Here’s the thing about dating: No two dates are the same. The setting, the stage of the relationship, and oh yeah, the person you’re sharing cocktails with never form the same combination more than once. Chances are that you try to take all of these variables into account when deciding what to wear on a romantic rendezvous, a thought process which can lead to a migraine, hair-tearing madness, or worse. Which is why the ole straight-forward What to Wear on a Date style advice story just doesn’t do the trick.

And that’s where I come in.

Every week, I’ll outline a dating situation—hypothetical of course, but don’t blame me if it borders on eerily familiar territory—and supply some suggested attire.

Now, granted this isn’t the usual GlamChic fare, but admit it; you’re intrigued. And the second you stop looking for outside opinions on your sartorial decisions, I’ll cease to offer mine. Until that day comes, read on, consider yourself saved—and feel free to email me with your own “hypothetical” quandary:

First things first: This is not a date. Or at least you don’t think it is. It’s a “group thing,” which you think is maybe the number 1 romantic buzz kill of all time, but regardless you’ve agreed to suck it up and meet the ever-expanding gang at the local sports bar to watch the playoffs or whatever it is. Your reward? The opportunity to spend more time with J; a die-hard Red Sox fan, a bespectacled advertising VP, and your current friend-crush.

You’ve known J for a few years; you went to the same college but didn’t know each other then. (How that could have happened—considering your quaintly Arcadian alma mater—you don’t know.) When you first met, after graduation, you had been dating some debonair young law student who was Boring with a capital B, but really, ridiculously cute. You thought J was nice and smart and all, but a tad too nerdy for your taste.

Now, a few years later—and with the experience of a few more lame lawyer-type boyfriends under your, ahem, belt—J’s low-key geekdom has become distractingly attractive. But you’re afraid that he still considers you an old-school chum, one who only dates the dashing and dumb. You want him to see you as someone more than a friend, and someone who is as thoughtful and down-to-earth as he is. And you need him to start seeing this way A.S.A.P. before the sexual tension (which you think is SO there) kills you. You know that clothes clearly don’t matter to him—you recently saw him wearing a corduroy L.L.Bean button-down and not in the ironic, hipster way—but you’re hoping to catch his eye somehow.

Unfortunately for you, baseball will be the only thing on this boy’s mind tonight. But since you’re crushing so hard, I know that won’t stop you from trying to make a good impression. In that case, take cues from TV’s most unlikely style icon, My Boys’ PJ Franklin. The sportswriter character is forever surrounded by boys, and her laid-back approach to fashion is something to strive for given your current predicament.

Jordana Spiro as PJ on TBS’s My Boys

Ella Moss top, Shopbop

Don’t bother with anything frilly or flirty; you’ll only look out of place in the neighborhood saloon. Go for cute cotton top in a dark color. (Brights scream LOOK AT ME while subdued shades can speak volumes about the wearer’s low-key confidence.)

Hudson Jeans, Couture Candy

Well-tailored jeans fit the bill, but make sure you like how your rear looks in them as the whole bar—including J—will get a good look when you ask the bartender for a fresh pitcher.

Saks Sweater

Since it’s still officially fall, skip the jacket and slip on a cozy sweater. That way, even if nothing happens with J, you can channel Ali McGraw in Love Story to get all tingly.

Thorn Tab Necklace, Shopbop

Skip the bedazzled accents; You don’t want glittering gems to distract anyone from the bar’s glossy flat screens. But if you must, try a whimsical necklace to get conversations going during commercial breaks.

Edelman Flats, Urban Outfitters

Flats flats flats; it doesn’t matter what color, make, or model just slip them on. Sporting heels in a baseball-watching bar scene makes you 1)Look uber-obvious about your reason for swinging in the ole sports bar 2) liable to receive a round of well-deserved teasing from your aforementioned friends.

And whatever you do, don’t wear a Red Sox hat unless you’ve got a Massachusetts license or are card-carrying member of the Daughters of the American Revolution; You may play with a boy’s emotions, but you can’t pretend to like their team.

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