Reboot Your Love Life with this 30-Day Dating Challenge

Transform Your Dating Life in 30 Days with a 30-Day Challenge.

I’m a big fan of 30-day challenges. I’ve done many things by starting with a 30-day challenge, from losing my baby weight to waking up early, increasing intimacy with my husband (which he loved), reading books, gaining skills, etc. I’m on a 100-day streak of learning Spanish on Duolingo, which started this way. Daily journaling is now part of my life two years later. All these things have improved my life in small and big ways. I never intended to give up any of these things for longer than a month when I started, but they just stuck and became a commitment to myself.

Why Try a 30-Day Challenge?

Have you ever wanted to change your life significantly but felt overwhelmed? The good news is that big change can happen in just 30 days. Thirty-day challenges are a fantastic way to change positively and shift your actions. Thirty days allows you to experiment, try new things, shake things up, and create a new habit or break an old one. It’s not too short that it’s hardly challenging, but it’s also not too long that you’ll lose interest. Think of 30-day challenges as a way to check in with yourself and take small steps toward creating the life you want for yourself.

Why a 30-Day Dating Challenge?

It’s time to challenge yourself and get out of your dating rut! Dating can be a stressful and painful experience, but it doesn’t have to be that way. After hearing so many people complain about their dating lives, I created a 30-day dating challenge to help get you out of your funk and make dating fun again!

Setting Intention and Self-Competition

30-day challenges are a great way to set an intention and challenge yourself playfully and engagingly. It’s easy to track progress, and you can note how you’re doing every day. The challenge of pushing yourself to make positive changes can be rewarding, and completing a challenge each day can be incredibly satisfying and build your confidence.

Accountability and Mindset Shifts

When you commit to a challenge, you become your own accountability partner. It’s essential to make and keep promises to ourselves, and 30-day challenges are a great way to do that. Even if you’re trying something new for 30 days, you can experience monumental mindset shifts and behavioral changes that can stick around even after the challenge.

Before You Start

At the end of the challenge, you might not have found your soulmate, but you will have gained something more valuable – an appreciation for the joy and beauty of life. You will have taken risks, accepted the sting of rejection, shown up as your wonderfully weird self, been ghosted, felt cherished, and experienced butterflies.

So What Are You Waiting For?

Are you ready to throw yourself into the middle of life? To chuck out your rule book, rewrite your dating story, discard your checklists, and challenge your expectations? Let’s embark on a 30-day dating challenge that will be playful, experimental, educational, and hopefully fun!This is your chance to make a change and prove to yourself that you can do it. Choose a challenge that’s meaningful to you and get started. Who knows what you could accomplish?

Your 30 Day Dating Challenge

Day 1: Spring Clean your Dating Apps

Chances are your dating apps are a cluttered mess. We get it. With potential matches, it can be overwhelming to keep track of who you’ve matched with and who you haven’t. That’s why we’re here to help you with Day 1 of our Dating Challenge: Spring Clean Your Dating Apps.

How Does it Work?
It’s simple: unmatch the people you’re not interested in. This will help you sort through and find the ones you potentially are interested in, and reignite the conversation, making this dating challenge a hell of a lot easier!

• Start by making a list of the people you’d like to unmatch.

• Go through your dating apps and take action. Unmatch those who don’t make the cut.

• Don’t forget to follow up with the ones you’re interested in. A simple “hey, what’s up?” can go a long way!

Related Reading: 8 Expert Tips for Finding Love in the Digital Era

Day 2: A Surprise Date: Step Out of Your Comfort Zone!

It’s time to challenge yourself and explore something new! Why not add a little adventure to your life by going on a date with someone who wouldn’t usually be your type? Taking a chance on someone different can be a great way to connect and discover something remarkable. Who knows, they might be the exciting end to your endless dating life!

Tips to Make it a Memorable Date:

• Be open-minded: Keep an open mind, and don’t let preconceived notions about your type stop you from having a great time.

• Be adventurous: Try something new and exciting together – it can be a great way to break the ice and make memories.

• Be yourself: Just be your wonderfully weird self- totally honest and authentic, and you’ll have a great dating story!

