Should I reveal my conviction at job interviews and dates?

Short answer: Of course, you should be 100% honest and transparent from the start
Longer answer: You should, but it depends on the circumstances

When looking for work after release you are faced with the awkward situation that you have a massive gap in your CV that you need to explain somehow.
Lying is a very bad idea, but so is being too blasé about it and pretending it’s not a big deal.
The only solution is to acknowledge how serious a criminal record is, whilst not making it a bigger issue and obstacle to employment than it should be. The reality is that millions of people with some form of criminal record are in employment and that attitudes are more progressive than one might think.

From a legal perspective, you have to disclose an unspent conviction when asked; otherwise you commit another serious offence.  
However, that’s only the case when asked. If nobody questions the gap in your CV or asks you about your criminal record throughout the interview process, you don’t have to reveal anything from a legal point of view.

My approach

Looking for work is hard and stressful by itself and the honest truth is that having a criminal record makes it much more so.
There is the constant question of when and how to tell. You also need to explain the context of why and how you committed your offence, which can be long-winded and emotionally draining, especially if you have to do it over and over in every interview.

My approach was therefore to never mention it in first interviews, unless asked.
One reason is that it would unnecessarily overshadow everything else from the start. It wouldn’t be the right first impression – you want to give your potential employer the chance to get to know your personality, skills and strengths first.
In addition, many first interviews go nowhere and don’t want to have to repeat your story over and over, it’s just too draining.

Later interviews are a different story, especially if you are actually offered a position. Here I would say to your future employer: “I’d love to take the job, but there’s one thing I feel is important that you know.”
In most cases, you’d probably still get the job, plus you’d be so much more comfortable at work, starting on a basis of honesty and not secrecy.

At my place of work, all of my bosses know about my conviction, and I wouldn’t feel comfortable without them knowing. However, I don’t think any of my co-workers know. For me it wouldn’t matter to me if they did, and if we became closer friends I’d actually want them to know. It’s not a question of hiding anything; it’s just that it has not yet come up.

What I need to stress here is that the advice I can personally give is very limited as everyone’s circumstances are so different.
If you’ve been to prison for twenty years on a murder conviction I can’t even begin to imagine what it’s like and that of course the whole process described above will be a lot harder than it was for me. But it would fundamentally still be the same, just a lot more difficult.

The dating world

Let’s be so honest to admit that having been to prison doesn’t instantly make you the catch of the century. You therefore don’t want to blurt it out as the very first thing you say to every one you meet, but at the same time you don’t want to keep it a secret for too long either.

What I found is that the more I liked someone, and the more I wanted to see them again, the more I felt the need to tell them about it. How could you not talk about something so significant in your life, something that was so formative and has become part of your identity? Especially with someone you like and want to meet again.

As always, context matters, and there are no hard and fast rules. I’m probably not doing myself a favour by being too honest too soon, but everyone has to do what feels right to them.

Especially with something so subjective and random as dating. The truth is that nobody has the answers and if you’d ask anyone, their answers would reveal more about their views and personalities than help you.

Conclusion

What I found, both when looking for work as talking about my crime on dates, is that people are a lot more understanding than you might think.
Not once have I received a gasp of shock and appalment, not once have I received a rejection solely relating to my conviction.
Yes, I didn’t get all the jobs and dates I wanted, but most of time that had less to do with my time in prison than other factors.

It’s important to be honest and realistic to oneself

What I find to be the most important thing is to be honest to ourselves about the truth of what we have done, who we were then and who we are now.
That’s not an easy thing to do. But not facing up to reality and trying to mitigate our own culpability prevents us from moving forward.

As much as everyone makes mistakes and everyone deserves a second chance, we have to accept that people have the right to say no to us.
Employers have the right to not hire us because of our history and dates have a right to say, “well, at this stage in my life I just don’t know if I want to be with someone who has been to prison.”
That’s hard but makes it so much more rewarding when people say yes.