Remember that scene in “Pretty in Pink” where millionaire crybaby Andrew McCarthy picks up poor, pouty Molly Ringwald at work for their first date and he’s like, “Do you want to go home and change first?” and she’s all, “I already did …”? OH, SNAP.
That’s just embarrassing for everyone involved, and it pretty much sets the tone for their tortured affair.
It also brings to mind the question of what to do when one member of a dating duo is dressed for a night at the opera while the other is wearing something more suitable for a late-night emergency run to Wal-Mart.
Generally, it’s good practice never to leave the house for a meeting with that special someone wearing any of the following:
1) Anything you’d wear to bed, the car wash or the gym
Yes, there are dates that call for T-shirts and jeans. (Bowling, anyone?) But unless you’re waxing pickup trucks as part of a charity car wash during your date, avoid jean shorts, your disintegrating Chucks and your favorite threadbare T-shirt. This also goes for “lingerie-inspired tops” (nobody’s buying that) or anything terrycloth/bedazzled across the butt. It’s not to say that these things don’t have a place, but there’s nothing worse than feeling under-dressed if spontaneous plans take you someplace where flip-flops would be frowned upon.
2) Something you’d wear to a wedding
This isn’t a hard and fast rule, and if you know you’re going someplace where it’s appropriate, it can be fine. But be sure to do your research — say you meet a guy at a tapas bar you’ve never been to, thinking it’s the perfect excuse to get another wear out of that silk cocktail dress. But when you arrive, you realize it’s more of a taco joint than a tapas place — and everybody else is wearing hoodies and jeans. Do your recon work, check online reviews of the place, and ask around before you overdress.
3) Shoes that make you walk like a jacked-up stripper with bunions
Always make sure you can actually get around on your wheels before your take them for a spin. This doesn’t just go for high heels — this goes for pinchy flats or just-a-bit-too-big sandals that you bought online that make you endlessly flat-tire yourself. What if he suggests an après meal gelato and you end up having to walk eight blocks to get there? Your feet might well be bloody stumps by that time. Bloody stumps: not hot.
4) Any article of clothing that unzips, slips or bursts open unexpectedly
Yes, this seems like a no-brainer, but we all have that skirt that breaks hearts but occasionally unzips of its own accord. Anything strapless? Probably not a good idea either. Because you will spend all evening hiking up that tube top. Do yourself a favor and jettison it from your first-date arsenal completely.
5) Anything you haven’t worn before
It’s incredibly tempting to just run to Anthropologie after work to buy something off the rack because you suddenly hate what you wore to the office. But you have no way of knowing if this dress has a loose button, or if there’s some ridiculous ruffle you didn’t notice, or if when you sit it suddenly reveals the tops of your upper thighs. Stick with something you’ve road tested.
The point is, plan ahead. Sure, any guy who freaks out over what you wear probably isn’t worth the trouble, but hey — if you like the guy, you can only score points by dressing in a way that says, “Hey, I’ve put some thought into this, because this evening is something I’ve been looking forward to, and it’s important to me.” It’s the polite thing to do. Dressing appropriately and in a way that makes you feel put together and confident only sets you up for success.
Your best bet: Think of the date like a job interview: You want to look like yourself, but even better (if that’s possible). Find out where you’re working (eating, drinking, bowling) and dress for yourself, but crank it up a little. And if he shows up for the date dressed in frayed cargo shorts, well, maybe you didn’t really want to go to try that fancy hotel bar (or see him again) anyway.