When do I talk about my criminal record?

Hello Meredith and the LL community,

My dilemma involves dating with a criminal record/past. Please be honest but not cruel. Here it goes:

I am post-divorce plus a few long-term relationships. A handful of years ago during a particularly difficult time, I succumbed to all the life pressures that surrounded me and committed a series of "white collar" illegal acts within a short time period of time (less than a few months). I somehow snapped back into reality and crawled out of my deep clinical depression just enough to stop. Prior to all of this, I was somewhat the average Jill. I say "somewhat" because there is a history of child abuse, an abusive marriage, other skewed relationships, and the related pit-falls of those.

Not surprisingly, due to my history, there has been long-standing depression, which I survived without serious long-term consequences. Unfortunately, during the time period in question, I was not able to rally myself and committed these acts as a serious cry for help. As I said, I somehow snapped back into reality, felt extreme remorse, stopped the acts and continued with my life with a promise to myself that when life permitted, I would concentrate on getting the help I desperately needed. Fast forward a number of months from that realization and future self-help promise, the authorities became involved and the legal process began. While they conducted their investigation, I confessed and cooperated. I didn't even try to justify my actions or defend myself against the charges, aside from working out a plea.

Although I am sure it will happen, I am not looking to be flogged. I literally and psychologically served the time for my criminal acts. I think about this every day.

I am female, educated, and have a respectable career. In the years that have passed, I did get the help I desperately needed and continue with that support. I have cleaned up other areas of my life, terminated toxic relationships, and have had a lot of "me time" and I am now in a really good place. What I did during those months years ago is not who I am.

I will be beginning the process of putting myself out there in the dating world in hopes of eventually entering a serious, committed relationship. At what point do I divulge the above? Please, I am not asking if I should, I am asking when. I obviously don't want to be judged for one aspect of the sum of me (albeit a significant one), but I also believe in 100% honesty and I don't want to put anyone in the difficult position of feeling duped because I took too long to provide them with critical data for them to consider. I know that every situation is different and I will have to learn the balance once I actually start the process. I was hoping you could give me some guidelines to keep in mind and prepare for in advance.

As an aside, would you consider me un-datable? It won't deter me from trying, but I am curious enough to ask. I really am a good person and would be considered such by all that know me ... BUT I also know I carry a huge deal breaker.

– Somewhat Average Jill

I don't think you're un-datable, SAJ. You seem self-aware and positive. You've dealt with whatever it is that you did. You're being responsible about your depression. You have a good job. You're smart. One might even say that you're a catch.

Of course, not everyone is going to feel that way about you. I can't lie about what I might do if a person on a date told me they served time for a white-collar crime and "learned their lesson." It's true that the disclosure might cause me to run for the nearest exit. But -- I can't say that for sure. Dating and love is all about vibes. Sometimes we get bad vibes from people who have clean records. Other times we get awesome vibes from people who've made big mistakes. Hopefully, someone will get a great vibe from you.

My dating advice is to get yourself into a good circle of friends, a pack of nice people who can really get to know you and vouch for your character. It might be difficult to date online with your past -- because online dating involves quick judgments. But if you meet people through friends, those potential mates will know that you're surrounded by good folks who see you as a trustworthy person. They'll see you in context. Context is really, really important. You'll be able to talk about your mistakes whenever it feels natural, whenever your past comes up and it's time to share. Probably within a few dates. Before anything gets serious but after you've shared some of the good stuff.

Readers? Would you forgive a criminal record? When should she tell dates about her past? Agree with my advice about how she should date? Discuss.

– Meredith