How to Stay Positive and Happy While Dating in Your 40s

You might believe that if you’re dating in your 40s, the only guys left are rejects with a shit ton of baggage.

I think this belief is rooted in the simple truth that once you hit your 40s, any man in the dating pool is likely divorced with children. And that man is probably carrying around residual scars from his divorce.

A bag on the floor,  illustrating the baggage that can come with dating in your 40s

What I want you to know is that these factors do not make someone undateable. In fact, I would guess that if you’re dating in your 40s, you might be in a similar situation.

During my 20+ years as a coach and therapist, I’ve heard many women say, “Everyone on dating apps is horrible, sketchy, unattractive!”

I have to remind them, “But you’re also on the dating apps. Are you including yourself in the ‘everyone’? Or is it just ‘everyone else’?”

Don’t be too quick to make assumptions about someone else’s story.

Dating in your 40s and beyond can be extremely challenging, but it’s not impossible.

So many people find love later in life. You can totally have a second (or third or fourth) act. Let’s talk through how to stay positive and happy while you search for it!

Post it notes on a wall depicting reevaluating while dating in your 40s.

Reevaluate your dating criteria while dating in your 40s

Do you have a dating wish list? Maybe you think back and remember your high school boyfriend fondly: he had a full head of hair, sparkling teeth, played the guitar and swept you off your feet.

Now, you’re looking at profile pictures of a lot of guys with thinning hairlines, wrinkly skin and dad bods.

Please remind yourself that looks are not the most important thing when choosing a partner. Seriously.

As for the “baggage” that these guys might be carrying, reminder: everyone has baggage! And the older one gets, the more bags they likely have. Please don’t use “baggage” as an automatic reason to rule someone out. There are degrees of baggage and you should evaluate potential dates on a case by case basis.

If a guy is willing to share his history with you and you see evidence that he can be introspective and that he has the ability to take responsibility for his actions and mistakes, that’s a huge green flag—a sign that he might make a great partner despite any mistakes he may have made in past relationships.

With any luck, we all learn and grow as we move forward in life. If you’re struggling with dating in your 40s, now is a great time to put pen to paper; to make a list of the five most important qualities you want to have in a partner. Your list (hopefully) includes things such as:

  • Honesty

  • Showing respect

  • Willing to communicate and compromise

  • Self-control

  • Understanding

  • Kindness

Everything else is negotiable! Be clear about what your must haves are and be willing to be flexible on some of the less crucial stuff. And your spirit just might remain intact on your dating journey!

A woman in a bubble bath showing how to stay positive and happy.

How to stay positive and happy? Take care of yourself!

Getting discouraged on this journey is inevitable. You will have challenges along the way. You may kiss a few frogs. Maybe more than a few. Instead of seeing those challenges as proof that you should just get out of the dating game, I encourage you to make a plan to deal with the challenges that will undoubtedly arise. And I encourage you to be incredibly kind to yourself throughout this process by making time for self care. This is the fun part.

If dating hasn’t been going well, it’s perfectly acceptable to take a step back and focus on yourself for a day, a week, or longer.

During that time, you can reevaluate your list of must haves and dealbreakers. You can also unplug from dating altogether for a while and do things you love to do that have nothing to do with meeting a man. Go out with friends, watch your favorite movie (again and again if that’s your thing), go for a walk, treat yourself to a nice meal, or even to the overdone-yet-so-so-satisfying-stereotypical bubble bath or spa day. It’s cliche and cheesy and wonderful.

I would recommend that even if you do decide to jump back into the dating pool, keep up with self care, whatever that self care looks like for you. Whether part of a couple or a free agent, taking care of yourself must be at the tippy top of your list.

If you’re reading this article, dating is probably important to you but don’t let it be the only thing that’s important to you!

Two women sit with hands clasped discussing dating in your 40s

Ask for help for dating in your 40s

I’ve said it many times throughout this blog post and throughout my long career working with women: dating is hard; online dating is hard; and online dating in your 40s is really really hard.

It’s not too late for you and if you’re struggling I would love to help you! I have created a group coaching program to help you learn to date strategically and find a good fit partner —no matter your age! Learn more below, and sign up to join me!

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