Dating While Gray & The Later Daters

“Is finding love different at every age?” With shows like The Golden Bachelor and Later Daters dominating our screens, there’s a new interest in seeing the dating lives of older daters explored on TV. 

But as Laura Stassi, host of Dating While Gray, reveals in this week’s episode, many of our dating challenges and solutions remain the same, regardless of age, gender, or sexuality. 

Get ready for an insightful discussion about modern dating that challenges conventional wisdom, plus stay tuned for a special Dear Damona segment where Laura joins Damona to answer listener questions about long-distance dating possibilities and navigating intimacy challenges.

(2:19) From Heartbreak to Dating Superstar: Meet Laura Stassi

You won’t believe how Laura turned her own “gray divorce” into a mission to help thousands find love again. 

After a 30-year marriage ended, she didn’t just bounce back – she revolutionized the conversation about dating after 50. 

Now her podcast Dating While Gray connects with thousands of listeners worldwide, proving it’s never too late for a fresh start in love.

Love Has No Age Limit (6:21) 

Think dating at 25 is totally different from dating at 65? 

Laura and Damona bust this myth wide open, revealing how our core desires for connection stay remarkably constant throughout our lives. 

They explore why being older actually gives you some serious advantages in the dating game and how life experience can make you a better partner than ever before.

The Secret Spots Where Love is Hiding (14:04) 

Forget swiping right – Laura shares her genius strategies for meeting potential partners in places you’d never expect. 

From high school reunions to neighborhood barbecues, she’s got the scoop on where real connections happen naturally. 

You’ll be shocked by her stories of couples who found love in the most surprising places and get actionable tips for expanding your own dating pool beyond the apps.

Dating Rules: Keep ‘Em or Trash ‘Em? (21:53) 

Should men still pay on the first date? Is it okay to text first?

What about waiting three days to call? Laura and Damona dive deep into which dating rules are ready for retirement and which timeless traditions actually help build stronger connections. (Their answers may surprise you!)

Get ready for a fresh take on modern dating etiquette that works for any age.

Connect with Laura:

Podcast: Dating While Gray

Instagram: @datingwhilegray

(30:57) Dear Damona & Laura

Ever wondered about starting a long-distance relationship before moving to a new city? Or how to date confidently when dealing with health issues? 

Question from an Anonymous Listener:

Dear Damona, I just turned 70 years old, and I’m in good health. Still working full-time. 24 years ago, the man I was married to at the time transferred us to California. 

I was originally born and raised in Louisiana, and I’m a Southern girl through and through. 12 years ago, I divorced my husband, and I long to go back to the South. I have a daughter who lives in Tennessee, and my desire is to move there and find a lovely southern gentleman and settle down. 

I did try dating sites for a while here in California, but I would prefer to be in the South. I want to go on a dating site in Tennessee, but I’m not sure how that would work. Long distance or even how to go about that? Frequent commuting, of course, is out of the question, and I’m wondering if you think it’s even a good idea to try to look into relationships long distance until the time that I can move there, perhaps in about a year.

Question from a listener named Jenny: 

I am having an awful dating self-esteem issue, and I know that this particular problem is highly common among women. 

You see, after having three kids who are now 27, 25, and 22, and after being a teacher for 30 years, my bladder has taken a huge turn for the worse. Here I sit at 55 years old, feeling like an elderly person in poise pads. The incontinence has gotten out of hand. I’ve had surgery and physical therapy to fix the problem with no luck. 

I am so sick and tired of people making jokes about others needing adult diapers because it is a real problem that keeps me from doing anything that will prevent me from being near a bathroom, as I have to go every hour. And all of these jokes make me feel like I am unsexy and that no man would ever want me. What am I supposed to do with this problem?

Do you have questions? Damona has the answers! Don’t forget you can submit your dating and relationship questions for our Dear Damona segment on Instagram, TikTok, or Facebook, or leave us a voicemail or text to 424-246-6255, and hear Damona’s answers live in a future episode!