30-Day Dating Challenge Ideas That Will Transform Your Dating Life

30-Day Dating Challenge Ideas that will Transform Your Dating Life

I’m a big fan of 30 day challenges – I actually quit meat and alcohol for good by starting with a 30 day challenge. I’m currently on a 200 day streak of learning Spanish on Duolingo (and still going strong), which started this way. I started daily journaling this way and it’s now three years later. All these things have improved my life. Some in tiny ways (I can order food and book hotels in Spain, yay) and some monumentally (I look and feel much healthier and younger now I’ve given meat and booze the old heave-ho). It’s worth saying here, I didn’t intend to give up either of these things for longer than a month when I started. They both just stuck and now it’s a commitment I’ve made to myself.

How we spend our days is how we spend our lives.
– Annie Dillard

Why a 30-Day Challenge?

So yes, big change can happen in just 30 days. Thirty day challenges are a great way to create a new habit, change up how you do things, experiment, try new things, shake things up and, yes, improve your life in tiny or sometimes monumental ways.

Thirty days is a sweet spot to try something new or remove bad habits and replace them with good ones.

Too short – it’s hardly challenging. Too long – we lose interest (think New Year’s Resolutions).

Why a 30 day dating challenge?

All this got me thinking. How would it feel to bring some of this energy and action into your dating life? Who knows where it might lead.

So many people say they don’t enjoy their dating life. They find it stressful, painful at times and well, not a lot of fun.

Dating should be fun though. I always say, if you’re not having fun, have a break from it. It sounds like you need it.

A 30 day dating challenge can be playful, experimental, educational and hopefully a lot of fun. And could end up transforming how you feel about the whole dating experience.

Remember though, you aren’t doing this challenge to meet your soulmate. You are doing it to throw yourself into the middle of life; to chuck out your rule book; to rewrite your dating story; to discard your checklists; to challenge your expectations;  to take risks; to accept the sting of rejection; to show up as your wonderfully weird self; to be ghosted; to feel cherished; to feel butterflies. This is the joy and beauty of life.

How does a 30-Day Challenge work?

There are two ways of taking a 30-day challenge.

One is to take a new activity every day for 30 days. See idea 12 for Inner Circle‘s 30 day dating challenge.

The benefit of it is you introduce something new to your life every day. This kind of 30-day challenge is more about spicing up your life.

The other way is to carry out specific activities every day for 30 days straight.

These activities chosen by you are your challenge ideas.

These challenge ideas can be anything. So long as they have a positive impact on your dating life.

What are the benefits of a 30-day (or monthly) challenge?

1. 30 day challenges are fun. We compete against ourselves playfully and engagingly, which is the best kind of competition.
2. It shows us the scope of what we can do when we create intention.
3. Tracking progress is easy (and fun). You just check in with yourself everyday and take note of how you’re doing.
4. Challenges push us to make positive changes in our lives
5. Completing the challenge each day increases our sense of accomplishment and our self-confidence. And this feels good.
6. Committing to a challenges ensures we make incremental improvements each day.
7. We become our own accountability partner and that is special. It means we can motivate ourselves to achieve positive things in our lives. Making and keeping promises to ourselves are the most important promises we make.
8. Changing up how you do things even for just 30 days can result in big mindset shifts and behavioural changes.

1. Send a message to someone new every day

I started with a challenging one. This one is about feeling uncomfortable connecting with others but doing it anyway.  On the other side of this, you’ll feel so much more relaxed about reaching out to others online. Seeing each message for what it is, a simple chance to connect with someone new. No expectations beyond that. Creating new connections, however brief, will be rewarding and may lead to more interesting opportunities, if you keep your heart and mind open. And if they go nowhere, well, it’s no biggie. You have another 29 opportunities to explore.

2. Quit the dating apps and throw yourself into a new, fun pursuit instead.

It may seem counterintuitive to stop your dating app activity for a dating challenge. I hear that. But by focusing on something new and fun instead, you’ll push yourself out of your comfort zone, learn more about yourself and may learn to love yourself even more. This growth will have a big positive effect on how you date when you’re ready to get going again.

3. Make the most of free trials and try a new dating app every week

There are so many apps out there and lots of niche ones too – like Bristlr, which says it connects those with beards to those who want to stroke beards. Or Dig, the dog person’s dating app. The key here is experimentation and fun.

4. Let a friend take control of your dating activity for the month

Scary as hell this one. But why not. Choose that friend wisely, though! This is a great way to get used to not being in control. We can’t control much of what happens in life and it can be helpful to accept what happens and make the most of it.

5. Take yourself on a date each week.

Julia Cameron, in her book The Artist’s Way, outlines one of her favourite tools, the Artist’s Date. It sounds fancy but simply put, she wants you to do something that intrigues or delights you for an hour or two weekly. In other words, she wants you to play. The rules are simple; it needs to be planned in advance, which shows you value yourself just as if you were planning a date with someone else. It’s a stand-alone activity that you do on your own.  It lasts for a couple of hours. Stuck for ideas? There are loads of blog posts dedicated to ideas for the Artist’s Date.

