Dear Anna,
Is there a way to break up without breaking up? — Lost
Dear Lost,
Is this a Zen koan? If not, reach out to your queer women friends. I guarantee you one of them has been paradoxically breaking up with an ex for the last several years.
Dear Anna,
Is it weird to be a woman going to a straight friend’s bachelor party? — Stag Hag
Dear SH,
Only if you’re secretly in love with your straight friend and want to sabotage his potential marriage by, I don’t know, getting him drunk and instigating an orgy with several strippers. Otherwise, nah. It’s just a party. Have fun! Don’t get too drunk, be respectful and tip generously.
Dear Anna,
I’ve been sleeping with a recent divorcee for a few months. I’m a 28-year-old man. She says she wants to know “where our relationship is going” but I don’t think we’re even in a relationship. We hook up, but we aren’t exclusive, and I prefer to keep things that way. Do I tell her this? — Crossed Lines
Dear CL,
Uh, yeah, you should tell her this. She’s clearly operating under a pretty big misapprehension here and it would behoove you to be honest, so she can make an informed decision and either keep hooking up with you casually or find someone who wants to be in a relationship that’s going “somewhere.”
As an aside, I don’t know why people get so panty-twisty about the word “relationship.” Even if you’re casually hooking up, that’s still a relationship. A casual one, yes, but a relationship no less. A dating relationship is defined broadly as “an emotional and sexual association between two people.” You’re not signing a blood oath or anything. So don’t fear the word itself. And don’t fear your divorcee either.
Lay your cards on the table. Even if it means you might not keep getting laid.
Dear Anna,
Is there a term for when you perform oral sex on someone while she’s on her period? — Inquiring Minds
Dear IM,
I don’t think collective humanity has settled on a name for that particular situation.
I offer the following suggestions, however.
—Code red
—Parting the red sea
—A wonder down under
—Riding the crimson wave (thanks, "Clueless")
—Eating red herring
—Taking a redeye flight
—Choosing the red pill
—Going with the Flo
Anyone else have ideas? Send them to me at, ahem, redeyedating@gmail.com. I’m here for it!