Related Reading: Learn How To Create An Unforgettable Date Night

Day 3: Reignite the Spark: Go on a Date with an ‘Old Flame’

Are you feeling the itch to reconnect with an ex-partner? Before you take the plunge and reach out to them, take the time to think about why you’re doing it. The goal here is to reignite the spark, not to rekindle a flame that burned out for a reason!

Here are some tips to make sure your date is a success:

Steer Clear of Negativity
Negative energy can quickly kill any good vibes. When you meet up with your ex, do not bring up any reasons why the relationship didn’t work out in the first place. Instead, focus on the positives and the good memories you shared.

Take It Slow
Going on a date with an ex may seem like a romantic idea, but it’s important to remember that it’s still a first date. Don’t expect the relationship to pick up exactly where it left off. Take it slow and enjoy getting to know each other again. Reigniting an old flame can be a great way to reconnect with someone you care about. Just remember to stay positive, be open-minded, and take it slow. Who knows, it may be the start of something new and beautiful!

Related Reading: Best Questions To Ask To Get To Know Someone 

Day 4: Write a Love Letter to Yourself

We all know how important it is to be kind to ourselves and to take time to appreciate all we have accomplished, but sometimes it’s hard to put those words into action. That’s why writing a love letter to yourself can be such a powerful exercise. Read on to learn how to write a love letter that will lift your spirits and make you feel like the amazing person you are!

Start by Writing a List of Your Strengths
Take a few moments to think about all your unique qualities and skills. What do you bring to your relationships, your job, and your life? Write down whatever comes to mind, even if it seems silly or small. List all the things that make you proud of yourself. These can be personal traits, achievements, or anything else that you value.

Incorporate Anecdotes or Stories
Think of times you’ve gone above and beyond or done something remarkable. Maybe you received recognition for a job well done or you stood up for something you believed in. Writing a few sentences about these experiences and how they made you feel will add a personal touch to your letter.

Don’t Forget to Be Self-Affirming
Include positive statements in your letter that will remind you of your worth. These statements should be specific to you and the unique qualities that make you who you are. For example, you might write about how you’ll never give up on yourself, no matter what. Or, you can write about how you have the courage to take risks and trust yourself to make the best decisions.

Finally, Read Your Letter Out Loud
This is the most important step! Once you’ve written your letter, take a few moments to read it out loud. Doing this allows you to really feel the love and appreciation for yourself, and it will help to make your letter even more meaningful. You’ll be amazed at how empowered and motivated you feel after declaring your love for yourself!

Related Reading: Learning To Love Yourself

Day 5: Courageous Bald Dates

Are you ready to shake things up in your dating life? Then it’s time to consider a date with someone who’s bald! Don’t get us wrong; sometimes, it can feel like there are too many factors to consider when finding a match, but hear us out. By going on a date with someone bald, you’ll be allowing yourself to look past the surface level and find out what matters—the person behind the hair.

We know it might feel unconventional, but we promise it will be worth it. Sure, there may be moments when you feel uneasy, but you’ll experience a new type of connection by taking the plunge. Plus, who knows? You may even find yourself surprised by the chemistry you can have with someone bald.

So, here’s to being brave and giving the bald guys a chance! After all, it’s not every day you get to break down barriers and discover what matters.

Day 6: Write What You Want in a Future Partner

Creating a list of qualities and characteristics you want in a future partner may seem daunting. But taking the time to consider thoughtfully what you want and need can save you time and energy in the long run.

Start With the Basics
Before you start writing down a list of qualities, think about the basics. What kind of life do you want to build together? Do you want to travel the world, start a family, or focus on a career? These questions can help you determine what kind of person is best suited to share in these experiences with you.

Make a List of Qualities
Once you’ve established the basics, it’s time to consider the qualities you’d like your future partner to possess. These can range from physical characteristics, like height, build, or hair color, to intangible traits, like kindness, humor, and ambition. Write down anything and everything that comes to mind. You can always narrow down your list later.

Reflect on Your List
Now that you have a list of qualities, it’s important to take a step back and reflect on what you’ve written down. Do any of the qualities seem contradictory? Are there any non-negotiables? Are there any qualities you’d like to add? Taking the time to reflect on your list will help ensure it accurately reflects what you really want and need in a partner.

A Word of Caution
Remember that a checklist of qualities is just the beginning when creating this list. It would help if you also considered each quality’s importance and how it will affect the relationship. No one is perfect, so being flexible and open-minded is important. You may find that the perfect partner has characteristics you didn’t even think to include on your list.