You may be thinking you’re not an artist so it wouldn’t work for you. Trust me, you don’t need to be an artist to experience how wonderful this experiment is. I did this challenge for 12 weeks and, among other things, I fell in love with forest bathing, dancing and yoga as a result. All of which I still regularly include in my life, eighteen months on.

This one is my personal favourite as it allows you to devote time to yourself and discover more about who you are, what you’re into and ultimately what you’re about.

6. Read a blog post or watch an Instagram reel daily from a dating pro

Research the best dating experts, matchmakers and dating coaches like James Preece, and give yourself the gift of dating know-how. You might learn about how to set effective boundaries, how to boost your confidence on a first date, which photos make the best dating profile pictures ever and so much more.

7. During this month, commit to saying yes to every social invitation

This one personally fills me with horror. I’m more likely to be finding excuses to say no to anything social, especially in the winter months. But, the 30 day challenge is all about creating change, doing things differently, trying a fresh approach (even if only for the 30 days to see what happens).  I couple of years ago I listened to the audiobook The Year of Yes by Shonda Rhimes. Dang, she’s inspirational and so is this book. She got up off her couch and took her life to the next level. To be fair, she was already living a pretty amazing life, but this is how to cranked it up even further.

8. Rewrite your profile capturing the absolute best version of you and date for a month.

Rewrite your profile as though you are someone who is 100% comfortable about who you are and love everything about your life. Grab a friend and get some dating photos while you’re still in this mindset. Now try dating for a month with this new dating profile.

9. Try rejection therapy 

Rejection therapy is a thing. It has the power to transform you from someone who actively avoids rejection and all the ‘pain’ that comes with it, into a fearless, confident adult who takes rejection in their stride.

Jia Jiang took on a bold but super transformative 100 day challenge, The 30-Day Rejection Therapy Challenge. By seeking out rejection for 100 days straight – from asking a stranger to borrow $100 to requesting a “burger refill” at a restaurant – Jiang managed to desensitise himself to the pain and shame that rejection often throws up. What is magical about this challenge is that during the process, he discovered that simply asking for what you want can open up possibilities. Life was suddenly opening up in unexpected ways. I can’t think of a better mindset to help you enjoy online dating.

10. Attend a Meetup group each week.

If you live in a city – in the UK or US – there are plenty of meetups geared up to help single people meet in a variety of informal ways. Or just join a meetup that is aimed at one of your passions. Or try something new and discover a new passion. It’s easier to attract people when you’re living and loving your life.

11. Create a simple affirmation

I’ve recently reread Kamal Ravikant’s book, Love Yourself Like Your Life Depends on it. It’s a little piece of magic. If you haven’t read it yet, this would be the perfect 30 day challenge to kickstart the rest of your life.

Kamal shares his experience of creating and repeating the affirmation “I love myself”in his head over and over until he rewired his brain. He shares his meditation technique and other steps he took to really embed it.

It’s kind of obvious why this is going to help your dating life. If you see everything through the lens of loving yourself, life is so much better and you start attracting people to you.

His book is a super short read, but can create a massive transformation.

12. The Inner Circle 30 day dating challenge

Inner Circle has created this 30 day dating challenge because they recognise it’s a great way to shake things up.

Check out the full challenge list here:

13. Do a plank for 5 minutes every day.

Nothing like a rock-solid core to make you feel hella good for your dates.

14. Learn how to rewrite your dating story

Rewriting your dating story is basically about shifting your perspective.  It’s about questioning your interpretations of your dating life.  It’s about growth.  A lot of our narratives began when we were young and they are still guided by that young version of ourselves. As we grow older and gain more life experiences, we learn and grow (hopefully). 

Taking the time to reframe our stories is a way for our mature self to put aside our childish interpretations and grow more fully into our new reality. It will involve letting go of old limiting beliefs about yourself and the world around you and getting some perspective

15. The 30-Day Gratitude Challenge

Of all the challenges I’ve listed here, this one is probably the easiest one to do. But despite the simplicity of this challenge, the results are surprisingly powerful and effective.

How to start? You just need a new notepad and pen and for the next thirty days, you commit to spending a few minutes a day writing down three things (or alternatively everything) you feel grateful for. Some days are easy and you can think of loads of things. But some days are definitely harder than others. On those days, go back to basics. Sometimes the things I’m grateful are sipping my cup of tea on the window sill, the air I breathe, how much I love dancing to the song I’m listening to.

16. Discover new dating podcasts and listen to an episode every day.

Head here to check out some of our favourites – old and new. Learning from experts will help you up your dating game.

17. Meditate for 5 minutes a day.

Mediation makes everything better.

So what do you think?

I hope you like the ideas in this blog post.

When you start a 30 day dating challenge, you’re making a promise to yourself.  When you keep that promise to yourself, you more than likely boost your self-confidence. I love doing 30 day challenges because at the end of them, I feel really proud of myself and happy that I’ve achieved something. More importantly, my confidence usually soars.

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