Priest

What makes sleeping with a graffiti artist great?
Because we always invoke that “How'd he do that?” sense of awe.

Are graffiti artists more daring in bed?
Depends on the writer. Some guys have a marker in their pocket; I've got a fire extinguisher filled with two gallons of Blaze of Glory Red, if that makes sense.

Does someone’s skill at graffiti make them more attractive or compensate for deficiencies in other areas?
Being a good graffiti artist will not make up for any shortcomings — unless your turn-ons include sleeping alone between midnight and 5 a.m., bailing your boyfriend out of jail, and acting as a watch-out every time you two walk down a street together. But for my sake, I hope it does.

I've always wanted to make my girlfriend some kind of art piece as a present, but I'm a little worried it'll come off as cheap. Thoughts?
If you love her, spray it somewhere on her route to work. The bigger the better. If you get nicked, you can always claim you're Banksy and thousands of people will come and take their pictures in front of your piece. Then someone will cut it off the wall with angle grinders and sell her name for millions. Who's cheap now?

I secretly creep the Craigslist 'casual encounters' section behind my girlfriend's back. At first it started out as just a fantasy, but I've been contacting people and moving steps closer to consummating the thing every time. Is this innocent as long as I don't actually do anything or is it a bad sign?
Wait, Thomas? Is that you? I thought you said you were gay.

Is there any tactful way to initiate the idea of anal with my girlfriend? I've had quite a few people tell me "just go for it," but I think that could only end poorly.
Tell her it was the only way that your ex-girlfriend got off. That will bury a seed of curiosity and jealousy deep inside her anus that only your thrill-drill can retrieve.

I'm sleeping with this girl, and the sex is out of this world. She's strongly hinting that she'd like a relationship and I don't. I really don’t want to break things off. Do you think this is setting me up for a meltdown?
Generally these these things tend to work themselves out... in small-claims court. You've pretty much described eighty-five percent of all relationships. Lawyer up and go for gold. Worse-case scenario, it doesn't work. No one in Vegas said, “I put in five dollars and won three-hundred grand."