The Breakup

In my estimation, I’ve been dating—and breaking up—since I was 10. My first boyfriend was in the fifth grade, and I’m pretty sure he broke up with me by asking his friends to tell my friends that he didn’t want to do the Walk with Israel (a charity walk sponsored by the Jewish United Fund) with me. In my world, that was pretty harsh. I give that breakup a 10 on the rude scale.

In junior high, things became a little more complicated. I fell in love with my seventh grade boyfriend, the cutest boy in school. We dated for two years—until I found out I wasn’t the only…

If Not Now, When?

Ah, new relationships. As exciting as they are, when you’re in your 30s, there’s more pressure to make responsible decisions. You’re not young enough to get away with certain behaviors (so long, flings) that would fly in your 20s; every move you make could come back to haunt you—and sooner rather than later. This new person in your life could be the one you’ve been waiting for all along, so you don’t want to mess things up…

Out There

When the brilliant and erratic Jeff McCourt founded the Windy City Times in 1985, he began a 15-year run that changed the way gays were regarded. But his volcanic personality caused countless rifts, and he died this year at 51, largely alone.

Head of the Class

Not to beat a dead horse, but I had two more bachelorette parties this past weekend as part of my international wedding tour (the last wedding of the season takes me to Rome in October). If my estimation is correct, that's two feathery boas, three tiaras, countless penis-shaped suckers and straws, lots of lacy lingerie, … Read more