10/25/2010 04:16 pm ET | Updated Nov 17, 2011

Fifty First (J)Dates: Should I Keep My Relationship To Myself?

No, this is not another revenge on John Mayer song written by Taylor Swift (hers is entitled "Dear John." Really brillz wordplay there, T-Swift.)

Sometimes, peeps be askin' me fo advice. I'm good at giving it, mostly because I'm good at writing/talking. In excess. (Feel free to email your dating question(s) about anything from being less religious than he is to what color jeggings go best with the new Chanel ballet flats from this season to

Today's question comes from "Private Penny." I am sort of picturing myself as E. Jean from Elle Magazine, except without the Botox (and the 50+ years she has on me.) I do like her, because she is a tough cookie and manages to do her job for Elle, unlike Olivia Palermo. Who is Satan spawn. I digress:

Dear FFJD:

I am super private about my dating life and unlike my friends, just never really want to 'tell all' at any given point. Maybe its because I haven't been in that many serious relationships, but I kind of don't think its anyone elses business. If and when anything progresses past the 3 month mark (note: ha like preg trimester) I think then I'd be more likely to share with others because it would be more solid and facebook status changing.

In particular though, my parents and sister as well as my friends always want to meet the new beau and I feel like that's traumatic to them. Or, I guess I'm concerned none of the beaus is properly qualified (read: jewish, doctor lawyer)? Anyway my sister who has been in a serious relationship forever, takes any casual references to a "date" as a betrayal becuase she's just not privy to intel. What do you think I should do?

Private Penny

PP - I am enjoying the alliteration. I am doubting your name is Penny, most likely Shekel, but whatever.

You are certainly in a pickle, Penny. I get it.

Some people are just not "sharers" about personal stuff. Some of my friends love to pick apart every detail of a new hookup, whereas some would just like to keep it to themselves. It depends on the person and the situation.

It sounds to me like you're wary of the commitment it requires to truly make someone your boyfriend (which I understand is very scary, because that label comes with a lot of Louis Vuitton baggage.) We're all scared that once we declare someone a significant other for our friends or family that we've spoken too soon. Unfortunately, there's almost no way of knowing until you do it.

I understand that you're a private person, and I really respect that. But you don't need to worry if someone is "good enough" for your parents or your friends. At the end of the day, it just matters that he is good enough for you. Your friends and family just care about your happiness. If your Mom or your brother decides to pick apart someone you are crazy about, that really has nothing to do with you. Successful, more type A women (such as yourself, and many wonderful girls I know) are often obsessed with finding the "perfect" person. Perfection is a myth. And as cliche as it sounds, the "perfect" person would also be incredibly boring.

I think you should talk to your sister and tell her that you want to let her in to your dating life (if you do) but she needs to understand that you two handle relationships very differently and that she has to respect that.

I only have a brother, but I have numerous friends with the "perfect older sister" scenario who seems to always have it all figured out (with a serious boyfriend or husband). She probably doesn't. Your family just wants you to let them in. And I think you should, but in different ways than boys until you're ready to introduce them to your wonderful new dude.

And be proud that you're one of the few 20-somethings left on the planet who values privacy and utilizes it.

-The FineMC via FFJD. (E. Jean was already taken.)