Date 7: Date Yourself

Ditch the dating apps and spice up your evening with a fancy outfit and a good mood. Get dressed up and take yourself out on a date. No matter where you go, take the time to appreciate the little things. Maybe you’ll take yourself out to a romantic dinner or check out a new movie. Or, perhaps you’ll stroll in the park and enjoy the fresh air. Whatever you decide to do, it’s important to remember that you are worth it. So take a break from refreshing your online dating profile and enjoy “me” time. You deserve it!

Day 8: Love Knows No Height

Today, we challenge you to break away from society’s expectations and date someone the same height or shorter than you! Society has taught us that couples should be of similar heights. But why not break away from that idea and give someone shorter than you a chance?

After all, love knows no height. Although your date may be shorter, you could still have a great time together!

Day 9: Transform Your Everyday Look with a Glamorous Makeover!

Take your makeup routine to the next level! A glamorous makeover is a great way to switch up your everyday look and feel amazing! Here are some tips for creating a glamorous look:

Make it Glitter
Glitter is an essential element of any glamorous look! From a subtle glitter eyeshadow to full-on glitter lips, the possibilities are endless. Try adding a bit of shimmer to your lids or even a bold glitter lip for a fun, glamorous look.

Accentuate Those Features
Make sure to highlight your best features! Contour your cheekbones and jawline to define your face, and add a bit of blush to your cheeks for a warm, rosy glow. For your eyes, use a light shade of eyeshadow in the inner corner and a darker shade in the outer corner to create a subtle smoky eye that will draw attention to your eyes.

Go Bold with Your Lashes
Don’t be afraid to go bold with your lashes! If you really want to make your eyes pop, add a few coats of volumizing mascara and a set of dramatic false eyelashes. Or, opt for a pair of lash extensions for a more subtle, yet still glamorous look.

Experiment and Have Fun!
The best part about a glamorous makeover is that you can let your creativity shine! Experiment with different colors and textures and find the look that speaks to you. Have fun with it and don’t be afraid to try something new – you never know what look might become your signature style!

Day 10: Speed Dating

Are you looking for a way to meet people in a fun and exciting way? Then why not try speed dating or virtual speed dating? If you’ve never tried either one, you might be surprised by how much you’ll enjoy it.

Let’s Talk About Speed Dating
Speed dating is where several men and women come together for short conversations with potential matches. Everyone gets a set amount of time to chat with each possible match before they move on to the next one. It’s a great way to get to know someone without making a long-term commitment.

The Benefits of Virtual Speed Dating
Virtual speed dating is an excellent option for those who want to make connections from the comfort and safety of their own homes. It works in much the same way as regular speed dating, but with the added convenience of not having to leave your house. And with the rise of video platforms like Zoom, connecting with potential matches is even easier.

Day 11: Take a Chance on a Stranger!

When was the last time you took a risk? How about taking a chance on someone you don’t even know? Here’s an idea: write your number on a napkin and give it to a stranger you find attractive!

Now, I know this sounds crazy. But we like to think of it as a fun way to take a chance and see what might happen. Who knows, you might even get a smile from the stranger as you walk away!

What Happens Next?
It’s up to you! Maybe you’ll find out the stranger has the same interests as you. Perhaps you’ll find out that you have nothing in common. Whatever the outcome, you will have gained something – the experience of taking a risk on someone you don’t know.

So why not go ahead and take a chance? You never know what might happen!

Day 12: Find Love with a Little Help from Your Friends

Have you ever wished you had a matchmaker to help you find love on a dating app? Now you can! Let your friends take over your dating apps and swipe for you. To make it more daring have them message everyone who matches with you. It’s a great way to get the most out of your online dating experience.

The Benefits of Matchmaking
Your friends know your type and can pick the best matches for you.
You can spend more time getting to know your matches and less time swiping.
You can increase your chances of finding love with a few clicks of a button.

Using a matchmaker can be an effective way to find the right person for you. So why not give it a try? Have your friends take the reins and see what happens. You never know – the love of your life might be just a few clicks away!

Day 13: Go on a Date with Someone Younger Than You!

Dating someone younger than you can be a thrilling and exciting experience that can spice up your love life. It’s an excellent opportunity to experience something new and to open your mind to a different perspective.

