1. How serious was it? Did they share a Facebook profile pic? Had a pet been purchased as a mutual child? Did he cry when you revealed she’d texted you first? If “yes” to all of them, then refrain. If “yes” to one, keep up the affair, but hide. If “yes” to none, then by Esquire rules, you can Tweet about her going down on you.

2. Do you gallivant frequently with said friend? If no awkward encounter at smoky, infused-vodka hideaways or wherever you “drink” can be anticipated, your conscience can be checked at the medicine cabinet. No cop, no stop, homeboy.

3. Do you contradict yourself? You do. You contain multitudes. Emerson said so. This includes sleeping with the enemy.

4. Does your friend wear a fedora? Then this was the one girl he’ll ever date. Hands off, chump.

5. Is she using you to make him jealous? Probably.

6. Are you comfortable being compared to your friend? If your cock is the kind that’ll be written about in future ages, like if your ways in bed are discussed in size 9, san serif fonts that suddenly JUMP TO ALL CAPS on previous girlfriends’ Tumblrs, then join the Litany of the Ages, Ovid.

7. Do you believe in karma? Because it’s going to take like lung cancer, your football team never winning the Super Bowl, or possibly highly publicized arrest on porn charges to balance the scales.

8. Were you in love with her first? Liar. But, it’s worth a shot.

9. Are you rich? If so, buy some new friends. If not, claim blue collar because a surfeit of socio-economic data justifies your crimes of the heart.

10. Is he the forgiving kind? Of course not. Do you read Poe? Do you know the overwhelmingly psychosomatic power of self-incrimination? Will you be able to withstand ripping up the metaphorical floorboards of your guilt for the next 40 years and showing him the sepia-toned photos of her thighs wrapped around your waist? Ha. Just kidding. You have no conscience. Have fun, Claudius.

– Dunstan McGill