Simple Activities that Make a Great First Date (and a Few that Don’t)

Rachel Brewson

I have dated. A lot. Of course, most of those were first dates that fizzled from the start. You know the type, where you’re already looking for an out before you even sit down? Dating in the city is hard. Sure, there’s an endless supply of suitable single men, and a whole mess of activities to choose from for a first date, yet it somehow complicates it all. Who would’ve thought that would be a problem? Hopefully you won’t be as stubborn as I was and can learn from my mistakes expertise, and not have to fumble through oh so many awkward situations. I’ve made a quick list of great and not-so-great activities to consider for your first date!



GREAT: Drinks at a place neither of you have been

I don’t get why guys these days avoid this old classic so often! Maybe they feel it’s too cliché, or not creative; but there are so many great bars to explore that it’s hard to go wrong with this classic first date. Why not try out a new bar? You’re on a date with a new guy, right?? Going to somewhere completely new can help you take in the experience as a couple. When you’re both strangers and no one knows how long you’ve been together, you can have whatever kind of night you wish! It also helps keep it on neutral ground, rather than one person showing the other something they already enjoy: you can both create a new memory together! It’s also nice to know that you’re less likely to risk bumping into anyone you might know (or someone you might be trying to forget) since you’re not heading to your favorite haunt. I prefer to keep my favorite bars sacred anyway, you don’t want to create any bad memories from a dud date at your favorite place to grab a drink!



GREAT: Coffee and a walk around town

One of my favorites! Especially when it’s chilly outside! There’s not much better of a first date than a simple cup-o-Joe-to-go and the arm of your first date as you stroll along the boardwalk in Santa Monica. The sounds of the crashing waves, the crisp ocean breeze and a warm caramel macchiato will leave you in a blissful trance. Also, his coffee choice could be your window into his soul. Is he a drip? An Americano? Maybe he’s a fancy cappuccino man! Face it; you’re going to be overanalyzing everything on a first date, might as well have some fun with it, right? And, who knows… Maybe the caffeine will come in handy later 😉




GREAT: Pretend to be tourists!

Before you roll your eyes, let me ask you this: what could be more fun than seeing your city through the fresh eyes of a tourist? Even if you and your date have lived in the same place forever, you can have a ton of fun enjoying all the great tourist traps in your city together! I mean, how many times have you driven past that wax museum and not given it a second thought? The best part is you’re almost guaranteed a few new profile pics! Tourist traps are built for souvenir photos. So, ham it up and have a blast! Why not?



GREAT: Movie in the park

Movies in the park are really popular these days! (And super romantic, if you do it right) 😉 No matter what city you’re in, there’s a pretty good chance there are outdoor movie showings of some sort. They provide all the makings you need for a cute, romantic, and fun first date. Typically I don’t like going to the movies on a date because you’re forced to sit and be quiet, effectively ending all interaction with your date besides maybe some hand holding, or awkwardly trying to make-out like teenagers in the back. But with an outdoor showing you can move around, have a snack and some wine, and if the movie is boring just crawl under the blankets for a little romantic smooching! Just make sure you learn from my mistake: Bring extra blankets for warmth and cushioning for your caboose! It can get chilly at night, and the ground can get mighty hard after a couple hours. Pack an easy to serve meal, sneak a little wine in your basket (just make sure to get a screw top if you don’t carry a wine opener with you everywhere you go), and you’ve got the makings of a storybook evening in the park!




DON’T: Full-Day Activities (Amusement Park, Zoo, Day Trip Out of Town Anywhere)

I know I don’t want to be stuck in a lengthy activity with a date I just can’t stand. A day long activity will make your first date end up feeling like a marathon. You always want to be able to pull the plug and walk away when you realize there just isn’t a connection with your date. Disneyland might sound like a romantic first date, but trust me; it can begin feeling claustrophobic pretty quickly. If you do find yourself getting asked to the Happiest Place on Earth, then you might want to see if you can make it a group date. If you have some of your friends along for the day, you might feel a little more comfortable.



DON’T: Bookstore

It may seem like a good idea at first. A bookstore is a public place and you can leave at the drop of a hat if the guy ends up being weird, so what could be the problem? Well, the entire date can quickly become a pop trivia quiz as you wander aisle to aisle. Don’t get me wrong. I think sharing your interests is a really important thing to do! And you want to feel comfortable to share on your first date. But a bookstore can make the conversation overwhelming really fast. You can bounce between subjects with every step. And that can quickly lead to a lopsided and potentially harsh conversation. Suddenly you find you’re getting grilled on why you don’t like Harry Potter. Why you haven’t read Freud. And how on Earth could you have possibly bought 50 Shades of Grey?


Photo Credits:

BAR Spirits TOKYO by sayot (CC-BY)

Tourists Taking Selfie – Central Park by Eric Gross (CC-BY)

Autry night sky by Sharon Sperber (CC BY-SA)

Prater amusement park by night by Nicubunu (CC BY-SA)


Rachel Brewson
Editor, Dating

Rachel Brewson, Dating Editor, has played matchmaker and dating coach to friends and colleagues, as well as written for xoJane, Thought Catalog and a handful of online blogs. She loves craft beer, the beach, and warm LA nights.