Why You Should Try It
You can benefit from a different outlook on life.
You can explore a new and different culture.
You’ll be able to learn something new.
You can enjoy the excitement that comes with a fresh relationship.

FYI: According to a recent study, dating someone younger than you can increase your relationship’s happiness and fulfillment. People who date younger partners tend to have higher self-esteem and more confidence in their relationships.

Day 14: Digging Into the Past

Take 30 minutes to reflect on your past relationships and write down three words that describe them. Were they full of love and laughter, or more of misunderstanding and sadness?

Once you have your three words, take a few moments to imagine if you were to write a book about your past relationships; what would it be called? Write down your title and see what you come up with!

Finding Closure
This exercise is a great way to explore what has been and why it has been. It also helps to provide closure on things that may have been left unresolved.

By doing this, you can better understand who you are and what you have experienced. It can also help you to move forward with a greater understanding and appreciation of yourself and your relationships.

Take the time to reflect on your past relationships and discover what they mean to you.

Day 15: Take a Walk and Make a New Connection

Have you ever wanted to explore your town or city in a new way? How about taking an evening stroll and having a friendly chat with a stranger? It may seem a bit intimidating at first, but the rewards can be great!

Walking is a great way to stretch your legs, get some exercise, and explore your surroundings. It’s also a great chance to meet new people and expand your horizons.

Benefits of a Friendly Chat
Make a new connection – You never know who you might meet, or what kind of interesting conversation you’ll have.
Gain a fresh perspective – Talking to someone new can open your eyes to a different way of looking at the world.
Ease stress – Studies have shown that talking to a stranger can help reduce stress and anxiety.

Remember, it’s just a walk in the park. Don’t be afraid to take a chance and make a new connection. You never know what kind of interesting conversation you’ll have.

Day 16: Write the Things You Don’t Want to in a Partner

It’s easy to get caught up in the excitement of a budding relationship, but it’s important to remember and recognize the things you do not want in a partner. Maybe these are the warning signs that you previously ignored in other partners. Need some help, here were some of mine:

Controlling Behavior
No one should be telling you what to do, how to dress, or who to associate with. If your partner exhibits controlling behavior, it’s a sign that they don’t value your autonomy.

Dishonesty
Honesty is a cornerstone of any relationship. If your partner constantly lies, it’s a sign that they don’t respect your bond.

Negativity
Nobody wants to be around someone who’s constantly negative or critical. If your partner can’t bring positivity to the relationship, it’s a sign that they might not be the one for you.

This list will get you started; take the time and think about the qualities that turned you off or made your previous relationships hard (and avoid those things this time)!

Related Reading: Why You Keep Picking Mr. Wrong

Day 17: A Lingerie Shopping Spree: Treat Yourself!

There’s nothing quite like slipping into a new set of lingerie that makes you feel beautiful, confident, and empowered. So why not make a special night of it? Get yourself the best lingerie you’ve ever seen, and treat yourself to a luxurious shopping spree.

The Benefits of Lingerie Shopping
It’s not just about looking and feeling good! Shopping for lingerie can be a great way to experience something new and exciting and boost your confidence. Plus, who doesn’t love having a few pretty little secrets tucked away in their wardrobe?

How to Make the Most of Your Shopping Spree
Take time to plan your shopping trip. Look online, check out lingerie stores in your area, and create a list of items you’d like to try.
Try something different! Consider pieces you wouldn’t normally go for and add them to your list.
Allow yourself plenty of time to find things that fit and flatter your body.
Be creative and take some risks. Shopping for lingerie is all about expressing your style – and having fun.

So whether you’re looking for something sexy and sultry, fun and playful, or something in between, make sure to take the time to go lingerie shopping. You won’t regret it!

Day 18: Make a Connection with Eye Contact

Making a connection with someone can be as easy as making eye contact. But don’t just glance; hold that eye contact for at least five seconds. To make it even more impactful, give them a little smile. This small gesture can make a big difference.

At first, it may feel a bit awkward to give someone you don’t know a long, lingering gaze. But it doesn’t have to be. Think of it as an opportunity to show appreciation and connect positively with someone. Plus, you get bonus points if you can be the one to break the gaze!

