in: Dating & Relationships

20 Tips to Make Dating More Fun & Fruitful

Melissa Maher

Dating gets a bad rap sometimes. We get so worked up about the outcome, we forget to enjoy the experience. Here are 20 little ways to make dating more fun.


I hit the peak of my high school career when the guy friend I was awkwardly head over heels for said “yes” to going to Junior Prom with me (yes, I asked him). But that highest high was quickly followed by the lowest low, when he proceeded to make out with what seemed like every other girl in our class.

I was heartbroken, humiliated, and clueless about how to express what I was feeling.

This set the trend for the bulk of the next two decades of my dating life: Lots of frustration with very little to show for it.

Once I figured out a few mindful (and self-compassionate) tricks along the way, though, dating actually became fun. And the more intentional I got about the process, the quality of dates rose almost as if by magic, until the wonderful man I’m in a fun and loving relationship with today sat down across from me over tapas on a blind date a few years ago.

In hopes of sparing you some of those tears and years of dragging yourself joylessly through the dating gauntlet, here are:

20 Tips to Make Dating More Fun (and Fruitful)

1. Drop expectations.

If you’re demanding that your date show up a certain way, you’ll miss the opportunity to enjoy what’s actually in front of you. Get clear on what your must-haves and deal-breakers are, but stay open to possibility. 

2. Intend to have fun… no matter what.

No more “The goal of this date is to find a husband/wife!” pressure. Keep it light. That’s where the flow gets flowing.

3. Be present.

Projecting 20 years into the future within five minutes of a first date distracts you from the getting-to-know-you process. Slow it down and let things reveal themselves.

4. Become the kind of person you’d like to date.

Is it possible you haven’t yet met the (likely insanely high) standards you hold for someone you want to date? Get good with yourself and you’ll start to attract perfect-for-you people into your life in dating and everywhere else.

5. See every date as an opportunity for some fun new conversation.

Meeting new people is fun, right? At worst it’ll make for a good story. Again, keep it light.

6. Be an anthropologist.

Take nothing personally. Observe with a curious “Hmm, isn’t this interesting” mindset.

7. Go into every date intending to learn something about yourself.

When you focus on growth, no date is a bad date. Let each experience make you an even better person.

8. View your dates as great practice for when you do meet the person you really want to be with.

Even if this person doesn’t turn out to be a fit for you, you’ll walk away with useful information moving forward. Grow and go.

9. Don’t over-analyze.

Do your friends really need to hear how it’s going while your date’s in the bathroom after your first drink together? Sit tight. Let things unfold without outside opinions clouding your own.

10. Trust your gut.

Deep down, you know when a next date is a thumbs up or a thumbs down. Follow the energy.

11. Say “yes” when you mean yes and “no” when you mean no.

No more going on a second date just because you felt too badly to say no. Clear space for the next great date to come in—no guilt required.

12. Write a dating agreement with yourself.

Create your own personalized dating rulebook. No “shoulds,” just what feels right to you. Your positive intentions will serve as a lighthouse on your dating horizon.

13. Let things unfold.

If it’s meant to move forward, it will. No need to force anything.

14. Ditch the hype.

Be mindful about letting your hopes snowball before you’ve even met this person. Take it one step at a time.

15. Don’t worry about “just being yourself”.

Get out of your head. Go on the date and just be there. Be present, intend to have a great time, and your awesome Self will naturally shine through.

16. Drop judgment.

They’re going to have quirks. You’ve got a few, too. Leave room for humanness—that’s where the good stuff is.

17. Focus on enjoying your life.

The less energy you spend worrying about meeting the partner of your dreams, the more you’ll be able to enjoy them when they actually show up. Create some breathing room so he/she can enter your life.

18. Drop attachment to outcome.

If you go into a date with the intention to be open and enjoy the process, whatever’s meant to unfold will unfold. (You clinging like a barnacle won’t turn something that’s not meant to be into something that is.)

19. Stop comparing your dates to your exes (or anyone else).

Give this human being a chance to reveal themselves.

20. Trust the process.

Relax. No need to rush. Let things unfold. When it’s time (according to the universe, not your ego), the right relationship will come.

Try on a few of these practices and you’ll likely find yourself where I eventually did—on a date with an amazing person who it might just turn out will make this whole dating thing worthwhile.

Cheers to your success in love and life.

About the Author:

Melissa Maher Melissa Maher

Melissa Maher is a Certified Professional Life Coach who takes a mindful approach to helping busy-brained women live in the moment, express their desires unapologetically, and love the bodies (and selves) they’re in today. She created the soul-supportive Joy Surfers Club in her mission to help women live a life full of possibilities and love on their own terms. Melissa is also a Registered Yoga Teacher, Certified Nutritionist, and dedicated Vipassana meditation practitioner. She lives in beautiful San Francisco with her boyfriend. Connect with Melissa through her website or on Facebook or Instagram

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