Tessa brings up issues with which I've dealt.
I've had two marriages, two children, and two divorces (not in that order, btw). Whenever the subject comes up I'm happy to tell friends about my children, and grandchildren. I can do that because my family has accepted me unconditionally. The fact that they all live 2,000 miles away means there are no unexpected meetings between my family and my friends where questions could cause one of them to unintentionally out me. No one has asked about my exes. If the subject came up I'd say I prefer to talk about happier times.
Of much more difficulty for me is hiding the time I spent in the Army—three years, tour in Vietnam. That time did not define who I am, but it informs my attitude toward things such as those who managed to avoid military service, yet are enthusiastic supporters of sending other people's children to war. It hurts to hold my tongue, but I do. When asked if I spent time in the military I say, "No!" and hope I'm convincing. The only American service women who served in Vietnam, as far as I know, were nurses. I have almost zero medical knowledge—I'd have a hard time lying about that.
I've tried to keep my story as simple as possible so that I never have to remember who knows what about my past. I'm happy to share my work history, which is probably the only opportunity for being outed. But I have no interest in lying. So far I've been fortunate. If my house of cards comes crashing down I'll deal with it. I'm at an age where passing (no, the other kind) has become something I contemplate. I feel I owe all my friends an explanation for why I worked overtime to deceive them (I didn't, but some will feel that way). I've begun work on a letter I'd like read at whatever memorial service I get in the hope that most won't defile my memory.
That's how I handle stealth. It works for me. I hope anyone who chooses anonymity finds a way to make it work.