On Exes and Envy – How to Handle Jealousy the Mature Way

Welcome back to another edition of Dear Dating Bitch! If you didn’t know, this is one of my favorite types of blog posts to write, so I’m always happy to get questions from readers.

Today, I have a couple of questions, all of which are about exes and how to handle jealousy in a relationship.

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

*Note: questions may have been edited for length/clarity.

Dear Dating Bitch - I don't want my boyfriend to be friends with his ex.

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Q: Am I a bad girlfriend for not wanting my boyfriend to be friends with his ex?

How to handle jealousy

Dear How to Handle Jealousy:

This is a straightforward question, but there are a lot of layers to it, so, I’ll start with the most obvious and work my way to the center of the onion, so to speak.

No, you’re not a bad girlfriend for not wanting your boyfriend to be friends with an ex. Experiencing jealousy in a relationship does not automatically make you a bad partner. BUT, how you handle jealousy might.

Put more simply, you aren’t doing anything inherently wrong by feeling the way that you feel. But, usually when people ask if they’re a bad A because they’re feeling B, there’s a missing C from the equation. And that C would be the action.

So, how are you acting?

Are you looking through your partners’ phone/email/social media in attempt to monitor who he’s talking to? Or are you being passive aggressive when he mentions grabbing a quick coffee with his ex? Do you him of cheating on you anytime he talks to her?

Without more information here, I would say that you need to do two things:

First, figure out why you don’t want your boyfriend to be friends with his ex. Do you sense that he’s being unfaithful? Do you feel like he sees or talks to her too often for your liking? Did you have a bad experience in your own past that might be causing some bias? Or are you just generally unsure/uncomfortable with the idea of him remaining friends with someone he’s seen naked before?

None of those answers are inherently wrong, but it’ll lead you to part two: talk to your partner.

Explain how you’re feeling and why you’re feeling that way. I think it’ll be important that you not try and control what your partner does after that – you can tell him that you feel uneasy but that doesn’t mean you can tell him who he can or can’t be friends with.

Instead, focus on how you feel, not how you want him to react. Sometimes, the solution is just that you need to feel heard and understood.

Q: Is liking pictures of your ex girlfriend cheating?

Still Facebook Friends

Dear Facebook Friends:

Your girlfriend didn’t also happen to write in, did she?

No, I don’t think that liking pictures of your ex is cheating – but I have to wonder what kind of pictures you’re liking that would make you feel guilty. Are they general Facebook update pictures, or are they the kind of Instagram pictures that could easily pass for those found on Only Fans?

But, if you do feel like you’re doing something wrong, you should probably think about why you feel that way and why you’re continuing to like photos if all it does is make you feel bad.

Q: My ex wants to meet up to exchange our things. It’s been a month since the breakup – what should I do?

Post-Breakup Anxiety

Dear Post-Breakup Anxiety:

As much as you might want to burn all of his stuff and never answer his exchange request, you can’t in good conscience not return someone else’s things, no matter how much of an asshole they might be. And, that sucks, I know! (I’ve got my own story on that… but I’ll save it for another day.)

But, you CAN decide not to exchange things in the way he wants to. Meaning, you don’t have to meet up with him. You don’t even have to see him face-to-face if you don’t want to.

If that’s what you’re worried about, you have options. You can either A) tell him that you will put his things outside on your front porch on X date/time and let him pick them up without any interaction, B) return his things by leaving them outside his place, again, leaving no need for actual interaction, or C) ask a mutual friend to facilitate the exchange and act as middleman.

Be warned – he might balk at this. He might give you a hard time about refusing to actually see him – I’ve been on that side of things too, so I get it, but you can simply tell him that you’re not ready/comfortable with meeting up and let him know (firmly, but kindly) that if he wants his stuff back, that’s how you’re willing to make the exchange.

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Conclusion: Handle Jealousy and Exes with Dignity

That’s it for this week friends! As much as you might want to destroy your exes favorite t-shirt or force your partner to expunge their ex from their memory, you have to handle jealousy and ex-boyfriends with dignity and maturity.

But, of course, I want to hear what you all think.

Do you feel comfortable with your partner being friends with an ex? How do you handle jealousy in relationships? How do you handle having to make the big exchange after a breakup? Let me know in the comments below.

As always, thanks so much for reading!


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  1. avatar
    Michelle Gast says:

    I’m very jealous. I can’t handle him being friends with his ex, and we’ve been married 18 years!

    1. avatar

      Wow, that’s so interesting! But everyone has their own standards in relationships

  2. avatar

    As always wonderful post, Katie! Brilliantly thought off and very nicely analyzed, I must say! I really feel that when possessiveness crosses the path it becomes jealousy, though it varies individually but that’s what I feel about it!

    1. avatar

      Aww, thank you so much! I always really look forward to your comments – they really brighten my day 🙂

      1. avatar

        It’s always a pleasure reading your contents! ?

  3. avatar

    These are some interesting questions. I really enjoyed reading these questions and the advice you have given. Thank you for sharing.


    1. avatar

      Thank you! So glad you enjoyed

  4. avatar

    I always enjoy reading these posts! I’m friends with almost all my exes and my exes have exes they’re still friends with. I love the advice you give and think it’s always best to put everything out in the air so everyone knows how they’re feeling.

    1. avatar

      I agree – I have some exes that I’m still friends with, but when I read this question I wondered if there was more to the story that wasn’t being shared. Either way, having things out in the open and communicating openly is always a good way of dealing with insecurity in relationships.

  5. avatar

    I really liked your two parter response to that first question! When I first started dating my fiancé his ex wanted to be friends with him and he let me know she’d asked to meet up. But then she started messaging him all the time and asked if they could go for dinner instead. I didn’t feel comfortable with that so I told him how I felt about how often she’d been messaging and changing a casual coffee meet to a dinner date and he decided not to go. I never told him he couldn’t, but I was honest about my feelings and I’m glad we handled it that way.

    1. avatar

      Love this story! It shows so much respect from your fiancé that he would set boundaries based off your needs. He sounds like a great guy!

      1. avatar

        Thank you John 🙂

        Seems like something you would say, too ?

      2. avatar

        He is a gooden.

    2. avatar

      Yeah, I think that situation shows that she was clearly trying to overstep some boundaries. And I think that really shows how you don’t need to tell someone what to do, you just need to express your feelings and let them react to it. Everyone has different needs and wants in a relationship, so I’m glad you two were able to find what made you both feel comfortable.

      1. avatar

        Absolutely. The fact that she then started sending him messages saying it’s a shame I’m so jealous and controlling or they could have some fun kinda sealed the deal.

        1. avatar

          Ooof. Yeah, that wording definitely says something. Almost seems like she was trying to guilt/shame him into meeting up with her? Sketch, very very sketch. I say you were right to feel worried in the first place.

  6. avatar

    I very much enjoyed the methodical and pragmatic approach that you take to helping people with their questions and I thought it was brought to life through your writing too. I found myself nodding my head at your advice and thought you answered the questions well.

    1. avatar

      Thank you for that! Always makes me happy to hear

  7. avatar

    Even though I’ve been married many years, I still appreciate reading this type of post. Thanks for sharing.

    1. avatar

      Awe, thank you! I’m so glad to hear that.

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