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How to Be Less Awkward on a Date by Being Playful

How to Be Less Awkward on a Date by Being Playful

How to Be Less Awkward on a Date by Being Playful

Are you wondering how to be less awkward on a date with a girl you like? If so, consider making these dates more playful.

If your dates feel like work or if they feel forced, ask yourself how to make them feel more natural. A date isn’t a day of work or a job interview, so it shouldn’t feel like one. 

According to an article from Psychology Today, being playful is underrated and extremely important when you’re an adult. Moreover, playfulness during a date can actually increase chemistry and make you seem super sexy on a date.

The reason for said sex appeal is because:

-It makes you come off as nonaggressive, which puts a woman’s mind at ease.

-It exudes youthfulness and health.

Take a look below at some surefire ways to be less awkward on a date by being more playful.

How to Be Less Awkward on a Date Tip #1: Have an Activity Planned

how to be less awkward on a date

Instead of just “winging it” on a date or expecting the environment to set the mood for you, have an activity planned and ready to go when the date starts. This will show her that you took special consideration during the planning process, which is sure to impress.

And by having an activity that you can both be busy doing — and bonding over — you seriously reduce the chances of awkwardness.

One date spot I really like is The Warming Hut in San Francisco. This is a place is great for sitting and chatting over light fare and also lends itself to some outdoor options. You could bring a fishing pole, stack some rocks with your date, jump on a bike, go on a hike, or jog over the Golden Gate Bridge with your date. If you don’t live near San Francisco, find a similar location and replicate these activities. 

Another example could be something like frisbee golf. If you plan something like a walk and picnic in the park, you could have this set up ahead of time and enjoy some friendly competition.

When it comes to choosing an activity for a date, choose something you’re interested in, but don’t worry about being an expert on it. Simply having an activity planned makes the date fun and focuses more on the energy of the experience, rather than on thinking up random questions to ask, or figuring out ways to fill awkward pauses.

Take a look at the following articles that will help you plan a fun and exciting second date:

Physical Second Date Ideas that Get You Moving

-30 Second Date Ideas That’ll Knock Her Socks Off

Tip #2: Focus on Fun

how to be less awkward on a date

Make the date fun for both of you — not just her. If you’re not having a good time, she’s not going to be having a good time. Finding yourself feeling “meh” about the activity you’re both participating in on your date can invariably be one of the things that leave you wondering how to be less awkward on a date, when in fact, not making a conscious effort to have fun is what made the date awkward in the first place.

When researching date ideas, look for things that would scream “Fun!” to both of you. One of the ways you can do this is by focusing on common interests and coming up with a date that plays to those interests.

For example:

-If you both have an interest in arts and culture, look for a cool and slightly unusual museum.

-If you both are adrenaline junkies or extreme sports fanatics, consider taking a kiteboarding or air trapeze class.

-If you like to be active and get your heart pumping without feeling like you’re working out, take a dance class.

-If you’re all about holistic wellness, take a partner yoga class.

-For more, here’s a list of fun date ideas to get you started. 

Tip #3: Focus on the Feeling

how to be less awkward on a date

If you’re wondering why am I awkward around the girl I like OR how to be less awkward on a date, think of ways to not only make the date playful but to make it feel playful. You can do this by using a few different strategies:


Making a woman laugh will eliminate awkwardness and increase chemistry. Not sure if you’ve got the proper comedic chops to split her sides  that’s ok!

If being funny isn’t something you consider a strong suit, watch comedy shows or sitcoms and steal one-liners. I used to borrow lines from Modern Family all the time on my dates, and no one ever realized it!

Paying attention to funny one-liners also helps you to learn comedic timing, which can be super helpful when dates start getting awkward. It’s important to keep the mood light and fun. Remember, dating should never feel like an interview or a job.

Tease Her

Another way to make the date feel playful is by gently teasing her as a form of flirtation. Make sure that the teasing is always light and positive because it can be easy to accidentally tread into a sarcastic territory. If you use teasing to put her down (i.e., don’t yell “IN YOUR FACE” or say, “Wow, is this your first time?” when she gets a gutter ball during a bowling date), it’s going to come off as mean and throw off the entire mood.

Use teasing as a way to make things feel more playful by saying things like:

“OK, I gotta know  how do you pull off being beautiful, funny and sweet all at the same time?”

“Does this mean you’re starting to fall for me?” Say this if she stumbles a bit on a crack in the sidewalk or something like that.

“This is why we can’t have nice things!” This is always a great line to pull out either when something VERY minor has happened (like she drops her napkin) or after something a little more embarrassing (like her dropping a drink) happens.

Going back to sarcasm, the reason that I advise you steer away from sarcasm (which is different from playful teasing) is that it can come off as hostile or even bullying behavior, despite the fact that you may have been using it to lighten the mood.

According to an article from Psychology Today, a majority of people who receive sarcastic comments feel put down and think the person saying them is a jerk.

Here’s an example of a sarcastic interaction you could end up having with her.

Her: Did you want to grab one more beer?

You: No, I’m just going to have lukewarm tap water. Yes, of course I’m getting another beer.

Kind of cringe-y, right? Sarcasm is honestly hostility dressed up as humor, so make sure you stay away from it.

Playfully tease in an affectionate way and always remember to smile, be kind and tease when it feels natural.

Play Games

Games aren’t just for kids, but including games on your date can create a nostalgic and fun element. Here are a few games that you can play depending on the date:





-Arcade games

-20 questions

Would You Rather?

Make sure that you pay attention to the mood of the date and let the environment naturally dictate whether or not playing a game is appropriate, or if it will simply disrupt your other activities.

Tip #4: Choose Locations That Are Naturally Playful

how to be less awkward on a date

Pay attention to the environment if you want to learn how to be less awkward on a date.

Choose locations that are naturally playful. For example, you could grab a coffee near a park and ask her when the last time was that she jumped on a swing set was. If she seems interested, you can enjoy swinging for a bit or even push her on one of the swings, which is flirty and sweet. If you’re in a park setting, you could also do something like challenging her to a race to a nearby tree or lake. 

Being outdoors during a date is also awesome because it naturally stimulates positive energy and good conversation.

Another location I really like for nostalgic dates is a bowling alley. Not only is bowling fun (regardless of whether or not you’re good at it), but there’s typically a lot more to do than just bowl. You could go to an arcade or challenge her to a game of pool or skeeball. Some bowling alleys even have bars with karaoke nights, which would be a great way to be playful, silly and even show a little bravery.

How to Be Less Awkward on a Date: Wrap-Up

When it comes to learning how to be less awkward on a date, MegaDating is one of the prime strategies I recommend to my clients. MegaDating is a dating process that involves dating several different people at the same time in order to decrease stress and anxiety by diffusing your energy and keeping your social calendar full. It also helps you naturally learn how to be less awkward by giving you practice in the dating world.

Getting a lot of experience when it comes to dating can help you build confidence because you realize that there is plenty of fish in the sea and the pressure to settle for the mediocre (or a partner that you’re not truly compatible with) diminishes over time.

I used MegaDating during my 100-date experiment to find a compatible long-term partner. It worked for me and it can work for you too!

Need some help to reach your personal dating goals? Book a new client 1-on-1 Zoom session with me or one of my coaches today. During our session, we’ll discuss your dating goals, create an action plan, and see if our matchmaking or coaching services is right for you. 

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