Have you ever wondered what 18 years of marriage really looks like?

Not the Instagram highlight reel, but the thousands of conversations, quiet compromises, and inside jokes that only come from choosing each other every single day?

This week on Dates & Mates, Damona does something she’s never done before. In honor of her 18th wedding anniversary (yes, 6,500+ days of love and lessons!), Damona is joined by her husband Seth on the mic to co-host an entire episode of Dear Damona where the couple tag-teams your biggest dating and relationship dilemmas.

From dating app anxiety to long-term communication ruts, they bring advice straight from the front lines of a real, evolving partnership. Seth may be a behind-the-scenes guy (TV writer, Virgo, very anti-social media), but he brings thoughtful insight and a few surprises too.

 

(6:03) When the Peanut Gallery Gets Too Loud

“I feel like I’m constantly second-guessing my own judgment…”

The first question comes from Bella, who’s 24 and feeling overwhelmed by unsolicited opinions, from friends and Facebook groups. When everyone’s got something to say about who you’re dating, how do you know what to take seriously and when to trust your gut?

Damona and Seth unpack the difference between a red flag and a rumor, and reflect on how the dating landscape today is more crowded with outside voices than ever before.

(14:38) Singles Events Are My Nightmare

“I freeze. I feel awkward… I end up standing on the sidelines.”

Shawn wants to show up intentionally and find real-life connection, but every time he gets to a singles event, anxiety shuts him down. Sound familiar?

Seth shares a psychological trick that helped him overcome social anxiety back in his single days. Damona adds her signature PS World technique (plus a few ice cream-based openers that actually work).

(25:24) Am I Talking or Just Repeating Myself?

“It feels like my partner isn’t truly listening anymore.”

Beth has been with her partner for several years but feels like she’s hitting a communication wall.

Damona and Seth talk about how to reset connection, why “invisible conversations” happen more than we realize, and how therapy doesn’t have to mean something is broken; it can be a tool for growth.

(35:55) Help! My Friends Are Dating Cynics

“Every time dating comes up, the conversation turns negative.”

Jill is trying to stay hopeful about love, but her friend group is stuck in a doom spiral.

Damona explains why protecting your dating mindset is crucial (and sometimes means snoozing the group chat), while Seth adds perspective on why some people stay stuck in dating cynicism.

💌 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!