Dating in Your 40s: Do a Dating Challenge!

Dating is fun.

Dating is hard.

Dating is overwhelming and scary, especially when you’re in your 40s, and you’re hitting the dating scene again.

Let’s face’re not a pimply teenager wearing rose colored glasses.

You’re a sometimes pimply, gravity challenged, 40+ woman wearing battle scars from your past forays into love.

But, despite that cold hard reality, you’re optimistic and want to believe love is out there for you (it is!).

The idea of dating to find it, however, sometimes sounds like more trouble than it’s worth.

I know all of this because I’ve been there myself!  I got back out there on the dating scene last year after a hiatus following the ending of a long-term relationship.

I know the butterflies and the doubt.  I know the silent prayers before a date: " creepy vibe, roving hands, or my future stalker." (I have an irrational fear of attracting a stalker!)

Yes, I ultimately wanted to find an amazing man for a relationship, but I’ve never been interested in the casual dating scene.  

I have nothing against casual dating, but it’s just not where I shine.

So, to make it fun for myself and to take the pressure off the entire process, I decided to try a dating challenge!

My mission...go on ten first dates within a three month period.

Spoiler alert...I didn’t finish my challenge.

That’s not because I gave up!  But it was because I found an amazing man on one of those dates and six months later, we’re still together.



Before we get into the ‘why' let’s quickly talk about what is a dating challenge.

A dating challenge can be anything you decide to try that’s pushing you beyond your normal limits.  With that said, you should never do anything that doesn’t sit well with you!  That’s not the objective.  It’s figuring out where you tend to take the easy road and riding that edge.

For me, since I’m not typically a casual dater, I opted for a challenge around a certain number of first dates.

While you can certainly come up with your own creative challenge, let’s explore that particular challenge (just in case you're interested in giving it a try!).

I want you to challenge yourself to go on X number of first dates within a particular window of time with the sole mission of just dating (I’ll let you fill in the specifics on how many dates and in what time frame you want to complete it). Three months may be more than enough time and you want to tighten it up to six weeks, or ten dates may be too many for you (or not enough!).  The point isn't the specifics it's that you're actually doing something you don't typically do.


What are the benefits of a Dating Challenge?

There are always benefits to pushing yourself beyond your comfortable edge.  When it comes to dating, challenging yourself gives you many advantages:

It takes the pressure off - Instead of interviewing a first date to see if they’re future husband material, you get to simply enjoy the moment for what it is which makes it a lot less stressful! A first date does not mean an instant relationship!

It’s fun - Even for someone like me that doesn’t enjoy casual dating, meeting up with a cute guy that, at least for the duration of the date, seems interested in you, all while flirting with each other is fun!  What’s not to love about that?

You do something you don’t typically do - You get to decide your hard stops when it comes to doing things you don’t typically do.  But since most people err on the side of extreme caution, that creates a lot of opportunities to explore new areas that won’t bump up against any boundaries.  Doing this allows you to grow and face fears, which makes you stronger and more confident.

It helps you practice - This applies in particular if you’re back on the dating scene after being off the market for a long time.  Even if you’ve been dating for awhile and you want to take a new approach, it will help you practice.  It gives you a chance to see what’s out there, to get comfortable being uncomfortable, to hone your flirting skills, and see yourself as desirable through someone else’s eyes.

You might just meet someone amazing - Here’s what's ironic about not looking at each perspective date as future boyfriend/husband material.  When you are focused on the right now, and you show up in the moment, it makes you more real and more confident.

From talking with guys on this, that makes you super sexy and desirable.  By dating more people than you typically would, this opens you up to connect with someone you wouldn’t have otherwise.

You move past the bad dates more easily - If you're out there dating, you will inevitably go on bad dates.  It's part of the process. When you're trying to find a boyfriend, a bad date can feel deflating because it's one step further away from your goal.

But, when you are only challenging yourself to go on X number of first dates, a bad date is still a successful date! You release the personal attachment to the outcome.  You also know more dates are on their way, so a bad one allows you to enjoy the good ones that much more.



Technically, there are no rules.  You get to make the rules.

But, there are a few best practices to keep in mind.

Get clear on your objective - My mission was ten first dates.  That didn’t mean I couldn’t go on second dates if asked and I wanted to go, but for me to complete the challenge, I wanted ten different guys for the first dates.

By getting crystal clear on what you’re trying to achieve and why it'll help you stick with it to the end.  In other words, what’s in it for you?  

Decide on your boundaries for intimacy - For me, the challenge wasn’t about sex.  While there’s nothing wrong with sex on a first date, it’s not me, so that was not in my plans (nor did it happen!).  But, for you, you may be okay with that, and if so, go for it!  But, if that’s not you, then stick to your boundaries and don’t go there.

Don’t worry about whether they like you - The goal is for you to get in the mindset of figuring out whether you like them, so don’t worry too much about whether they like you.  Other than acting like a total loon, you can’t control whether someone else likes you anyway.

When you stop thinking about yourself, you’ll focus on him, and that’s exactly where your focus should be.  You are trying to get to know him after all!

Don’t worry about getting a second date - Your mission for this challenge is to get first dates so don’t worry about whether he’s going to ask you for a second date.  If he does and you want to go, great!  Say yes and have fun!  But, don’t let that distract you during your first date.  Remember, it’s one step at a time.

Have fun with it - To keep it fun and somewhat lighthearted, I made a page with ten hearts on it to check off after each first date.  Simple and probably cheesy, but it helped me to remember not take it too seriously (and it made my end goal very visible)!

Give yourself permission to change the rules - Maybe you realize you need to tweak the challenge as you go along...that’s perfectly fine!  Maybe ten dates are too many, or three months isn’t quite long enough.  There’s no right or wrong here; it’s your challenge so make it work for you, not against you.

It’s okay to call off the challenge - Maybe you meet someone amazing, and you hit it off and start dating this person exclusively (that’s what happened to me!), or maybe you made the challenge too long, and you’re not getting anything from it anymore.

It’s perfectly fine not to finish your challenge.  But, word of warning...if you are calling it off because you met someone you want to date exclusively, be self-aware enough to realize if it’s because you truly like this person or you’re just grabbing the first guy that shows interest in you.



A dating challenge can be a lot of fun if you go in with the right mindset.  It can jumpstart your dating and help you show up confidently (guys can sniff out desperation and someone looking for an insta-boyfriend will definitely give off that vibe).

By not thinking beyond that first date, you’re also more present in the date and able to have more fun.

The beautiful result of all of’ll be irresistible to the men you go out with because men love confident women that are secure in their lives.

So...I have to ask...what’s your dating challenge going to be?