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How To Make Dating Fun and Enjoyable

How To Make Dating Fun and Enjoyable

Thoughts of entering the dating world can be met with eye rolls, apprehension, and anxiety. But “getting out there” in the dating world doesn’t have to be a necessary evil when it comes to finding a long-term relationship. There are several strategies you can use to make dating fun instead of groan-inducing.

Below are 16 expert tips that are sure to make dating fun.

How to Make Dating Fun

Tip#1: Bucket List Dates

make dating fun



Not only can coming up with a bucket list make dating fun, but you can bring up the idea of “bucket list dates” on a first or second date to break the ice. In fact, making an activity out of jotting down your and your date’s ideal day or a night out together can be fun on its own. Remember that the point of a bucket list is to let your imagination run wild and ANYTHING goes.

Come up with ideas that range from things you could possibly do within the next week to things you could do maybe five years from now when you’ve saved up a good chunk of change. Bucket list date ideas could include things like:

-Skydiving

-Parasailing

-Kiss at the top of a Ferris wheel

-Exotica getaways

-Romantic day trips

-Have a splurge-tastic treat yo self day

-Go to an amusement park

-Visit an out-of-state attraction

-Carve your initials into a tree



-Kiss in the rain

-Go horseback riding

Tip #2: Adventure Dates

make dating fun

Piggybacking off of bucket list dates is the adventurous date. Using dating as an opportunity for adventuring can create a sense of exhilaration in both of you, which can subsequently increase romantic chemistry.

Here are some examples of adventurous dates:

-Have a scary good time at a haunted house (PRO TIP: jump scares automatically bring people closer)

-Try geocaching for a real-life treasure hunt

-Try exotic or intimidating foods you’ve been too scared to eat before (think octopus, anything raw, escargot, etc.)

-Go rock climbing or visit a gym with a rock climbing wall

-Go zip lining

-Visit a psychic and get your palms read (one of my favorites)

Tip #3: Volunteering/Cause Dates

Get a date and give back! Volunteer at a local soup kitchen, animal shelter, or find a cause that means something to you and your date. You can find local volunteering opportunities on websites like VolunteerMatch.org, Idealist.org, and HandsOn Network.



Tip #4: Nostalgic Dates

make dating fun

It seems that once we truly enter adulthood, a yearning for the past emerges. When a song from our middle and high school years comes on the radio, a warm sense of cheer bubbles up in us (because let’s face it, music was so much better back in our day); the sight of a Ferris wheel or merry go round spurs reveries of a simpler time, before things like rent, electric bills, and just general #adulting came into play.

In all honesty, most of us probably wouldn’t prefer to literally revisit these times we get nostalgic about. I mean, is there a person on the planet that didn’t have a horrendously awkward middle school experience? (Puberty is no joke, folks.)

Still, with generation after generation showing fandom when it comes to reminiscing, along with a plethora of recent sitcom reboots (hi, Fuller House, Will & Grace, and Roseanne), the thirst for nostalgia is real.

According to various studies, the idealization that comes with nostalgia (i.e., reframing a memory in your mind where you keep the good stuff and leave out any of the bad) is part of what causes a pull toward the past. And nostalgia can actually be beneficial.

Indulging in nostalgia can enhance mood and counteract depression. Remembering the good times of the past can also give us a sense of hope when it comes to the future.

In other words, reminisce away! And while you’re at it, integrate some sweet nostalgia into your love life to help make dating fun.

Take a trip down memory lane with the following nostalgic date ideas:

-Visit a park and swing on a swingset

-Go to a carnival or amusement park and ride a rollercoaster

-Get ice cream cones and take a stroll



-Visit an arcade

-Visit the zoo

-Play board games

Have a nostalgic movie and sitcom marathon of your favorites from childhood (bonus points if one of you has a VHS that is alive and kicking)

Go to the beach and have a water balloon fight

Tip #5: Outdoor Dates

Outdoor dates are a great opportunity to soak up the sun, get active, or simply spice up your usual dating routine. Consider the following date ideas when the weather is nice:

-Go to the beach

-Go hiking

-Check out a free outdoor concert or festival

Munch on samples at a farmer’s market

-Go on a boat ride, paddle boat, or hitch a ride on a water taxi

-Have a picnic



-Enjoy a fireworks display

-Enjoy a local fair/carnival

Tip #6: Indoor Dates

When the weather outside gets frightful, your date can still be oh so delightful. It’s typical to retreat indoors when it comes to dating (i.e., happy hours, dinner, coffee, etc.), and standard date ideas that include restaurants or cafes are great. But along with the typical bar or dinner-and-a-movie dates, there are more creative ways to make dating fun while staying inside:

-Check out an eclectic restaurant and enjoy a romantic dinner

-Go to a happy hour at a dive bar that everyone raves about as being their “favorite hole in the wall”

-Visit a chic cafe and enjoy fancy teas, coffees or juices

-Visit a museum

-Go on a brewery tour or do a wine tasting (these could be indoor and outdoor depending on the brewery/winery)

-Go to the movies

-Have your own movie night at home with good wine and fancy popcorn

-Do karaoke

Tip #7: Snowy Dates

make dating fun

Snowball? More like snow ballin’ — amirite?



