08/29/2013 06:13 am ET Updated Oct 29, 2013

How Soon Should You 'Tell' On Yourself?

Sorry I've been out of touch for a while. It's been an interesting few weeks since I last wrote. Much has happened. I will share that with you, as best I can, in the next blog. Right now I want to pose a question that has been on my mind for a while. As always I would love to hear your own experience and opinions in this area.

So here's the big question: when should you share your biggest secret with someone you met online? I am not talking about someone with whom you have just been emailing back and forth, or even someone you have spoken to numerous times. I am talking about someone you have met in person, had the first meeting -- what I call the interview date -- and now you are on to dinner, or dinner and a movie; maybe already at a third encounter in a more intimate setting, whether it's a restaurant, coffee bar or the apartment or house one of you live in.

You like each other, though it's still new with much more to discover. How tempting it is to get to the elephant in the room! But is this the right time? Or should you wait until the budding relationship deepens a bit more?

I was on a third date with a lovely man. He had just cooked me a delicious dinner in my home. Being a non-cook, or at least someone adept at burning food for lack of attention to what is happening in the kitchen as I merrily sit and write in another room, I did truly appreciate his preparing and even serving us a meal.

After the dessert, I rented a great movie (you must see "What Maisie Knew") and we enjoyed it. As we sat discussing the movie he said, "This could get serious, you know." I said, "If it does, is that a bad thing?" "Well," he replied, "If I am ever going to stay over, there are a couple of things I need to tell you."

Okay here's the thing: what came next could have waited -- at least for a few more of his yummy home-cooked meals. Then I might have felt differently about his confidences. I will not be specific, but let's just say that one has to do with his manhood and the other has to do with the apparatus he has to wear to bed at night to not die in his sleep. As for the first reveal, again, I might have been more accommodating to what this poor guy has to do each time he wants to... participate, and do right by his partner. And even though he minimized the process involved in what he called "accommodations to growing older," which they surely are, they were not something I felt comfortable about. You may not agree. You may think I should have at least let him stay over for one weekend to see how those two things played out, but I couldn't do it. With no investment in the relationship it was just easier to walk away. Yet his former love had apparently not had a problem living comfortably with either of these specific "accommodations" for some years before her death.

On that self-same couch I have had gentlemen callers "confess" (if that's the right term) to having a chronic disease, to having no money, to having been used by women they met online, to being clinically depressed, to needing surgery, to being quite a bit older than they said they were, and to not trusting women anymore. They have also told me horror stories of their painful divorces, their estrangement from their children, having false teeth they have to take out at night, and how truly great they are at oral sex, which, they promised, will "rock my world." By the way, rereading this sentence, there is no connection between the last two items listed. Or maybe there is!

What's most interesting is that these secrets-or things that probably should have or could have remained secret for a much longer time -- were all told to me on the first, second or third date. Whichever of those it was, it was usually the last date.

And boy do women do the same thing! I have heard similar or worse stories from many men, who reported that early on some of the women then went out with confessed to being desperately lonely, desperately broke, had no use for sex anymore, had "a mild case" of herpes, (but it was "under control cause they could feel it coming on"), had "dried up down there," drinks "a bit too much," lied about not smoking, had some scars they wanted you to know about before they got undressed, missed their late husbands, hated their cheating ex-husband, had grown children with serious problems, were on anti-anxiety drugs, and were ten years older than they said in their profile.

One woman, I was told, confessed to her dating partner (this happened in one of the southern states; both were on that she was wanted for murder. But, she insisted, it was "a bum rap because I didn't do it." This was on a first date, and the man said that as she was finishing that sentence his hand was up, signaling for the waiter to bring him the check.

What's the real point here? My point is, why tell on yourself so completely and so soon? Do you really want to chase every single candidate away before they have an opportunity to become vested in your wonderful personality, your generosity, charm, talent -- the unique goodness of you? Yes, getting old sucks. There is a price to pay. The machinery breaks down bit by bit. It happens to everyone. Why focus on that? The reason we do it is very clear and very human: if you can accept my worst fault, my worst scar, my worst challenge, we can get past that and be on equal footing. I won't be scared to invest too much of myself, only to be discarded down the road. So here's my big reveal... NOW!

Makes sense on the one hand. On the other hand, I believe in putting your best foot forward for as long as you can. That thing is not you. It is just a price you are paying to be alive at this point in your life -- and not such a bad price, most likely, compared to what some others have to pay. So why scare someone away before they are enrolled in you?

What do you think of that?

I will leave you with this wonderful passage from the Velveteen Rabbit by Margery Williams that I used to read to my daughter.

"What is REAL?" asked the Rabbit one day, when they were lying side by side near the nursery fender, before Nana came to tidy the room. "Does it mean having things that buzz inside you and a stick-out handle?"

"Real isn't how you are made," said the Skin Horse. "It's a thing that happens to you. When a child loves you for a long, long time, not just to play with, but REALLY loves you, then you become Real."

"Does it hurt?" asked the Rabbit.

"Sometimes," said the Skin Horse, for he was always truthful. "When you are Real you don't mind being hurt."

"Does it happen all at once, like being wound up," he asked, "or bit by bit?"

"It doesn't happen all at once," said the Skin Horse. "You become. It takes a long time. That's why it doesn't happen often to people who break easily, or have sharp edges, or who have to be carefully kept. Generally, by the time you are Real, most of your hair has been loved off, and your eyes drop out and you get loose in the joints and very shabby. But these things don't matter at all, because once you are Real you can't be ugly, except to people who don't understand."

Earlier on Huff/Post50:

Survey On Post 50s Dating Issues
Survey On Post 50s Dating Issues