annual readers, globally. As the Creator of Forgetting Fairytales, her mission is to help you learn to love yourself, find the right person to give your love to, then make it a love that truly lasts.

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