I was incarcerated for a little over nine years for a property crime. So the obvious is, of course, obvious, but even before that my last girlfriend was in 1991. I am not one who is into one-night stands or fly-by-night relationships, and I am definitely not desperate. I have been out for over a year and am getting my life back in order. I have built up enough confidence to start looking for a relationship despite my current situation. The only thing that's bothering me is my imprisonment. I want to be honest with my next "special lady," but at the same time, I don't want to scare her away. I am truly an honest person and don't want to feel like I am deceiving anyone. So, my question is—do I tell her on the first date, or do I wait so she sees that I am worthwhile and then tell her? Oh, and in case anyone wants to know, no, I never "bent over and picked up the soap."
A scandalously underrated talent is the art of keeping one's lips zipped. Discretion is the better part of something or other, and I'd suggest you exercise it in this instance. Now, I'm not saying you should fib to your "special lady" (who is hopefully a classy little lassie with a sassy chassis), but you should choose the moment to break this news to her very carefully.
That moment would absolutely not occur on your first date. First dates are for scamming, I mean charming, the other person into thinking you're the most amazing guy she's ever met. They're for feet-sweeping-off-of, copious amounts of liquor, and assloads of compliments. So like I said, don't tell her on the first date. Unless it looks like you're going to sleep with her that night.
I once dated a guy who had herpes. Well, more accurately, as something like one in four people are afflicted, I've probably dated many more, but he was the only one brave enough to tell me about it. He did not share this fact with me over appetizers, dinner, or dessert, but he did tell me before we got naked together. We were making out on my sofa when he pulled away from me and got a somber look on his face. He looked down at his lap and sat there quietly for a few seconds.
"I need to tell you something," he said, finally making eye contact.
My guts clenched up, and I started to sweat. Being a worst-case-scenario kinda gal, my first thought was that he was going to tell me he either had a terminal disease, was married, or had suddenly determined I was too ugly to kiss anymore. (I never said I was normal.) So, as you might imagine, herpes came as kind of a relief.
I suggest you employ a similar technique in your situation; wait till after you've gotten to know each other, but before you start sleeping together. I'm sure you realize that time served will be a deal breaker for a lot of broads, so prepare yourself. But also realize that people get rejected all the time, for crimes as paltry as having oddly sculpted facial hair or freakishly small hands. I've been rejected for any number of reasons. I would normally list these reasons ad nauseam, except I'm trying to turn this into a high self-esteem day.
On the other end of the spectrum are those women who will actually find your unfortunate incarceration a big fat turn-on. I mean, c'mon—look at all the serial killers who get married in prison! If indeed you were locked up for something as dull as a "property crime" (which, P.S., must've been a helluva property to net you nine years in the slammer!), just be mysterious about it. Come up with something more romantic—like, say, armed robbery—and watch 'em slobber.
In closing, Z, I'd like to thank you for clearing up the anal-rape question. If it's any comfort, shockingly, that hadn't even occurred to me, but now I've got an Oz fantasy going on in my head that just won't quit. . . . Because of you, now I have to run out to the store for more AA's. Damn!
Questions? Write Dategirl at firstname.lastname@example.org or c/o Seattle Weekly, 1008 Western Ave., Ste. 300, Seattle, WA 98104.