Difficult conversations are an unfortunate part of relationships. So today, I’ve got some advice on how to handle those difficult conversations with your partner.

Talk it Out: Advice on Having Difficult Conversations with Your Partner

Hello, again! And welcome back to another segment of Dear Dating Bitch, my online advice column where I answer questions submitted by readers.

Today, I have three very different questions that range from determining whether or not you’re “official” yet to handling hurt feelings in an open relationship. But despite the differences, these letters all highlight the importance of communication in relationships. Every relationship requires difficult conversations at times, and it’s important to learn how to have those difficult conversations with your partner in the right way.

Related Read: How to Have More Effective Communication in Relationships: A Guest Post

So, let’s get to the advice, shall we?

Dear Dating Bitch - How to Have Difficult Conversations with your partner
*Note: questions may have been edited for length/clarity.

Dear Dating Bitch is my online advice column. Submit to me here (don’t worry, it’s anonymous!)

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Q: I have been seeing this guy for just over a month and I’d like to know where we stand. I tried to broach the conversation gently because he is super shy and he got really squirmy and uncomfortable. He said he likes me and wants to see where things go.

How do I get a more straight forward answer or know if we are together officially or not?

Are we there yet?

Dear Are We There Yet:

First off, I’m not entirely sure what being shy has to do with anything. Was he too shy to go out on dates with you for the last month? Or to interact with you during those dates? Has his shyness interfered with any sort of physical intimacy between the two of you? Probably not. So don’t let him use that as an excuse to avoid difficult questions!

As much as I want to give him the benefit of the doubt, it seems like a red flag to me that he became “squirmy and uncomfortable” when you tried to gently broach the topic. Now, granted, a month isn’t a super long time so maybe he isn’t ready for the “relationship” title just yet, but if that’s the case, he needs to be upfront about it.

But so do you, my dear! I’m sure your intentions were good, but I think you can drop the gentle approach now.

You want a relationship with this guy, and being in a relationship means learning to have difficult conversations. So, the next time you see him (this conversation really should be done in person), be direct and set an expectation for him to do the same.

You: Guy, I’d like to talk to you about where this is going. I feel like I’ve tried to bring this up before, but maybe I wasn’t clear enough. I’m looking for a relationship and I’d like to know if that’s something you want too. I don’t want to make you feel uncomfortable, but I would like some clarity on where things stand.

Another option here is to ask him point blank ‘Are you seeing other people?’

He should be able to answer either of those questions in a straight-forward way, but if for whatever reason he doesn’t, I would push for it. You can do it nicely, but remember to be firm.

As a side note, I wouldn’t date anyone longer than 3-4 months without getting an official title.

Related Read: Five Conversations You Need to Have In the First 30 Days of Dating

Q: What do I do to help my boyfriend be less vanilla during sex? I’ve tried offering suggestions and he always shuts me down.

Does this mean I’m bad in bed and our relationship is bound to fail?

Difficult Conversations about Sex

Dear Difficult Conversations about Sex:

On the contrary – I think it means you’re very good in bed, or at least, good enough that your boyfriend isn’t unsatisfied. But it seems like you are and that’s worth talking to him about.

You say that you’ve tried offering suggestions – are these suggestions always offered in the bedroom? Sometimes that’s a mood killer and maybe he shuts you down out of embarrassment. If that is the case, try to talk to him about it at another, more neutral point in time.

You: There’s been something I’ve really wanted to discuss with you because it’s been weighing on me. Is now an OK time to talk?

If he says yes, sit down and tell him exactly what it is that is bothering you. Do you feel unsatisfied with your sex life? Is there something specific that you want to try in the bedroom? Are you concerned that he shuts down your suggestions? Or that you aren’t good in bed? Whatever it is, be open and honest about it.

There’s nothing you can do to make him want the kind of sex that you want, but he should at least be willing to have a conversation about it. After that, you’ll have to decide whether or not you want to continue in the relationship or if you are simply incompatible.

Q: My girlfriend and I are in an open relationship, but now she’s upset that I slept with someone else.

What should I do?

Open Relationship Drama

Dear Open Relationship Drama

This is a tough one – theoretically, being in an open relationship means that both parties are aware (and OK!) with extramarital (extra-relational?) affairs. But theory and reality don’t always align.

I’m not sure if the two of you failed to fully discuss what an open relationship would mean, or if your girlfriend simply thought she would be OK with it but has come to realize that she’s not, but either way, you have some difficult conversations in your future.

There isn’t anything you can do about your affair – you’ve already slept with someone else. Likewise, there isn’t anything she can do about her failure to communicate her feelings ahead of time.

So, now, sit down with her and approach the conversation with empathy.

I understand that you’re bothered by what happened. I was under the impression that you knew and were on-board with this arrangement. Am I missing something? Can you let me know more about what it is that you’re feeling?

Maybe she’s changed her mind entirely. Or maybe she wants to set more clear boundaries (i.e. – you can date other people but sex is off-limits.) Regardless, it seems likely to me that if your relationship continues, it won’t be an open one.

