Five Conversations to Have with Your New Partner in the First Month of Dating

When you start dating someone, that first month is a whirlwind of excitement. There’s the awkward first date (Do you hug goodbye? Would a handshake be weird? Who pays for the check?), the first kiss, the butterflies in the pit of your stomach.

It’s a heady mixture of lust, anxiety, and anticipation.

After all, you’re in the careful, getting-to-know-you phase and having fun – the last thing you want to do is have “serious conversations.”

But, that’s exactly what you need to be doing.

Okay, okay, maybe not all of the time (and maybe not all of the important conversations), but there are some things that you need to talk about. Five conversations to be exact.

So, before you consider going any further with your potential bae, here are the five conversations you should be having:

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Five Conversations to Have at the Start of a New Relationship

1. Your “Intentions”

Are you picturing The Bachelor? Good – now don’t imitate that.

While it’s always fun to watch the contestants with their inane drama, it’s certainly not something you want to bring to your own life. Still, they are on to something with the whole “What are your intentions?” thing.

I’m not saying that you should phrase it that way (in fact, it’s probably best if you don’t use those exact words) and you definitely don’t need to make it a big, dramatic production. But it is important to talk about what it is that you’re looking for.

Do you want a committed, monogamous relationship? Say so! Do you plan on casually dating for a while? Cool! Just be upfront about it.

While most people don’t (and, honestly, shouldn’t) start getting serious within the first month, it’s good to know at the outset what the other person wants. There’s no use going and getting all attached to someone who isn’t looking for more than a fling.

On the flip side, if you’re the one seeking casual relationships with multiple people, you don’t want to mislead anyone. No one needs that kind of karma.

2. Your Relationship History

Ah, the old “what’s your number?” question. You know – the one that secretly begs the question, “Do I need to get tested after you?”

In reality, for some, it might be really important to know how many people their partner has been with, but for others, the actual number isn’t all that relevant.

Either way, if you’re not interested in revealing how many sexual partners you’ve had, you certainly don’t have to.

What you should talk about, however, is your relationship history.

Are you just getting out of a serious relationship? You might have some baggage still – nothing wrong with that, but it’s something your partner should be aware of.

Again, you may or may not want to ask your partner about their “number,” but you’ll want to ask them how serious their last relationship was and why it ended.

There’s a LOT that this conversation can tell you about your potential mate. For example:

  • Have they had a lack of serious relationships in their past?
  • Do they maybe have some commitment issues? (ahem, Brad.)
  • Do they blame their ex for everything?
  • Can they take responsibility for their faults?
  • Do they seem like they’re still bitter/heartbroken/angry?

You probably also want to know if your partner is friends with any of their exes. If they are and you’re not aware of it, it’s likely to cause some speed-bumps down the road.

3. Your Expectations in a Relationship

This one might seem a little odd – after all, you’re not actually in a relationship just yet. But, hear me out!

Everyone has different expectations and wants in a relationship. Talking about it will help you find out how compatible you are with your partner. Not to mention it’ll probably help prevent unnecessary arguments later on.

For instance, some people might be OK with seeing someone they’re casually dating once or twice a week. That same person, though, might expect to see someone they’re in a relationship with four or more times. Helpful to know right?

Same can be said for infidelity – maybe you don’t consider it cheating unless you actually have sex with someone else. But if your partner thinks kissing is a form of cheating, that’s something the two of you need to be aware of.

4. Your Sex Life

Obviously, if you have any sort of STI, that’s something your partner needs to be aware of before you actually sleep with them.

Your sexual lifestyle should be disclosed as well. If you’re seeing (and potentially sleeping with) multiple people, you should be upfront about it.

But what about your views on sex? Are you someone who only has sex once commitment is involved? Or maybe you’re the opposite and you don’t agree to monogamy until after the deed is done. What about how important sex is to you? Do you want to have sex multiple times a week in a relationship, or are you a once-a-month-is-fine type?

On a similar note, it’s helpful to know upfront what kind of sex life you’re wanting in a relationship. Maybe there’s something you’re really into – like BDSM or role-play. Let your partner know what it is that you like!

Finally, do you have any, ahem, issues in the bedroom?

Men (especially those of a certain age) might have difficulty in that area. Nothing to be ashamed of, but tell your partner if that’s the case.

Women, too, often have difficulty reaching orgasm. If that’s you, be sure to let your partner know what it is that you need to get off. Or let them know if an orgasm isn’t really your end-goal during sex. There’s no need to fake it – just be honest!

