Planning dates should be easy, right? 

But for most of us, dates are a huge stressor. You’re trying to present your best self + suss out who the other person really is + assess if there’s chemistry there … while trying desperately not to trip, get food in your teeth, or say something stupid.

If you’re single (or know someone who is), we’re here to help. Read on for our best tips and tricks to planning a great date.


TIP #1: Do Something Playful

Having fun is sexy. And sexy is good.

According to psychotherapist Esther Perel, a lot of lust revolves around playfulness. So when planning a date, don’t just do what feels “adult”; do what brings you genuine joy and even laughter. Our top date ideas:

  • A comedy show
  • Bowling
  • A bike ride
  • A magic show
  • Mini-golf
  • An arcade
  • An amusement park
  • … or channel the movie Ghost and hit up a pottery studio 

Couple bowling together

"Dude, don't whisper in my ear when I'm rolling". (Source: New York Gal)

TIP #2: Have Some Backups

It’s a good idea anyway, but in the era of diseases that rhyme with Shmovid, you probably want some alternate date ideas in your back pocket. 

One of us at The Deep once planned a first date at a nice restaurant in Boston. Our date had no food allergies, but they randomly mentioned they hated the taste of cilantro. Little did we know that the place we picked literally specialized in cilantro-based dishes. 

Those were an awkward first few minutes. Fortunately (for us and our date), the restaurant across the street had (cilantro-free) sushi.

We got lucky that time (not in that way – get your mind out of the gutter). But looking back, we should have had a couple of other restaurant options – and reservations – on hand.

The same goes for activities: nothing ruins your perfect beach date faster than a sudden rainstorm. And think you’ve nailed it with your plan for a quiet picnic in the park? Think again when you meet the crying/screaming monsters at Tyler’s 3rd birthday party right next to you. 

GIF of an overly excited kid at a birthday

Take it easy, Tyler. (Source: Tenor)

TIP #3: Money Doesn't Equal Successful Date

Sure, it’s nice to flash some Benjamins (do the young kids still call them that?). But there are plenty of cool dates you can go on that won’t cost you a penny.  

Obvious ideas: go for a hike, hit up a (free) museum, or walk around the city at night – sticking to the safe areas, obvi. But there are probably a bunch of random, cheap activities you could do as well. 

Some ideas: go pet the puppies at an animal shelter (pro tip: make sure your date isn’t allergic first), get cheap tickets to the nosebleed section of a baseball game, or our personal favorite: pack a picnic – or stay in – and play The Deep Dating Edition.

Paying on a date with a credit card

Pro tip: Most restaurants do not accept library cards. (Source: Nasdaq)

TIP #4: Go Deeper

Ever been on a date where the most you found out about the other person was where they are from, what they do for work, and how many siblings they have? Come on – you could’ve gotten that info on social media in 10 minutes. 

Dates are a chance to really get to know the person AND help them get to know you. But how do you do that, while also keeping things flirty + fun? If you want to try and thread that needle: we got you.

In a bit of a cram? Start with 4 of our favorite questions to ask on a date.

The Deep's Dating Edition is awesome. We should know.

Time to get out there and plan your next date! … Though ideally you should meet someone first (we’ll leave that one to the dating apps!).

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