07/09/2013 02:34 pm ET Updated Sep 08, 2013

Dating After 50: Should Secrets Be Revealed?


Science has proven that an overwhelming number of people who choose to enter the dating world after age 50 have already lived at least 50 years. And, if they are like most people over 50 (and many people under), some of their early choices in life, while not resulting in a life term in a maximum security prison, may still fall under the category of "Actions I Took Which May Have Been Beneath My Highest Possibility."

Unless you have perpetrated crimes against humanity as a youthful despot, your behavior is more than likely not a matter of public record, and the indiscretions you may have involved yourself in years ago may now be causing you a bit of conflict. Just how much do you reveal to a new partner? A few readers asked me this very question and below, you'll find their questions as well as my advice in reply:

As a very broke and self-supporting 20-year-old college senior, I donated my eggs in exchange for money. It was a horrendous experience, and I rarely speak about it. Although I assume that some children resulted, I regret my participation and do not wish to know the results. I am now 35, engaged and planning to start a family. Must I tell my fiancé that there may be teenagers walking around with my genetic material?

We suggest you not tell your fiancé. However, we do suggest that in another 15 or 20 years or so, you check in with all these offspring. There may be someone among them with the financial resources to care for you in your declining years, especially if the children you produce with your fiancé turn out to be slugs.

A friend tried stripping at a "gentleman's club" when she was just out of college to earn some quick money before starting law school. It was 30 years ago, but she still cringes (she's since become a women's rights attorney) at the memory and isn't eager to reveal this little blip in her career path to her new boyfriend. Is she wrong?

First of all, cut out the "friend" crap. We know it's you. And the boyfriend of a women's rights attorney is no less deserving of seeing his girlfriend clad in pasties and a G-string sliding upside down on a pole than some sweaty drunk with crumpled dollar bills in his paw.

Back in college, I had an affair with my instructor. Should I reveal?

Unless your grade went down even further after the affair, you can reveal this.

I have a large tattoo of Bill Clinton on my butt. Should I have it removed?

Not before you post it on Facebook.

I briefly dated several men at the same time and was having sex with all of them. What, exactly, should I reveal?

If you had sex with them individually, nothing. If it was a group situation, do you have photos? If so, please send them to this writer and a determination will be given.

In college, I once went out and ordered a glass of beer. I was underage, but the bartender didn't ask for ID. I drank the beer.

If this is the worst thing you have ever done, we suggest that you repeat your first 50 years.