How to Make Dating Fun Again

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dating fun

Jeff Harry shows you how to make dating fun again. Get inspired and learn how to play and be more vulnerable!

Want to know how to make dating fun again? Jeff Harry combines positive psychology and play to help organizations navigate difficult conversations and assist individuals in addressing their biggest challenges through embracing a play-oriented approach to work. For his work, Jeff was selected by BambooHR & Engagedly as one of the Top 100 HR Influencers of 2020 and has been featured in the NY Times, Mashable, Upworthy, and Shondaland.

In this episode of Last First Date Radio:

  • Why play is so important in dating
  • Jeff’s definition of play
  • Why dating has become a chore
  • How people can become less guarded
  • Fun play experiments you can try today
  • Why you should be ‘nerve-cited’ in dating

Make Dating Fun Again

Play is the opposite of perfection. It’s about being present.

Jeff Harry

Why has dating become a chore for so many of us?

  1. We’re striving for perfection, which is a curse. You can’t sustain it. The more we can play and be present, the better. 
  1. There are so many dating apps to choose from. You can shoot your shot on Clubhouse, too. On top of that, there’s social media that tells us we’re not enough. It’s exhausting. 

I challenge people to get bored. You can’t play when you’re sad or anxious or angry. 

What soothes you or calms you? Get out of your head and get away from TV and social media. That’s where you get your great ideas and inspiration.

People are constantly looking for the right answer, and there is none. We make it up as we go along. You have to become an expert for yourself. 

Dating is filled with so much uncertainty and rejection. How can people become less guarded and adapt a play-oriented mindset?

  • Be curious. 
  • Try to understand, not be right. 
  • Be present.
  • Another technique is reach out to three or five close friends and ask:
    • What value do I bring to your life?
    • When have you seen me be most alive?

The more we do things that make us come alive, the more we find the magic. We stop trying so hard. We start learning into our intuition to have the best answers for us. Try to take a risk every day.

What are some play experiments people can try today?

  • Play can be about asking curious questions, like “what’s the nerdiest thing you’d like to do?’
  • Take someone to three places that are important to them. 
  • It’s easy to blame others for being boring. My challenge to you is to go on a date by yourself. Maybe you’re not doing enough fun things yourself. 
  • What BS story are you telling yourself? Let it go.
  • Do the thing that makes you nerve-cited [Nervous and excited]. See everything like an experiment and see if it feels good to you. 

What’s your final advice for anyone who wants to go on their last first date?

Ask yourself, ‘does my date like me or like what I’m doing for me?’ Ask yourself how you’re showing up on dates. You are sitting on a winning lottery ticket – you – and the world needs you to show up and give others permission to show up, too. Be vulnerable and allow yourself to play.

Watch the video here:

Connect with Jeff!



Instagram, TikTok, Medium, Twitter: @jeffharryplays

Please subscribe/rate and review the podcast here.

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