Dear Diary,

Know what's rarely enjoyable at all? Blind dating. Still, I told myself that just for this one week, I'd try my darndest to be the optimist that everypony expects me to be. “Cheerilee?" I said. "You've gotta pull yourself up out of the dumps. Be proactive!”

...Yea, turns out Bramblebrush was just as thorny in personality as he is in name. Took me to Sugarcube Corner. We were four sundaes in before he decided to mention he was going Dutch.

Didn't feel so cheerful after school today, obviously. Ended class early so I could come home and mope. Big Macintosh picked Applebloom up last, so he offered to straighten all the desks for me. Thank Celestia I won't have to deal with that tomorrow morning.

Yours truly,
~Cheerilee

Dear Diary,

I guess it's my fault for supposing that a stallion named ‘Speedy’ could ever be anything but a jerk.

I'm sorry. That isn't fair. But just for the record, he was a jerk. Don't get me wrong, the date itself was fantastic. He showed up with flowers! Honest-to-Celestia daisies! They looked just like my cutie mark... But now that I think on it, exactly when could he have stared at my flank long enough to recall my daisies? Creep!

Talked to Ginger about it later. She informed me that ol’ Speedy's been shacking up with that mare, Locklove, for about four months now. Can you believe it? Ah well. Free dinner, am I right? Goodness, what's wrong with you, Cheeri? Must you always see the bright side of every awful situation?

Anyway, today might have been pretty terrible if one of my students (guess which) hadn't left a big basket of fresh apples on my desk this morning. I suppose she could tell that I needed some cheering up. The thing was so heavy, I'm still trying to figure how she carried it all the way to class from home by herself.

...Now I'm hungry for apples.

Yours truly,
~Cheerilee

Dear Diary,

I’m beginning to think that I have extremely bad luck. And I must be a glutton for punishment, because even after all this, I'm determined to ride out my week in Tartarus. Eh, I suppose it isn't that terrible.

Dammit, Cheerilee, stop it! There's no bright side when a date runs out on the check! I could barely even think straight in class today. My poor foals!

Decided I should spend lunch getting my act together, so I bought myself an ice cream cone, and watched the carts pull into market for a while. That usually clears my head. Golden Harvest chatted me up about visiting for a class presentation next week. Wish I had that mare’s mane. Gosh, it's so golden! Those Flim Flams always find a way to sneak into town every chance they get. Tried to sell me some phony good luck charm. I’m ashamed to admit that I nearly bought it. Mac from Sweet Apple Acres doesn't ever say much, really. He did start whistling that tune he always whistles whenever he spots me on my ‘moping bench’. Bit of a strange inside joke between us at this point, but it boosted my mood, at least.

I should go. I really need to plan for Goldie’s visit.

...Hmm. Maybe I’d have better luck with mares?

Blargh,
~Cheerilee

Dear deary

Bad dayte. Think I'll jus stop trying anmore. Bought some cider after school to clam down. Guess my looked really pathetic cause he gave me an extra bottle for free. Drank both.

Cheers!
~Cheeri

Dear Diary,

Well, that wasn't embarrassing to reread at all. At least I'm feeling a bit better today, headache aside. However, I've decided to give romance a rest. Class went much better for the general lack of crushing anxiety. Also, returned my bottles to Sweet Apple Acres' vendor, and thanked Big Mac for “tolerating” me yesterday. Turns out they're having a big barn dance at the farm tomorrow night. Never been to one of those, so Mac gave me the all clear to attend. I'm just going for the food, honestly. Pretty good day today, all things considered.

Yours truly,
~Cheerilee

Dear Diary,

Hey, what if…

No. Cheeri, it's time you learned your lesson about all this “bright side” business.

Dear Diary,

Just got back from the dance, aaand... maybe I'm not as unlucky as I imagined. I suppose right now it's too early to tell for sure, but I'll keep you posted!

Optimistic and yours truly,
~Cheerilee