Dear Anna,

My boyfriend and I have been together for a little over two years. We live together with his two boys and my son. About a year ago, I found out he had been cheating on me. He was messaging women on dating apps and Craigslist, and he was also talking to and possibly hooking up with trans women. I found emails and texts with several people.

I didn’t know he was attracted to trans women, and when I asked him to be honest with me about his desires, he got very upset and shut down. He even said it “wasn’t really cheating” because they “aren’t really women,” which hurt and confused me.

He insists I’m the one he wants to be with. Our relationship has been “OK” since then, but I still feel insecure. Sometimes I wonder if he’s really attracted to me. Our sex life is fine, but he rarely goes down on me (which I do for him all the time), and he prefers anal and other positions where he doesn’t really look at me.

Recently I went through his phone again and found emails from a dating app. There are also still a few Craigslist emails, and he’s been looking at trans dating sites. He says he isn’t acting on it — just looking at pictures.

I don’t know how to approach this anymore. I love him and our family. I don’t want to lose him. He wants me to trust him, and I want to trust him. He hasn’t physically cheated again since last year (as far as I know), but the insecurity is still there. I’m scared I’m pushing him away, and I don’t want to lose him. What do I do? — Please Help

Dear PH,

Let’s separate something immediately: This is not about trans women.

Trans women are women. They are not a loophole or a fetish or a technicality. And above all else, they are not responsible for your boyfriend’s choices.

Your boyfriend cheated on you. Hard stop.

And when confronted, instead of taking accountability, he minimized it by claiming it “wasn’t really cheating.” That’s manipulation. And deflection. It also happens to be extremely dehumanizing and objectively s—ty toward trans women, which is its own red flag — but also, he rewrote reality to avoid taking responsibility.

So to sum up, he’s cheating, lying, minimizing, deflecting and using trans women as a shield for his behavior.

Now let’s zoom out.

A year ago, you discovered he was actively seeking other people on apps and Craigslist. Now, a year later, he is still hovering around dating apps and browsing hookup sites. Maybe he hasn’t “physically cheated” again. But he is absolutely still investing sexual energy outside your relationship.

Trust isn’t rebuilt by reactivating dating apps “just for the pictures.” (I mean, really!)

Trust is built by transparency, accountability and changed behavior.

Right now, what I see is this:

—You adjusting your sexual preferences to please him

—You performing oral sex regularly while your needs are rarely prioritized

—You worrying that you’re pushing him away

—Him browsing dating sites

You are bending yourself into so many uncomfortable shapes to keep him.

And he’s keeping his options open.

That imbalance is … not leading anywhere good.

Your insecurity isn’t coming from nowhere. It’s coming from inconsistency. From secrecy. From the fact that you had to find things instead of being told. From the fact that when you asked about his desires, he shut down instead of having an adult conversation.

You’re worried about losing him. But I want you to gently consider: What exactly are you trying so hard not to lose?

I understand not wanting to blow up your blended family. I understand the security, the shared bills, the practical stability he likely provides you and your son. That’s real. Those are not small things.

But here’s a hard question: Is this the relationship you want your child to grow up thinking is normal? Because kids don’t learn from what we say. They learn from what we live.

And what I see is a man who cheats, minimizes it, continues browsing hookup platforms, rarely prioritizes your pleasure and tells you to “just trust him.”

Love and family stability are powerful forces. I understand why you want this to work. But wanting to trust someone does not create trust. Their behavior does.

You’re not pushing him away by wanting honesty and exclusivity, if that’s what you agreed on. Those are baseline relationship requirements unless otherwise negotiated.

If he has desires outside your relationship — whether that’s curiosity about trans women, other partners or non-monogamy — that conversation needs to happen explicitly. And you get to decide whether that dynamic works for you. But what you have right now isn’t ethical non-monogamy. It’s unilateral wandering.

The question isn’t how to stop pushing him away.

The question is: What would it take for you to feel secure here? And is he actually willing to do those things?

If he isn’t, are you OK with a lifetime of shrinking, contorting yourself, performing, ignoring evidence and hoping he stops looking?

You deserve a relationship where you don’t have to compete with browser history.

And you absolutely deserve one where your partner takes responsibility for his choices — without blaming entire groups of women in the process.

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