I was transferring data between laptops and found many simping emails and text messages with an SB I was gaga over a couple of years ago (you may recall my posts about it). Reading them invoked a deep sense of shame and humiliation.

It also invoked a sense of panic because simping led me to discard all common sense opsec precautions. The messages were sent from my personal gmail, personal mobile, included personal photos, documents, bank statement screenshots, credit card screenshots etc.. Plausible deniability is out of the question.

I want to delete the emails and text messages because reading them is embarrassing and I don't want my next of kin to lose respect for me in the event I pass away (they are the legacy contact on my gmail).  

A little voice in my head says I should hang on to the emails and texts in case SB ever tries to blackmail me. The end of our relationship didn't follow Herbcat's "never burn bridges" maxim. When I told her I was cutting her off financially, she asked me how my ex-wife and my kids would feel if they knew about our relationship. I interpreted that as a threat and paid her bills for a month afterwards.

Thoughts? Do you follow a comms retention policy e.g. retain records for 7 years?

DISCLAIMER: This is not legal advice. I am NOT a lawyer in any way. I don't play on TV and the only legal training I have is from annual corporate compliance and regulation courses which definitely do not include "Sugar Law."

 
Let's start at the end: Should you keep these docs as a hedge against blackmail?  

 
Having said that, it seems like this needs a nuanced approach. My thought is to keep anything that may incriminate her; threats, demands, questions/convos about contacting your ex, kids, friends, etc. If she ever reappears with renewed threats, go to the police.  If you are going to be outed anyway, better to own the message with your family and bury your embarrassment when you ask LE to start a felony investigation. You won't be the first guy they've seen get blackmailed by an estranged woman.  Everything else; burn it (ok, delete it).  However, know that deleting a file, email, pic etc. off your device (phone, laptop, etc.) will not delete it from any internet channels that that data travelled. Your sent and received emails and attachments are likely recoverable from your email service  - IF - anyone has a legit reason to look for them.  Fortunately, the only legit reasons are if you specifically ask, or if LE obtains a search warrant signed by a judge.  

 
Next: This lookback at your past experiences makes for a good lesson on living in the Sugar Bowl.  I've heard people who are not in this space refer to any SD as a simp.  That's just not true.  But there is a learning curve that can pass dangerously close to simping. You have completed that journey and arrived in a good place. We can all learn from your experience. So thanks for sharing this story.  

 
Life is good

 
The Cat

Is to keep everything.  If someone reaches out to me years later I want to remember the conversation.  I have several blocked numbers.  Just in case I see a pic I recognize or a name I can search through old texts.

You could print the emails you want to save and then delete from your email account.   Or you can export your emails and keep them locally on your computer or a flash drive.

Since you mentioned gmail, "it is possible to download emails from Gmail, either individually or in bulk. Individual emails can be saved as .eml files via the "Download message" option in the three-dot menu. For backing up entire accounts, labels, or large volumes of data, users can use Google Takeout to export mailbox data into a .mbox file. "  For more details just search on how to download email from gmail.