Dear Dating Bitch: How to Handle Difficult Conversations with Your Partner

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 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

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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.

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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!

xx
Katie

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