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Five Fun, Foolproof Date Ideas

The trick: forget the tired routines and go with a more personal approach.

Acing the perfect date ain’t easy, whether it’s the first or hundred-and-first. And let’s be honest: we’ve all been on enough near misses to know firsthand.

Admittedly, there’s a lot at stake – especially if you’re still trying to impress the hell out of your date. And sometimes things that seem like a no-brainer (like the classic, all-American movie night) can actually be the kiss of death (sitting next to a near stranger through two hours of movie sex scenes can get really awkward, really fast). But all great dates have two things in common:

  1. There’s an actual plan in place. That means no more helpless Yelp searches to find a bar last-minute.

  2. They’re tailored to the person you’re taking out.

One of the most memorable/best dates I’ve ever been on involved taking a hip-hop class at a local dance studio. It was a bold (read: highly risky) move. But it paid off – we had a great time making fools of ourselves and stole a couple moves to actually take out onto the dance floor. But what really made it a foolproof plan was that it was specific to me – what had been a passing comment about how I grew up dancing became a really thoughtful way to spend an evening.

In that spirit of thinking big, try one of these five foolproof ideas. We can't guarantee you and your date will have chemistry, but at the very least, these will give you a helping hand.


Strike Up Some Friendly Competition

Doing an actual activity will always be more memorable than a rote bar date. And there are tons of ways you can go with this.

Stay in for a few rounds of Monopoly or poker. Keep it classic with mini-golf. Go for a hipster alternative to drinking games with a shuffleboard themed bar (they exist). Or if you think your date is up for it, challenge them to a few rounds of pool or skeeball at the local arcade.

Extra points if you can find a beercade in your area – tossing back a couple pints while reuniting with the Mario Bros will be even better than it was as a kid. Loser buys the first round of drinks.


Scope Out Some Culture

If your date is a bit more worldly, look for cool cultural events in your city. Museums are always a great option, especially if there’s a cool exhibit that just opened, but don’t discount the local art gallery scene, either.

Galleries will typically do wine and cheese nights when a new show opens, so you can show off your sommelier skills while sharing your thoughts on what the hell that weird abstract painting says to you.

If you don't want something like that to be the main focus of the date, simply adding a cultural element to a happy hour date is another good option. Look for venues that have live music – whether it’s gin and a jazz quartet or beers and a local folk singer, it gives you something to pay attention to take a little pressure off maintaining a constant flow of conversation.


Get Physical

Assuming your date is the outdoorsy/adventurous type, working up a sweat (in a clothes-on kind of way) can be a good move, so long as you take care to look good and stay fresh. That means doubling up on cologne & deodorant and wearing some handsome workout clothes – no ratty gym t-shirts allowed.

Into nature? Pack a picnic and go for a day hike. Love a challenge? Check out the local rock climbing gym before rewarding yourselves with a beer. Stuck in the city? Grab a Frisbee or a sled, depending on the season, and head to the park.

Bond points for getting creative about transportation. If your city has a bike share program, pick up some wheels on your way to dinner rather than taking public transit.


Eat, Drink, and Explore

But not just at any old bar. Spend the afternoon at a local winery or doing a brewery tour instead. Not only will you get to try a bunch of different drinks, but you’ll learn something new. And probably even develop some skills you can whip out on later dates (everyone loves a man who knows his way around a pairing menu).

Think along the same lines when it comes to food. Most cities are teeming with food festivals in the summer months that put grabbing a basic meal to shame. Plus, with a wide variety of culinary options, you and your date don’t have to agree on one type of cuisine. That's a win-win.


Study Up

Maybe hip-hop isn’t your thing, but there are a ton of cool date-worthy classes to check out. If you’re dating a food fanatic, it should be pretty easy to find a cooking class in your area. But don’t be afraid to think outside the box.

If your date once mentioned they took an art history class in college, find a wine-and-paint night. If they were totally enamored with the latest Bond film, find a martial arts class to tap into your inner badasses. Maybe they’ve mentioned being bummed they never learned how to code – hello one-day workshop.


See: killer dates don't have to be expensive or extravagant. In fact, most aren’t – they’re just thoughtful. Try one out for yourself and see just how much better it ranks than another dinner-and-a-movie night.

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