Dear Ken… Should I let her go?

I’ve added a page where you can submit advice letters, and we’ve already received a few! Dat is so crazy. Feel free to send in your questions on the ‘Dear Ken’ page. Let’s see how we can support each other. Sarai wrote in and gave permission to use her name—I'll leave comments on just in case you'd like to add your thoughts two cents.

Letter

Subject: Should I let her go?

Message: I was talking about what I’m writing you for with my sister she told me about your blog and told me to write in here I just wanted to let you know so you know you have men who read and enjoy this. Ite so my name Mak and I’m 29 I live in Chicago. I started talking to someone in the summer, before that I hadn’t dated anyone since early 2023 because I didn’t like how I was showing up for the women in my life so I took a step back, got in therapy, put a lot of work into my career, and health. I’m now in a comfortable spot I’m an engineer and feel like things are going well to the point that even my therapist brought up dating. So I get back on the apps and started meeting people. I met this girl and we went on a date and it was decent we started spending more time together and feelings are growing. She’s decent as hell and I can see myself locking it down. We started getting more serious before the holidays and met each other families. She had relationships in the past where the niggas cheated on her or did goofy shit and I’m paying for that. She goes through my phone which I don’t really care too much about it’s the fact that she’s going through it looking for things that aren’t there. I deleted the apps probably in september when we started going out more so of course they aren’t on my phone she went to the App Store and seen they weee previously on my phone and had an attitude I was so confused because …. We met on the apps so you know they used to be on my phone??? I went to DePaul and have a lot of friends from there some who are girls and strictly platonic and she’ll have problems when they are around or reach out to me, I’m not really cool with getting rid of my college friendships since nothing about them are inappropriate. My issue is I’ve spent a lot of time and money in therapy and growing that sometimes this feels like even though I really like this girl she may not be a healthy choice for me. How do I tell her she should get in therapy and I’m serious about it without sounding controlling or brewfurd? It ain’t fair what her past did to her she wasn’t supposed to have people to treat her like that but I don’t feel like I should be punished for things they did. And it can be triggering because I had experiences where I wasn’t the best man for a woman and have cheated or played games in the past I can sometimes feel guilty and want to fix everything that I didn’t break I guess to clear my conscience. I want to see this work because she has so many qualities I like and I have never felt the way I feel about any woman with her I don’t want us to be unhealthy for each other. Thank you

Response

Hey Mack,

Ahhh, the blog has reached the men. Welcome! You’re doing a lot of important work, both in reflecting on your own past and trying to figure out how to build something healthy with her. I really respect that you're considering how your past guilt impacts your current relationship, and you’re asking the right questions. Guilt is a tricky thing, especially when it comes from past wrongdoings like cheating or playing games. You might feel like you owe it to your partner to make up for past mistakes, but you can’t fix everything you didn’t break. Guilt can sometimes lead to overcompensating, being overly cautious, or constantly feeling like you're walking on eggshells to "make things right." And while that’s well-intentioned, it’s not the healthiest way to go about it, and it can sometimes cause more harm than good.

Now, when it comes to your partner’s past and how her trauma might be showing up in your relationship, I want to dive a bit deeper. It sounds like she’s had some significant hurt from past relationships, especially from infidelity and emotional betrayal. And what you’re noticing now—the hypervigilance, the checking your phone, the insecurity around your friendships—is very much a symptom of how trauma, especially from cheating, can affect someone on a deep level.

Here’s some psychoeducation on why this happens: Infidelity, or any betrayal in a relationship, can have effects that are remarkably similar to PTSD. When someone experiences cheating, their trust is broken in a way that goes beyond just a “normal” betrayal. It affects the brain’s stress responses, much like trauma does, and triggers something called hypervigilance. This is when someone is constantly on edge, anticipating danger or harm—even when there’s no immediate threat. They may become extra sensitive to things that might seem harmless to others, like your platonic friendships or past dating apps on your phone. Their brain is constantly scanning for “evidence” that the betrayal might happen again, so they react strongly even if they’re not consciously aware of why.

That hypervigilance can show up as intrusive thoughts, anxiety, and a general sense of being unsafe in relationships. It's like their nervous system is always in "fight or flight" mode, which is exhausting for both the person carrying the trauma and the partner. So when you see her going through your phone, or becoming upset about things that seem minor to you, it’s not necessarily about you—it’s about the fear and insecurity that come from unresolved pain in her past.

That said, before jumping into a serious relationship, especially when someone has past trauma, both partners need to do the work to process that baggage. If you were to continue without addressing these unresolved issues, it’s like trying to drive a car with the parking brake on. It’s not going to go anywhere smoothly. Your baggage and hers needs to be dealt with in a way that doesn’t derail the relationship, and therapy is a great way to start that process.

I’m not saying call things off, no one is free from baggage—not you, not her, not me, not anyone. But with the right support and effort, we can manage it and not let it control us. It’s like we’re all carrying a backpack full of emotional stuff—some people’s backpacks are heavier than others. What’s important is how we deal with that weight. You can’t just throw your backpack on the floor and ignore it, but with the right tools (therapy, support, self-reflection), you can put that baggage in the car and still make it to your destination—together. You’re not expected to carry the whole thing for her, but you can help her unpack it if she’s willing to work on it.

So when you talk to her about therapy, it’s important to approach the conversation gently, using "I" statements and soft start-ups to keep things calm and open. You can say something like, “I’ve been doing a lot of thinking about how we can make this work, and I really want to be a good partner to you. I know your past relationships have hurt you, and I respect how hard that must be to carry. I also want to make sure we’re both in a place where we can build something healthy, so I think it could be helpful for both of us to continue working on our own healing. I’ve been in therapy to grow and be the best version of myself, and I really believe it’s something that could support you too, in processing everything that’s come up for you.”

This way, you’re showing empathy while also making it clear that you believe therapy could be a step forward for both of you, not just her. You’re coming from a place of care, but also from a place of self-respect. You’re not taking on her emotional load, but you’re offering support in a way that doesn’t feel like you’re trying to control her.

The most important thing is that you're giving her the space to do the work that’s necessary, without feeling like it’s being forced on her. You can even use humor to lighten the mood. A little humor goes a long way in these tough conversations, but the point still stands: you want to be moving forward together, not carrying unnecessary emotional weight that holds you both back.

Ultimately, Mack, it’s about doing the work—not just for her, but for you too. If you’re still carrying guilt from past relationships, it’s important to process that, so it doesn’t cloud your present. You can’t fix what you’ve done in the past, but you can be a better version of yourself today. And that’s what matters.

Relationships are hard, but they don’t have to be painful or toxic. With the right work and communication, you can build something strong. But if that work isn’t happening—on both sides—it’s time to reconsider whether it’s the right relationship for you.

You’ve got this, Mack. Keep doing the work and keep being real with yourself. That’s how you build something that lasts.

I’m rooting for you!
Ken