Should I Stay or Should I Put My Finger Up Your Butt?

Dear Dategirl,

I've been reading your column for a while now, so I've noticed a few references in the past to putting your finger in your man's butt. I think a strap-on is a bit too much for me, but my heinie does need some attention. I'd love some advice on how to suggest this to my lady without grossing her out. Maybe you could share the appeal it might have for a woman to put her finger in her man's ass.

Truthfully, the only appeal sticking a digit up a man's pooper has for me is that it makes him feel good. Pushing a finger up there isn't a big turn-on, but when the person you're doing it to gets all excited, that's a rush. It's nice to be nice. Know what I mean? It's not like I find the brown eye particularly attractive and want to take pictures of it and make it my screensaver or anything. It's just a little part of the sexual repertoire. However, while I know it's all the rage in certain circles, I'm, um, not going to lick it. (I realize this puts me squarely in the "uptight" category, and I'm OK with that.)

But(t) a little finger action? Unless she's really inexperienced, I doubt your girlfriend is going to think you're freaky if you ask. Which brings me to my main point—I've found that the best course of action when I want something is to say something.

There's no need for a big sit-down. The next time you're fooling around, just maybe mention you'd like her to try and slip a finger up there. (Lube! Lube! Lube!) I hope it goes without saying—though I'll say it anyway—that rectal hygiene is of paramount importance during any kind of assplay, especially the beginner variety. Some of us are more queasy than others, and all it could take is one stray dingleberry or low-hanging hemorrhoid to put her off the anal fingerbang for life.

I recently ended a very serious three-year relationship—too serious for me at this point in my life, but that's another story. For the past two years, I've known a really good guy who I work with; he's been my work flirt, sending me messages online and stopping by my cube to say hi. He was there for me with (completely jaded) advice when I was trying to leave my ex.

We started seeing each other, and I stay at his house a few nights a week. There's only one girl at work that knows we're doing this—not because we'd get into trouble, but because we just don't want people talking about us. My problem is that before I realized how much I really like this guy, I'd made up my mind to move out of state.

I've lived in the Seattle area my whole life and really want to get away and experience what else life has for me outside this city. So now I'm faced with a decision: Do I stay in Seattle and jump from one very serious relationship to potentially another, or do I go a few thousand miles away and always wonder what could've been?

Does it really matter what I say? If I say go and you really want to stay, you'll stay. If I say stay and you're hell-bent on leaving, you'll split. And that's how it should be. You can't be asking strangers which life-altering path to take. Especially one who just spent a good hour thinking about fingers up assholes, pondering whether she should confess her aversion for ass-eating, and wondering if her brother's going to read this column aloud at the next family dinner.

What you should do is make a list. Write down the positives and negatives of each choice, weigh the pros and cons, and then decide. Or just keep fucking this guy until you get sick of him and pack up and go then.

Dating dilemmas? Write Dategirl at dategirl@seattleweekly.com or c/o Seattle Weekly, 1008 Western Ave., Ste. 300, Seattle, WA 98104.