I’m 38 and have never had penetrative sex. My attitude oscillates between deep shame and embarrassment (that shame is a part of the reason I dated so little in past), and comfortable acceptance that we all have our own journey, and that mine looking a little different isn’t such a big deal.

I feel like I’m really finally ready to experience this with someone. I think I’m in the best place I’ve ever been emotionally and mentally about myself and my desire for romance.

My question is – do I disclose this?

There was one guy last year I had been dating for a month and really was into. When I told him, I explained some of my background (religious upbringing, difficulty with vulnerability when I was younger), and explained how I am not expecting anything if we choose to do this, I know penetrative sex isn’t “special” or means anything. I just felt like it was something I should disclose.

The guy freaked out and completely shut down, refused to talk to me at all and wanted nothing to do with me. My friend say I should have told him in person and not over text, but I feel like I can explain myself better and communicate better via text.

Obviously I was crushed, but I was also SO proud of myself. It felt so good to be vulnerable and share my whole self. I knew at the end of the day it was him with the issue if that was so terrifying for him. He wasn’t a safe person emotionally to be with so I feel I really did dodge a bullet, despite being hurt.

So that takes us to present day. Should I continue to disclose my [lack of] history to partners?

I don’t plan on disclosing until 4/5th date, or when getting to a point where sex would be the next step.

I was thinking I will take an informal survey and tell the next 4 people I date (assuming we get to the 4th or 5th date which hasn’t happened yet w anyone). If the next 4 people all freak out, I will stop telling people.

I have friends who say I shouldn’t tell guys because they’ll get freaked out and weird.

But it feels icky to me to try to have sex with someone without disclosing my status to them. Idk it just doesn’t feel right and feels like a backwards step in my work towards being more vulnerable.

On the other hand… it would be nice to check this off my bucket list and not have it hanging over me all the time.

Idk how long it will take me to find someone I am into who can handle this info.


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