5. Your Goals in Life

This one kind of goes hand-in-hand with what you’re looking for in a relationship, but let your partner know what it is that you’re wanting in your own life.

For example, if you’re planning on spending a year or two abroad but the person you’re dating has kids/a steady job/a mortgage and isn’t interested in moving out of the state, that’s a problem. If you want to live in the city but your partner wants a McMansion in the ‘burbs, you need to know upfront before you get any further invested.

And what about your long-term goals? Do you want to get married and have kids one day? Your partner may be looking for a serious relationship, but they may simultaneously be staunchly opposed to marriage or parenthood. Or maybe they’ve already had kids and aren’t interested in having more.

Even if two people both want something serious – and even if those same two people have an amazing connection – they might not be compatible for one another.

That’s why talking about what you want your life to look like is so important. This will help you determine how well matched you actually are.

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Conclusion – Five Conversations to Have at the Start of a New Relationship

So, there you have it! My take on the five conversations you need to have within the first month of dating.

Now, go forth and talk it out. And be sure to let me know your thoughts in the comments below!


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  1. avatar

    This is awesome – I agree that it’s so important to have these tougher conversations early on before things begin to become serious. In the moment they always feel awful, but afterwards, I always felt so so so much better and lighter knowing where everyone stood! This post is going to help so many people – thanks for sharing this great list.

    1. avatar

      I absolutely agree! It’s better to find out early on whether or not there’s even a potential there than to waste more time.

  2. avatar

    Yes. Love this post! So many people tell you not to have serious conversations too early but it’s like why waste time with someone who isn’t interested? Or doesn’t want the same things as you? I think speaking about last relationships is so important because personally I feel like that’s where you tend to find the red flags haha!

    1. avatar

      That’s so true! Learning why someone ended their last relationship and whether or not they can take some responsibility for it is incredibly telling

  3. avatar

    A very helpful post indeed for those who have started dating. It’s so important to get these topics spoken about and out of the way at the beginning. It lets you both know if you’re on the same page or not. I once had a relationship where we had a honeymoon phase but 8 months in it was very clear we both wanted very different things from life and I always wished we had taken the time to have proper conversations at the beginning.

    1. avatar

      Yes, exactly! It’s so easy to get swept up in chemistry and romantic attraction, but sooner or later, you have to find out whether or not you’re compatible. I’ve had some very similar experiences and it always sucks to find out later on.

  4. avatar
    JoJo Hall says:

    Awesome post! I think people tend to be so lovestruck and caught up in the moment of dating that they forget to have these important conversations in the beginning.

    1. avatar

      Exactly! Could not agree with you more.

  5. avatar
    Charlotte Birchall says:

    Love this post. Such great information, it is well the read. Thank you for sharing.

    1. avatar

      Awe, thank you so much! So glad that you enjoyed it!

  6. avatar

    Such an informative and widely impactful post. Indeed it’s better to have real interactions with regards to how to carry out each other’s life. That actually gives an individual a more clarity about a person whom we are suppose to spend the time during the life. Really it was worthy read. Thank you so much for sharing!

    1. avatar

      Thank you so much! I’m glad you found it helpful.

  7. avatar

    These are excellent questions! If the object of your affections can’t handle the third degree, you probably should call that a red flag.

    1. avatar

      Exactly! They should be able to have these conversations easily if their intentions are good.

  8. avatar

    This is such an educational, honest and insightful post! I love how you described the awkward first date perfectly as well. Many skip over effective communication, which can cause problems later on in the relationship. Better to have the awkward conversation now than enter a stage of confusion later.

    I love all these tips, and my current partner and I discussed each one early on in our relationship.

    Thank you for sharing your valuable advice! ?

    1. avatar

      That’s fantastic! You’ll have to let me know how it shaped your current relationship!

  9. avatar

    This is such an insightful post. It is awkward having these conversations, especially early on when you are just getting to know someone, but they are crucial. Simple communication like this can save people a ton of time and heartbreak since without talking about these topics, they could end the relationship down the road. I always enjoy your posts, keep it up!

    1. avatar

      Awe, thank you so much! I love hearing that. ❤️

  10. avatar

    You nailed it with this post! This is a great guide for someone on the dating scene. Intentions and goals are definitely important and must be discussed early on. Who wants to waste time?

    Your advice is so helpful.

    xo Erica

    1. avatar

      EXACTLY! Time is too valuable to waste on those who aren’t going to be able to meet your needs ?

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30ish Lifestyle blogger, relationship "expert," and modern-day agony aunt.
Sometimes humorous, always honest.