5 Fun Dates to be Wildly Overdressed For!

It’s date night with your guy! And since it’s finally his turn to plan a “surprise date” for you, here are some fun ideas that you will be overdressed for, because you didn’t totally know the plan and now are so overdressed and oh god you feel so stupid.


A Walk Through the Park!

Aw, Dan remembered spring is your favorite time in the city! You had imagined a date holding hands during a beautiful sunset walk through the blooming trees in your cute floral print flats. Unfortunately by “walk” he actually meant, “a hike upstate” and now your feet hurt, your shoes are ruined, and your makeup is melting off your face. What a surprise!



Dan asked you to “look nice,” so you went all out with a bodycon dress and some classy nude stilettos. Too bad those heels keep sinking into the mini-golf course! Just try not to flash the children as you awkwardly bend at the knees to scoop your ball out of the 8th hole. But look how cute Dan looks in his t-shirt and jeans!


Friend’s Birthday Party

He said it was going to be at “a restaurant downtown,” so you of course interpreted that as the perfect opportunity for your new floor skimming maxi dress! And you could have sworn you saw him reaching for that new blue button-down you got him. But as it turns out he was actually reaching for his old college lacrosse penny and has a very loose definition of “restaurant,” because now you’re at a sticky dive bar full of 18-year-olds. Hold up the hem of your dress and down a shot with your free hand to let him know, “I really thought we were going to dress like adults tonight.”



Gallery Opening

So Dan said something about a “gallery” to describe where you’d be going, but he did not say it was a paint-and-wine party with 50-year-old women wearing sweatpants. Dan could have at least told you to take that gown off before you left the house in a cocktail dress, but isn’t it great to have a man who plans things?


His Brother’s Wedding

There is no way you can misinterpret this one! Everyone knows a wedding is the perfect excuse to go out and buy a fancy new dress, which is exactly what you did. What a bummer that Dan neglected to tell you that this “rustic” wedding was actually just a chill weekend camping with their family and closest friends. Dan’s wearing a patchwork plaid cotton blazer and you are by far the most overdressed person here in your event romper and wedges. What a fun way to get to know his family!


No matter how different the date is from what you expected, remember that you look great and he tried! Forget all the people who are staring–they’re just jealous because they don’t have a thoughtful, if poorly communicative, boyfriend like you do. And next time, stuff an extra pair of shoes in your tote, just in case.