Tips for Making Eye Contact
Be mindful of the other person’s comfort level.
Gently direct your gaze to the other person’s eyes.
Keep your gaze friendly and non-threatening.
Maintain eye contact for at least five seconds.
Break the gaze with a friendly smile.

Eye contact is a simple but powerful way to show someone you like them. Give it a try today and experience the connection for yourself!

Related Reading: Learn How To Flirt In A Way That's Not Awkward

Day 19: Take the Plunge and Go on a Blind Date!

It can be nerve-wracking to go on a blind date, but it can also be a thrilling adventure. You never know what kind of connection you’ll make or where it might take you. A blind date is a chance to break out of your comfort zone and explore something new.

Why Blind Dates Are Worth Trying
If you’re looking for a fresh start, a blind date can be a great way to meet someone new. After all, why not take a chance? You never know who you’ll meet or how it could change your life. Here are just a few of the potential benefits of going on a blind date:

• You can get out of your comfort zone. Blind dates offer the opportunity to experience something new and exciting. Even if you don’t end up hitting it off, you can still make a new friend or learn something about yourself.

• You can explore unfamiliar places. Blind dates often take place in new places you wouldn’t usually visit. This can be a great way to explore more of your city and find hidden gems you never knew existed.

• You can open yourself up to new possibilities. From talking to someone you otherwise wouldn’t have met to discovering a new restaurant, blind dates can open up a world of possibilities.

Day 20: Attend a Meetup Group

Living in a city can be overwhelming, especially for singles looking for love. Luckily, plenty of meetups in the US that help make meeting new people more accessible and more enjoyable. Whether you join a meetup related to your interests or try something completely new, you can expand your social network and discover new passions.

Make the Most of Every Meetup
Going to a meetup is a great way to start a new chapter of your life. Not only can you meet potential partners, but you can also make new friends and explore exciting activities. Research has even shown that living and loving your life increases your chances of attracting people to you. So, why not take the plunge and attend a meetup every week?

• Discover new hobbies and passions

• Make new friends and deepen social connections

• Meet potential partners in an informal setting

With so many meetup groups, there’s no reason not to take advantage of this opportunity to meet new people, make connections, and try new activities. Who knows, you might find the partner of your dreams!

Day 21: Identify & Show Yourself Love Via Your Love Language

We all know that feeling of being drained and exhausted from life yet having no idea how to make ourselves feel better. To find the answer, try looking inward! Knowing your love language is the key to unlocking the secret of self-love.

Take the quiz. There’s a great quiz you can take on Chapman’s website to figure out which love language speaks to you.

Once you’ve identified your love language, it’s time to show yourself some love! Pick one thing you can do to show yourself love in that language. It could be as simple as taking a few minutes to write something positive about yourself or setting aside time for a relaxing massage. By taking the time to understand your love language, you can begin to show yourself the love and care you deserve. And don’t forget: self-love is the key to a happy, healthy life!

Day 22: Unlock the Secrets of a Lasting Marriage

Ready to learn the secrets of a successful and lasting marriage? Take a cue from the couple you admire, and go on a date with them! This is an excellent opportunity to observe how they interact and to learn from their years of experience together. Listen closely to their conversations and ask questions about their journey as a married couple. You may be surprised to discover the key to a long-lasting relationship!

Gain Insight Into a Lasting Marriage
Observe how the couple interacts and engages with each other
Listen to their conversations and ask questions
Learn the secrets of their successful marriage
Discover how they met and the journey of their relationship

Make the most of this opportunity to learn from the best!

Day 23: Avoid the Social Media Vortex

Are you getting sucked into the social media vortex? We all know it can be hard to step away from our phones and laptops–especially when there’s so much exciting content to explore. To help you keep your social media use in check, here’s a simple rule of thumb: Stick to a maximum of 10 minutes on social media today. That’s enough time to explore the latest news, catch up with friends, or just scroll through your feed.

Day 24: The Setup

Here is an exciting solution that could bring you one step closer to finding that special someone! You could find your person by asking your friends to set you up with one of their single friends.

Here are a few reasons why you should give this a try:
You already have a mutual connection
Your friend can vouch for their character
You already have common interests
You could save yourself time and effort

By getting to know one of your friend’s single friends, you could be entering a world of endless possibilities. Don’t worry; your friend will know if you two will hit it off and will be more than happy to be the one to introduce you!

