My boyfriend and I have been together for just under a year, and we’re 36 and 39.
He’s a great person, and things are going really well, I think this is endgame. But I’m struggling to let go of his past. In his early 30s, he had a reputation for being a bit of a creep—pestering women and not knowing when to stop, though nothing harmful or dangerous. Honestly, if I’d known him back then, I wouldn’t have given him a chance, his behaviour was pretty embarrassing by how it sounds.
Since then, he’s had a wake-up call and changed a lot from what I can tell. He’s socially awkward and likely on the ASD spectrum. He’s only ever treated me with kindness and respect. My issue isn’t with who he is now, but when his past comes up, I feel embarrassed and uncomfortable. I’m also worried about friends finding out and judging him.
I want to move past it and focus on the person they are today without letting it overshadow my relationship but I dont know how. I don’t like thinking badly of my boyfriend, but it’s not even him I’m thinking badly of but some past version! I also know that I could tell him things about my past that would put him off me. I don’t think I’m better than him.
Let’s start with a deep breath. It sounds like you’ve got a lot spinning around in your head—and honestly, it’s valid. When someone we love has a past that’s hard to reconcile with who they are today, it can trigger all kinds of emotions: embarrassment, confusion, even a little fear. But let me say this loud and clear: who your boyfriend was is not the same as who your boyfriend is.
We all carry a past. You. Me. Him. Some of it’s messy, some of it’s just downright cringeworthy, and some of it feels like an entirely different person lived it. What matters most isn’t where we’ve been but where we’re headed. And from what you’ve said, this guy has done the work. He’s not the awkward, boundary-crossing guy he used to be. He had his wake-up call and chose to change. That’s huge. A lot of people never even get there.
So what’s happening here? It sounds like two things:
- You’re feeling embarrassed by his past because you’re worried others will judge him—and, by extension, you.
- You’re struggling to trust that his past self is truly in the past.
Let’s tackle the first one. This fear of judgment is less about your boyfriend and more about how you feel about being associated with someone who used to act in ways you don’t agree with. That’s okay. It’s normal to feel protective of your relationship and the image it presents to the world. But here’s the truth: other people don’t get to decide if your relationship is good or bad, healthy or unhealthy. You do. And if he’s treating you with kindness, respect, and love, then let them think what they want. Their opinions don’t have to be your problem.
Now, on to the second one: trusting that his past is truly behind him. You said something really important: “He’s only ever treated me with kindness and respect.” If he’s showing up for you today as a different person than he was back then, let that be what you judge him on. Not who he used to be, but who he’s choosing to be now. That’s what integrity looks like—owning your mistakes, learning from them, and walking a new path.
Here’s something to keep in mind: you’ve got a past too. And you know what? If he’s the guy you think he is, he’d listen to your stories, maybe wince a little, and then say, “That’s not who you are now. You’re my person.” So offer him the same grace you’d want for yourself.
Lastly, if these feelings keep popping up, talk to him about it. Not in an accusatory way, but in a vulnerable, open-hearted way. Something like, “I know you’ve worked hard to grow from who you were, and I love who you are today. But sometimes I feel stuck in my own thoughts about your past, and I want to let that go. Can we talk about it?”
At the end of the day, relationships are about grace, growth, and commitment to the people we are becoming—not the people we once were. So if he’s showing you every day that he’s the guy who deserves your trust, lean into that. The past doesn’t define your relationship—the choices you both make today do.