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Conclusion: Relationships Require Difficult Conversations

No matter how new or old your relationship is, it’s inevitable that difficult conversations will arise. The most important thing, though, is that you approach them with openness and honesty.

Do you agree with my advice? What other tips would you give for having difficult conversations with your partner?

Let me know your thoughts in the comments below. And as always, thanks for reading!


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  1. avatar

    Wow! You have the knack for handling these difficult topics! I think you are quite on point though. It’s no use taking a relationship forward if you are not comfortable communicating about things.

    1. avatar

      True – there will be a lot of other difficult conversations in the future so you have to be able to handle it well.

  2. avatar
    Seriah Sargenton says:

    I definitely agree with what you said to the second question. Maybe it’s the timing of the conversation, also the conversation on sex could make him really uncomfortable, and that’s something to consider too.

    1. avatar

      Very true – there are a lot of factors that could be at play which is why I think communicating openly is so important!

  3. avatar

    You go girl! You have such good advice. I know where I’ll need to come when i am in a jam

    1. avatar

      Awe – thanks so much! I always appreciate that

  4. avatar

    I definitely agree with all of your advice. I really enjoyed reading this and can’t wait to read more.

    1. avatar

      Aww, thank you!! That always means a lot when people tell me that!

    2. avatar
      Alicia says:

      I like reading about relationships and drama. And all I can say is shy guys are not for me. Great advice column. Like 👌

      1. avatar

        I feel like the older I get, the less I like shy guys as well.

  5. avatar

    Theory and reality not always aligning is so important to realize in day to day!

    1. avatar

      So true!

  6. avatar
    Jenny Pink says:

    I always have trouble with this, so this is a helpful post for me to come across!

  7. avatar

    What a brilliant piece of advice, Katie! On first one – I would agree with you. Probably the shy guy is not clear or not interested in moving forward with a relationship. Might be, he don’t wanna tell or share the things which probably happening in background like if he’s dating someone else or can’t see any future due to various reasons! Rest two are to the point, I would say! Talking about such an important topic wisely can really takes one to the logical closure and conclusion! Amazing post as usual, Katie!

    1. avatar

      Aww, thanks so much! I think that’s how I’d lean too – he’s either not entirely sure yet, not ready for commitment, or not wanting to tell her if he’s seeing other people.

  8. avatar

    Great advice on all of these difficult dilemmas! The ‘Are we there yet’ conversation is one that I think most couples run into at one point or another.

    1. avatar

      Totally agree – and I think how people handle it says a lot about them (and, honestly, about the relationship.)

  9. avatar

    I wouldn’t have thought that having a chat about if you’re in a relationship yet or not was less a difficult conversation, and more an awkward one. But maybe that’s just me

    1. avatar

      True – but if you can’t get a straight answer out of someone, that would make it a bit challenging!

  10. avatar

    I loved reading your answers. Thank you for sharing and creating a safe space. Many of us struggle with having difficult conversations and it’s so great to have more people talking about how to approach those topics rather than staying silent.

    1. avatar

      Awe, I loved reading this comment! It really made my day 🙂

      And yes, it’s so hard to learn how to speak up, especially when you’re young. But I’ve wasted a lot of time with the wrong men because I wanted to stay quiet and if I could give advice to my younger self, that’s what I’d say.

    2. avatar

      Wow excellent advice on difficult conversations X

  11. avatar

    This is some really good advice on these situations. This will be really helpful for others who maybe in a similar situation. Thank you for sharing.


    1. avatar

      Thanks! So glad you enjoyed!

  12. avatar
    Lou Farrell says:

    Excellent advice, the sort my younger self could have done with. Squirmy and uncomfortable is definitely a red flag. Thanks for sharing your answers 🙂

    1. avatar

      I hesitated to say it was a genuine red-flag, only because they haven’t been dating very long. But – it certainly is something I’d watch for (especially if he has that same reaction in a month or two. At that point, it’s time to shit or get off the pot.)

  13. avatar
    Mind Beauty Simplicity says:

    i’ve struggled with confrontation and tough convos and these tips and the way you explain things will really help me put things into perspective. thank you.

    1. avatar

      Good! I’m so glad you found it helpful! I have a hard time with confrontation too, but I’ve come to realize that you need to be blunt in a relationship. Otherwise, you tend to waste time and it leads to overthinking. Having to think non-stop about something or try to analyze it is REALLY tough – it’s much easier to ask questions upfront so you don’t have to struggle later on.

  14. avatar

    Really great advice on all three dilemmas and I’m sure your points will really help. It seems that the ‘shy guy’ isn’t really reserved but the reluctance to talk about where the relationship is going is probably because he doesn’t really want to say — he’s either not really into the relationship or is very into it and fears rejection, etc. The other two situations definitely need to have some really open, honest and kind conversations to help resolve what they’re experiencing. Really interesting read and fab support given here!

    1. avatar

      Ohh, interesting take on the first letter. I hadn’t considered that he was TOO into the relationship. That’s possible, but I think it’s more likely that he isn’t quite ready to say. But, maybe he doesn’t want to risk ruining what they currently have if he tells her that he’s not ready for a relationship.

Let me know your thoughts!

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