Day 25: Treat Yourself to the Ultimate Pamper Night

Let’s face it; life can get hectic. So why not take some time and indulge in a luxurious, pamper night? Put your feet up, relax, and enjoy a soothing routine that will have you feeling refreshed and rejuvenated. Here’s one of my favorite pamper routines.

Day 26: A Date With a Difference

Forget dinner and a movie – why not try something a little different on your next date? Why not try a sporting date? From badminton to golf, tennis to baseball, there’s something to suit all interests.

And even if you’re already a pro, you can still get your date to teach you the game’s finer points. Not only will they feel flattered that you asked for their help, but you can spend quality time together.

Benefits of a Sporting Date
A chance to bond with your date in a relaxed environment
Fun and exciting activities to keep you both entertained
You can show off your competitive side
A chance to show off a new skill

So, why not ditch the traditional date night and try something different?

Day 27: Say Goodbye to Flings, Exes, and Friends with Benefits

Having a clean contact list can provide a sense of control and organization in our lives. But beyond the apparent contacts like family, colleagues, and close friends, removing the flings, exes, and friends with benefits from your phone contacts is important.

Why You Should Delete Flings and Exes from Your Phone Contacts
Letting the list of contacts in your phone get out of hand is easy. But before you know it, you’re scrolling through your contacts and seeing many people you’d rather forget. This can lead to unwanted reminders of past relationships, bringing up old emotions and causing anxiety. Removing the flings, exes, and friends with benefits from your contacts can help you avoid those situations.

Once you’ve completed deleting the flings, exes, and friends with benefits from your contacts list, you can start fresh with a clean slate. Reminders of past relationships no longer bombard you; you can focus on the future relationships that matter now.

Related Reading: The Pros & Cons Of Casual Dating

Day 28: The Truth Will Set You Free

We all need a little help now and then. Ever wonder why you’re still single? Why not ask your most truthful friend why. But don’t just settle for a surface-level answer; encourage them to be honest and straightforward with you, no matter how difficult it might be to hear. Taking a step back and looking at your romantic life with another set of eyes could be the key to unlocking the answer you’ve been looking for.

The Benefits of Being Honest
Opening yourself up to the honest opinions of your friends can be daunting, but the benefits can be immense. A true friend will tell you the truth, even if it’s difficult to hear. Their feedback could help you identify patterns you hadn’t noticed before or provide a different perspective on the situation. And above all else, it can help you to make more informed decisions about your romantic life in the future.

Day 29: The Art of Spontaneity: Seize the Dating Moment

Dating can be a long, arduous process of getting to know someone. But if you’ve just matched with someone you think you could click with, why wait? Seize the moment and go out within 48 hours of matching with someone.

This is all about spontaneity and taking that leap of faith. You know when you just have a good feeling about someone and want to act on it? That’s when you should go on a date (safely and responsibly, of course!).

A spontaneous date can be a thrilling, exciting experience. It can also be a great way to get to know someone faster. When you’re feeling the chemistry, why wait? The best moments in life are often the most spontaneous ones, and this is no exception.

Day 30: Reflection

After taking on the challenge of dating for 30 days, reflecting on the lessons learned is important. It’s an opportunity to gain insight into our own lives and personalities. Here are some reflection questions to consider:

• What did I learn about myself? Did I discover any new strengths or weaknesses? Do I better understand who I am and what I want?

• What did I like? What elements of the challenge did I enjoy the most? Was it meeting new people or taking a risk by trying something new?

• What did I not like? How did I handle the uncomfortable moments? Did I embrace the challenge or shy away?

• What days did I feel uncomfortable? Were there any days I felt anxious or out of my comfort zone?

• What days did I love? What was the highlight of my dating challenge?

Reflecting on these questions can help us gain insight into our own behavior and allow us to make positive changes in the future.

Congratulations On Completing The Dating Challenge!

You just completed something scary and challenging, probably pushing you outside your comfort zone. That deserves a celebration!

You Should Be Proud of Yourself
Your efforts were not in vain. You took on our dating challenge, and completed it. You should be proud of yourself!

Let Us Know How It Went
We would love to hear about your 30-day dating challenge journey. Leave a comment below letting us know your favorite days, or tag us on social media. Share your stories and experiences with us!