It’s a funny — and by funny I mean awkward — situation when you’re sitting across from a friend at dinner and can’t help but be distracted by the huge piece of lettuce engrained in the center their perfect, orthodontist-approved smile. You hope that the next time your friend takes a swig from their soda, the lettuce will miraculously disappear. But to your dismay, they push away the cup to pursue a conversation with their crush seating directly behind your table. So now your friend is conversing with the love of their life and a huge piece of green foliage is caught in the middle of a $2,000 grin. When your friend turns around to gush about how great the conversation went, you start to twitch.

“Oh, he’s so cute,” your friend will say. “But why was he giving me such funny looks? He kept on staring at my mouth. Cosmo said that guys get very turned on by a girl’s lips. Do you think that is true?” All you can do is nod in silence and excuse yourself to the bathroom. You failed as a friend. You should’ve told.

Life is rough enough as it is. That’s why you count on friends and the altruism of strangers to help you get by. Not everyone has the time to eat with enough care to guarantee that all food imbibed will actually be digested and not end up as a dental fashion applique. It is your friends who pull the toilet paper from your feet upon exiting a public restroom. It is your friends who tell you to hit the treadmill when you gain a little weight (if not friends, then surely hypercritical mothers). You count on your friends to be your mirrors when no reflection is nearby, your scales when you’re too scared to actually venture atop of one, and your superegos when your ids are taking control.

Nonetheless, there are certain etiquette rules to abide by. Because honesty sometimes can hurt. And other times it’s unwarranted. Hence, this column is a tribute to a tricky question that underlies many awkward situations — when to tell?

Foremost, as exhibited by the prior example, it is utterly imperative to notify friends at all times when food is misplaced in their teeth, hair or face. Do not let friends wander the rough and tough streets of New Haven as human billboards advertising what’s to eat in the dining halls today. Never assume that they’ll check a mirror before exiting a dining hall or restaurant. Just because you’re vain doesn’t mean your friends are. Plus, you never know if a friend has a job interview or an important meeting immediately following a meal.

However, on the note of food, it is not necessary to point out the huge and unfortunate stain a friend has acquired after noticeably spilling food or drink all over him or herself. You’ll only make them more uncomfortable if you dwell on it. However, if your drunken fraternity brother has uncontrollably peed all over his khaki pants while out partying, informing him of his stain is a kind gesture. That way he’ll either change into another pair of pants before passing out and puking in his bed, or he’ll pass out right there in his piss-stained khakis, providing ample opportunity for embarrassing photos — which will increase the general utility of the group.

For boyfriends, everyday is a test of “When to Tell.” My words of etiquette wisdom? Always tell your girlfriend that she looks great. Even if she came back from studying abroad fifty pounds heavier, tell her you’ve never seen her look better. Do not let your girlfriend’s follow-up, “Are you sure?” deter you from your mission. Always compliment and you’ll come out a champ.

Finally, friends ought to tell friends when they don’t look their potential best. As long as you have alternative outfits or suggestions to offer, honesty is appreciated. However, if your friend is walking out the door to go out, yelling to them as they get into the car to “reconsider the outfit” is futile. In such cases, refer back to the previous paragraph. Likewise, it is merely cruel to tell a guy that he’s balding when it is an uncontrollable part of college (for the unfortunate prematurely balding sect of men, at least). However, if you suspect that a friend might be prone to balding in the future after having dinner with his comb-over dad, slyly slipping a few pills of Rogaine into his pocket is both an appreciated and pragmatic gesture.

Finally, it is KEY to tell your friend if her skirt is tucked into her underwear; especially if she’s walking to her seat in a Psych lecture of almost 400 students with her skirt ever-so subtly imbedded in her Calvins. Although this certain girl eventually felt the draft and realized that her assets were exposed to the lucky viewers in the back of the room, the gasps as she walked down the aisle were not quite loud enough to convey the message.

Yalies, stand up and help a girl out! Friends don’t let friends walk around with their asses hanging out. I know — I thought it only happened in the movies, too, or in Seventeen’s “Say Anything” column. But let me tell you firsthand — the danger is real. Too real. Really real.

If this or any other unmentionables happen to a friend of yours, please do them a favor and practice proper etiquette: Tell.

Dana Schuster swears never to tuck without looking again.