I divorced about 10 years ago when my son was 3. I was a single mother with no help from my son's father in terms of reliability to give me time off. To make matters more complicated, I was struggling with depression and my son was displaying behavior that was difficult to handle for me, as well as family members who may have been able to sit for him. I really never trusted babysitters due to his behavior and if I did, I used that time for stress-free grocery shopping.
It's 10 years later and I have not been on a date (or anything that can be considered "date-like" like hook-ups, etc). I'm not asking about how to "get out there" because I know how, I just haven't done it. When I do finally meet someone and start a relationship, do I tell him it's been 10 years? If so, when? Will he think I'm damaged goods or that something is wrong with me? I'd hate to go into the story about how my life has been over the years.
I should add that after the depression, I was diagnosed with bipolar, which has been managed pretty well over the years. I've also been told that I have symptoms that might turn into physical health problems down the road. I'd also like to ask: When do you disclose any kind of mental/physical health situation?
– The Reluctant Celibate
First and second dates should just cover the basics. You should be asking yourself, "Do we have fun? Is he asking nice questions? Do we have similar interests? Do I want to see him again? How well am I getting to know him?"
If he is asking good questions, this stuff will come up naturally over time (guessing between Date 4 and 7). Let it all come up in context rather than making some big, scary "I have to tell you something" disclosure. There's an understandable reason why you took a 10-year hiatus from dating, and it sounds like you've been incredibly responsible about treating the bipolar. When you do talk about these issues, you don't have to be ashamed. Own your past. And remember to talk about the good/fun stuff you've done over the years, because I'm sure it hasn't been all negative.
Also: Don't get so wrapped up in yourself that you forget about your date. You should assume that your suitors have their own hardships, and that they're also insecure about the big reveal. Really, you're in this whole scary communication thing together.
Readers? When should she disclose the dating gap? Will it surprise anyone? Is it understandable? And what about the health stuff? Help.