Dear Sara,

Last year, my crush seemed to be at least mildly interested in a relationship
with me, but I didn’t want to start something right before summer break,
so I waited. Earlier in the fall, I made overtures (not explicit) to ask her out
earlier this year, but she always replied with “I’m busy this weekend, maybe
next.” She now has a boyfriend who goes here. Needless to say, finding out about that kind of broke my heart. As it stands now, I’m happy as long as she’s happy, but there’s a part of me that hopes that someday I might have a chance. Here’s my problem: I’m supposedly going to meet this boyfriend in the near future, and, since she at least considers me a good friend, my crush has asked me to tell her what I think of him. I’m sure I’ll have mostly good things to say,but I don’t know how to handle the situation. I feel like if I say only good things and “he’s great!” then I’m destroying any future possibilities, because if he’s great, why would anything ever change? There’s also a part of me that says that anything bad that I say will strike my soul as just telling her something bad so she’ll think less of him, so I really don’t want to do that. I don’t know what to say if she asks me! My mental instincts shout “the truth, silly!” but my aortas say something else. Help!

—Love-Confused Confidant

Love-Confused,

I understand your dilemma, but unfortunately, there’s really only one solution. You’re in the dreaded “friend” category, and the only way out is to be absolutely the best friend you can—no one ever starts dating their friends they think are just okay, and you’ll be lucky to even stay friends if you start acting like a jerk around this girl. No matter how much it might feel like you’re shooting yourself in the foot, you’ve got to suck it up and be honest about the boyfriend when you meet him. I’m not saying you have to go overboard with compliments, but a sincere “he seems really nice” is the right way to go. Of course, if he seems like a total tool, don’t feel like you have to praise him, but avoid criticizing him outright. Exclaiming, “what a Neanderthal!” will not make her realize she’s actually in love with you and has been all along, but it probably will make her reconsider her choice in friends. If he’s obviously not suited for her, be neutral, and above all, supportive—no doubt she’s a smart girl and will figure this out herself without your help. Seeing her through this relationship, for good or bad, will ultimately be to your advantage, no matter how much it sucks at the moment. There’s a reason why women love “When Harry Met Sally,” and it’s this: we all secretly want to fall in love with our best friend and live happily ever after. So be supportive, be a good listener, and remember that sometimes old adages are true—good things do come to those who wait.

Good luck,

Sara

Dear Sara,

I have recently had an awkward email encounter with my concentration’s
department program administrator, wherein she intimated that I was mentally
unfit to write a thesis and outright told me that my “status as an honors
joint concentrator is in serious jeopardy.” What’s more, she sent this e-mail
to me 24 hours before the first 20 pages of my thesis are due to the department— talk about bad timing. What is an appropriate response? Mail-bombing the Barker Center? Poisoning the tea at the department’s next poorly-named, poorly-attended social gathering? Feeding her pets to lions? I’ve already drafted a few e-mail responses, but I’m afraid they might be a bit extreme. Any help would be welcome.

—Eaten Alive by English

The moments left until that 4pm deadline are ticking away as I write this, Eaten Alive, so I hope that you were able to meet the deadline without too much stress. It’s unfortunate that your department coordinator was so unsympathetic, since thesis writing is stressful enough to turn even the most model student into the class dunce. But, don’t despair, I think I can guide you to the perfect email for use in this situation. Try this:

To Whom It May Concern: I realize that I’ve been stressed and have fallen behind on my thesis this semester. I apologize. I’ve made a commitment to re-prioritize my time, which includes the following measures: 1. Drinking only every third day, insteadof every other. 2. Only watching Oprah
when something really good is on, like Oprah and Gail’s road trip. 3. Sleeping
past noon only in the event of actual necessity, i.e., illness or a particularly rainy day or the like. Please give me another chance. I’m really serious about my commitment to the study of the handkerchief in Jane Austen’s novels.

Or this:

Dear Sir or Madam: The study of time in Faulkner’s major works has invaded my life and become my passion. One unfortunate side effect is my complete inability to consider the future, much like many of Faulkner’s characters. Emulating Quentin in The Sound and the Fury, I’ve destroyed my watch and begun wandering through Cambridge, searching for my lost youth. Please understand that while my level of understanding grows deeper each day, my connection to these texts is tenuous at best, and cannot be disturbed by such time-anchored requirements like “chapter deadlines.” I’m sure Faulkner would agree with me when I say that artists don’t have time to listen to critics like you. In fact, he may have said that himself. I can’t even remember anymore. Please see the attached 20- page sentence; I think you’ll find what you seek. I’m off to ponder my shadow on the footbridge.

Or even:

Dear Glorified Secretary: How dare you. Where’s YOUR honors degree? That’s what I thought. As you can see, there are many options.  I’m sure you’ll find one that strikes the right tone for the occasion, as well as
the upcoming holiday season.

Happy writing!
Sara

—“Dear Sara” runs on Mondays this semester. Send letters to DearSara@thecrimson. com. Letters will be published anonymously.