Dating Diary

There are pros and cons to documenting your every date in a diary. Here, one woman makes a book out of hers.

By Anna David

My journal used to be the recipient of all my dating woes. No boy I had a crush on or went on a date with or kissed was safe from being analyzed, obsessed over, and potentially torn apart somewhere in the pages of my most trusted object.

But then life interfered. I began writing for a living, making the idea of pouring all my hopes and dreams about my love life--or lack of one--roughly a thousand times less appealing. Dumped? Feeling suffocated? Obsessed? It seemed far more practical (not to mention easier on my poor overworked hands) to burn up my cell-phone minutes chattering away to friends about these thoughts and issues.

Samara O'Shea never abandoned the whole journal thing, despite the fact that she, too, writes for a living. The creator of letterlover.net--a service she provides where she writes letters for those who have the occasion but not the words--and author of For the Love of Letters: A 21st-Century Guide to the Art of Letter Writing, O'Shea has diligently kept a journal for most of her 28 years.

And now she's sharing her journals with you. Her latest book, Note to Self: On Keeping a Journal and Other Dangerous Pursuits, not only shares snippets from her own journals but also contains passages from the journals of such luminaries as Sylvia Plath and Anais Nin (if you know anything about Nin, I probably don't need to warn you that hers get a bit racy).

But O'Shea has learned firsthand that the journal isn't always a wholly safe depository for confessions. "I had been with my boyfriend for two years and had been cheating on him for about two months," O'Shea recalls now of an incident she writes about in Note to Self. "I was acting aloof and distant, and my boyfriend sat me down and said 'There's something wrong here.'"

While O'Shea didn't come clean, she did confess the details of her affair--with the sous chef where she was waiting tables--in the pages of her journal, which her boyfriend, looking for answers, gave a read. He confronted her and she agreed to call off her affair, but the two broke up and moved out of the apartment they shared a month later.

Still, all was not lost. The boyfriend, a stand-up comic, incorporated what happened into his routine ("As painful as it was to read, she's a writer so it was actually really well written--it was like, 'This is a page-turner--I wonder if this dude's going to find out she's cheating on him'"), and the two have been friends ever since. And we can now witness the entire experience by watching O'Shea's trailer for the book.

Despite the fact that I don't have such interesting escapades to report (cheating, like journal writing, is simply a part of my past), my friends still get earfuls of my dating joys and woes. Because a journal, no matter how pretty the outside and well-lined the pages, can't stand in for the friend who's going to tell it to me how it really is.

And also, with friends, I always know my secrets are safe.