When Dating Gets Harder with Age

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Hey Wendy,

I’ve fallen in love with my friends for YEARS.

My favorite feelings are apparently safety and comfort…which means dating gets harder and harder.

I try to get myself into a queen’s headspace (taking a bath, etc. beforehand) but I am finding it harder and harder to commit to actual dates. I’d rather chill with the guy I know, even though he’s already told me he’s not interested in me that way. It seems to get harder as I get older. Please help!

Karen P.


Hey Karen,

There are only three things you need to do to succeed at dating to find your love:

1. Start dating.

2. Don’t settle.

3. Don’t stop.

That’s it. That’s the magic to meeting a great partner. Your life could change in an instant when you find the right person for you, and you can only get there by doing those three things, in order.


I think the thing that’s tripping you up is you think dating is the point.

And dating is uncomfortable.

And there’s a big bag of bullshit you have to muck through that often accompanies the dating process.

I get it: Most of the time, you just don’t want to. You just don’t feel like it. It’s effort. It’s exhausting. It can feel like it doesn’t pay off.

This sounds a lot like me talking about not wanting to hit the gym, right?

There are a lot of us who don’t super-love to exercise. But getting that cardio in — while inconvenient, sometimes unpleasant, and often uninspiring — is for the benefit of our overall health and pays off big time in the long run.

Like regular cardio, dating isn’t done just for kicks. Dating isn’t for the “fun” of dates themselves — that’s not the point. It’s done for the bigger picture, for your overall satisfaction in partnership.


Now, am I saying all single people can’t be happy and feel loved? Hell. No!

Single is a totally solid choice that I respect and can get behind.

Some of us are completely satisfied single.

I know some amazing women who think the most satisfying, best fit for their lives is to have their number-one, top-priority partner be themselves. (It’s called Solo Poly.) This is awesome only if you decide it’s awesome for you.

Maybe hanging out (and snuggling up) with your friend, getting what you need emotionally from your community, and being true to yourself is the right path for you. You can be single, and comfortable, and loved by your people and yourself, and be happy. If that fits for you, then voila, you’ve arrived!

If being happy and single doesn’t feel like an authentic expression for your life — if you feel underutilized and unfulfilled without a partner — then that’s not your path, and you’re gonna have to get out of your comfort zone and go to the gym…um, I mean hit the dating field.


I wish I could give you a “go on four dates, and the fourth one will be your person” soundbite, but Karen, we don’t know when it’s going to happen for you. I can say with confidence that it won’t happen if you do nothing.

Your odds of it all coming together for you will improve immensely if you’re in good working order and know how to be a great first date yourself. Being a great first date also has the added bonus of making the overall process more fun. If you want all the details on how to set yourself up to have more enjoyable and successful dates, pick up , or at least watch my little video. But I am going to leave you with three key points now:


#1. Watch the stories you tell yourself. Common lies we tell ourselves are:

  • “I’m too old and it’s too late for me.”
  • “I am too much, no one can handle all of who I am.”
  • “I’m too ___!”
  • “I’m not enough of ___!”

None of it is true. And these disempowering thoughts get in your way of wanting to leave your comfortable couch. These lies and stories I’m referring to also include all the recapping of dates your inner critic is bound to do. She’ll tell you all the ways you blew it. When you notice you’ve created a new, disempowering story, be gentle with yourself and simply say, “Nope, not true. What else you got?”

#2. Don’t spend too much time in the screening (back and forth) process. Get to that coffee shop close to your house (so you’re not too inconvenienced) and meet face to face. Remember the game “telephone” when we were kids? There’s a reason things get all garbled up when we’re just communicating through text and phone calls. It’s actually a bigger time-waster when we’re trying to vet. If you like what he wrote on his profile, meet up!

#3. Get a dating buddy — someone you can talk to about your dates and who can help brush you off from the bad ones. If you don’t have anyone, 


“It only takes one moment on a first date for my whole life to change forever.”

Good luck and enjoy!

. . . .

Wendy Newman is the author of . She’s a dating, sex, and relationship expert who’s led hundreds of workshops and revolutionized the lives of over 70,000+ women internationally.

You can send a question to the column via email: Wendy@WendySpeaks.com