We haven't checked in on young Cosmo web assistant Leo (Smith '07), in awhile. She's blogging about life as a Cosmogirl-in-Training; it's subtitled "one socially awkward girl attempts to transform into a sexy, social butterfly." Last time, we worried that her catty Hearst coworkers were brainwashing the sweet 22-year-old into becoming a typically snide, jaded young maglady. It's sort of working! Now she's wondering about "playing the field"—you know, dating a guy, but not exclusively. Is it "immoral"?

Exciting news on the Josh front. We went out again last night for drinks and we have plans for more dates! This was actually our third date, and it got much more flirtatious, and yes there was some smooching in the street.

Where is this all leading me? Well, I do have a bit of a game plan. I'm thinking that if we keep planning these dates, that I'll casually date Josh ("try him on," as one Sex and the City episode suggested) but still keep my options open. Is that immoral? Or do you think I can play the field and get away with it?

The very next week, she gives nerdo Daily Show comedian Demetri Martin her phone number after his standup routine at Union Hall! If there is only one lesson to impart here, it's this: do not blog about your relationships or exploits. (Except do, because we love it!) And if there's one thing I learned in my three short months at a fashion mag, it's this: watch your back spies are everywhere.