We all carry a certain amount of relationship baggage with us. It’s normal and even healthy to an extent. And most of us have learned how to deal with our own baggage. But what about someone else’s? How do you deal with a new partner’s emotional baggage?

That’s what one reader is currently dealing with. Today, I’m answering that question along with a few other interesting relationship queries.

But first, if you’re new to the blog blog, Dear Dating Bitch is my modern day advice column. If you’re in need of some advice, go ahead and submit your questions here. And don’t worry – it’s always anonymous.

Now then, let’s get today’s letters, shall we?

Related Read: 5 Tips for How To Let Go of the Past
Help - A guy I'm seeing has a lot of relationship baggage and I don't know how to deal with it.
*Note: Questions may be edited for length/clarity

Dear Dating B: Advice on Relationship Baggage

Q: I’ve recently started seeing a new guy. I’m really into him, but I’m struggling with a few things. Namely, the timing of it all. We live in a high rent area and because of that, he was living with his ex for a few months after their breakup. He just moved out three weeks ago. They broke up after she texted him one day saying she’d cheated on him with a co-worker. Also, this happened after she withheld sex for nearly two years.

He’s incredibly sweet and I like him a lot. I really want this to work, but I also know I need to tread carefully here due to his baggage. I don’t want to push him too far, too fast and make him feel smothered or overwhelmed. At the same time, I don’t want to give him so much space to the point where he thinks I’m not interested. How can I balance this and help build his confidence back up?

Even if things don’t work out between us, no one deserves that kind of treatment.  

Relationship Baggage Check

Dear Relationship Baggage:

You’re right that it’s not great timing for this relationship.

Your new beau is going through an extremely difficult breakup. He was in a serious, long-term relationship. And the breakup came after his ex-girlfriend not only cheated on him, but told him in a seemingly cruel and callous manner. On top of that, they went for two years without physical affection. That’s a lot to deal with.

From your letter, I gather that they broke up 3-4 months ago. Honestly, that’s not very long. Especially when you consider the fact that they continued living together until recently. They might’ve been broken up, but I doubt he was doing a lot of emotional healing while his ex was sharing the same space. I’m not sure when the two of you started dating, but it takes time to get over the kind of intense heartbreak he’s experiencing. Much more time than it seems he’s had.

That said, I think you should take a step back from this relationship. I know that’s not what you want to hear, but I also know that you can’t fix someone else’s broken heart. And trying to is a surefire way to hurt yourself in the process.

You mention that you’re worried about pushing him too far or coming on too strong. But, based on his specific relationship baggage, I’m not sure why you’d be worried about that. Do you have a reason to think that he’s emotionally avoidant or closed off? Or are you just afraid that he’s not ready for something serious. I’m pretty sure I know the answer and I’d be willing to bet you do too.

Related Read: Dear Dating Bitch: How to Deal with an Ex

Again, I wish I knew when you started dating, but I’d guess it’s been about a month or two at most. Right now, you should be feeling the normal dating butterflies, not anxiety over just how much space to give him to strike the right balance. It’s not your job to make him trust women again. You’re not responsible for building his confidence back up, either. That’s a lot of pressure for a new relationship.

So, my best advice is not to get into a relationship with him at this stage. Let him work through his issues first. Since you have strong feelings for him, you can end things now while still leaving the door open for the future.

“Jack, I really like you and I want to see where things go with us, but I don’t think now is the right time for that. I know you’re dealing with a lot. What you went through is heartbreaking and no one deserves that kind of treatment. But I think you need more time to heal before this goes any further.”

Q: A close friend of mine still has feelings for her ex, who also told her he still loved her, despite the fact he’s in a relationship. This seems like a red flag. Now, she’s told me that she is just going to stay friends with him. How do I tell her that’s a bad idea?

Concerned Friend

Dear Concerned Friend:

It could definitely be a red flag. I highly doubt that the new girlfriend would like this at all; at the very least, it could be seen as emotional infidelity. Your friend’s ex could also be genuine in his ongoing love for her and/or desire for friendship. Both of those things can be true at the same time.

No matter what this ex’s intentions are, I agree with you: being in his life seems like a bad idea. So, tell her that.

“Friend, I care about you a lot and I don’t want to see X hurt you again. I really don’t think it’s a good idea for you to stay in his life.”

But, if she chooses to pursue it anyway, that’s her choice to make. Be a supportive friend. That means, not judging her for making a bad decision, not saying “I told you so,” when that decision ends poorly, and being there for her when she needs you.

Related Read: 5 Tips for Moving on From a Bestie Breakup

Q: Should you be concerned if your boyfriend keeps his ex’s underwear?

Victor’s Secret

Dear Victor’s Secret:

Yes. I can’t think of any possible reason that wouldn’t be concerning, creepy, or both.

☆ ☆ ☆


Sometimes, the relationship baggage we’re dealing with isn’t our own. And while it’s noble to want to help someone else carry their heavy load, it’s not always possible. What’s more, it’s not always helpful.

What do you think of my advice this week? Let me know in the comments below!

As always, thanks for reading. If you’ve got questions of your own, make sure to send them to me here!


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  1. avatar
    Jodie | That Happy Reader says:

    I love your responses to each of these situations and think you’re “spot on”! Thanks for sharing these posts!

    1. avatar

      Awe, thanks a bunch. That always means so much to me.

  2. avatar
    According to Chren says:

    That guy sounds like a red flag. He might do the same thing to your friend if they got back together. We’d be concerned that he only wants what he can’t have.

    1. avatar

      I completely agree – if it seems sketchy, it probably is.

  3. avatar
    Amazing Baby says:

    OMG!!! I love this advice column! I wholeheartedly agree with the advice you gave ‘concerned friend’. Don’t hold on to hope that the ex will come back to your friend; the ex has already made his choice, and it’s not your friend. It’s a hard pill to swallow. She’ll appreciate it when someone chooses HER (and only HER)!.

    Crystal | http://www.amazingbaby.app

    1. avatar

      Thanks so much! Glad you’ve enjoyed!

  4. avatar

    Reading this it all seems like really sound advice; I hope all those that asked find some kind of resolution and way to move forward!

    1. avatar

      Thanks! I always love getting advice column questions.

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