If the area you live in becomes a winter wonderland, take advantage of  these snowy date ideas:

-Make snow angels

-Have a snowman building competition

-Go sledding

-Go ice skating

-Skiing

-Netflix, spiked hot chocolate, and chill

Tip #8: Holiday Dates

Using holiday cheer is a great way to get creative and make dating fun. Here’s a few examples of holiday date ideas:

-Have a romantic Valentine’s Daydinner that takes chocolate to a new level. Enjoy some chocolate fondue or go to a chocolate tasting

-See Christmas and holiday light attractions

-Have a cookout for two around the Fourth of July

-Visit a haunted house or see a scary movie for Halloween



-Find volunteer opportunities around Thanksgiving

-For Easter, find a brunch spot that has the most eclectic egg dishes

Around the new year, find a cool champagne tasting

Tip #9: Alternatives to Coffee Dates

Not a coffee fan? There are plenty of coffee alternatives that make for a great date idea. Try the following:

-Tea time at a cafe that has an eclectic selection of loose leaf teas

-Find a cool smoothie or juice spot

-Enjoy some mocktails

Tip #10: Rainy Day Dates

Don’t let the gloomy weather rain on your parade. You can make dating fun during a downpour with the following options:

-Go bowling

-Movies, dinner, happy hours, coffee (to perk up) are always a good rainy day or not

-Curl up by the fire

-Already in a relationship or been to each other’s places already? Catch up on all the shows you’ve needed to and order takeout

-Visit an aquarium

-Visit a museum



-Cook a luxurious dinner

-Go to a pool hall

-Wine and paint night

Kiss in the rain

Tip #11: Show Off Your Skills

make dating fun

If you’ve got some skills (skillz?) to show off, use a date as an opportunity:

-Bowling

-Pool hall

-Archery

-Board games (are you a jenga master? Scrabble expert? Show her how it’s done!)

-Go kart

-Batting cages



-Mini golf

Tip #12: Free Dates

You can check out 20 awesome date ideas that don’t cost a thing here. Below are a few highlights:

-Take a free DIY class at Home Depot

-Enjoy a backyard bonfire at sunset

-Take a virtual vacation using websites like 360Cities and Qantas VR

-Take a scenic drive and tour cool neighborhoods near you

Tip #13: Cheap Dinner Dates

Who doesn’t love to eat?

Dinner has been a touchstone of dating probably since dating first started. Obviously, you want to impress the woman you’re with when you take her out but would like to keep your credit score intact while doing it.

Make sure that if you’re taking a woman out to dinner (particularly if it’s for the first time), that the restaurant is nice and serves things that she likes. You can find affordable options by visiting websites like Yelp, TripAdvisor, or even just doing a basic Google search. Make sure you read online reviews before picking a restaurant.

Here are some other ways you can enjoy some good eats at a lower price:

-Make dinner at home: Prepare a fancy dinner for less by making it at home. If she enjoys cooking as well, you can up the fun by making dinner together.

-Check out restaurants that have nights with burger specials or extended happy hours where you can get some money off the total bill.

Tip #14: Let’s Get Physical

When it comes to the early stages of dating, breaking the touch barrier is an integral part of building intimacy. Finding the right times to innocuously break this barrier (putting a hand on her shoulder or forearm, for example) can sometimes seem awkward, as you may overthink when to do it.

Why not get physical with an active date? Here are some fun suggestions to naturally bring you and a date closer:

-Help her practice her swing during mini-golf

-Teach her how to play pool



-Take a dance class

Tip #15: Pick Dates That Enhance Vulnerability

I often write about how the third date is a big deal when it comes to the beginnings of a relationship. The third date is often when sexual intimacy happens, but there’s a lot more to it than knocking boots.

Whether it’s a third date or a fifth or sixth date, it’s great to be able to allow yourself to be vulnerable and show your character before committing to an exclusive relationship. This will help you and the woman you’re with learn more about each other, which will, in turn, help you build a foundation that is based on trust, mutual respect and friendship — three things that are important ingredients in a healthy long-term partnership. 

Check out these top third date questions that will help you and your date learn more about each other and that will comfortably allow you to become more vulnerable.

For the actual date, be sure to choose a place that is intimate and allows for privacy, like a quiet cafe or a nice restaurant where you won’t be interrupted. Other ideas include:

-A picnic at sunset

-While taking a leisurely walk by a scenic lake

-During a date that takes place at your apartment or home

Tip #16: Turn Dating Into an Experiment

I learned how to make dating fun when I was finishing my undergraduate degree at UC Berkley. Single and intrigued by the dating world I embarked on a 100-date experiment where I went on 101 dates with 52 different men within a year.

The process I used is called MegaDating. MegaDating involves dating several different people at once in order to diffuse energy, avoid settling for the mediocre and enjoy a plethora of different experiences through dating.

With MegaDating, every single date is an adventure that allows you a glimpse into an interesting new person’s world. Dating a variety of people allows you to open yourself to different experiences. It also increases your confidence and limits the pain of rejection because you’re not putting all your eggs into one basket.

But ultimately, MegaDating is a great strategy to help you find that one special person you can enjoy a satisfying and committed relationship with. It worked for me and it can work for you too!

Want to learn more? Head over to my calendar and book a New Client 1-on-1 Zoom session with me or one of my other coaches today.

During our session, we will create an action plan to help you reach your dating goals and overcome roadblocks that have affected you in the past. We’ll also determine if an emlovz coaching or matchmaking program could be right for you. 

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