Fall is in full swing, cuffing season is here, and Thanksgiving is just around the corner. Whether you’re navigating long-distance connections, staying safe while online dating, or figuring out how to take your dating game to the next level, this week’s Dear Damona episode has you covered.

We’re dedicating the whole show to your most pressing dating dilemmas and relationship questions as we head into the holiday season. From timing intimacy to challenging gender roles, we’re diving deep into the questions that matter most to you.

(00:25) Dear Damona 

Do you have questions? Damona has the answers! Submit your dating and relationship questions on Instagram, TikTok, or Facebook, or leave a voicemail or text to 424-246-6255, and hear Damona’s answers in a future episode!

Love Beyond Borders (1:43)

Adrian’s dating app experience has been surprisingly wonderful – except for one geographic challenge that keeps getting in the way. 

“Dating sites in the last two years have been wonderful – I’ve made friends, had exciting dates, and even a relationship for a couple of years. The dilemma for me has been my location and the willingness of men to travel. I’m willing to travel to meet them, but of course, that can be tricky. Is there a specific dating site that I should use for this situation?”

When Digital Footprints Fade (10:55)

Sue’s dating detective work uncovered something fishy – between mysteriously disappearing profiles and stories that don’t quite add up, she’s stumbled into a digital dating mystery that’ll make you think twice about your next match. 

She asks: “Dear Damona, recently it seems that a few of the men I’ve met online dating on Bumble have removed their online profiles as soon as we share phone numbers. Do you have any data or insights about this behavior?” Sue shares concerning details about mismatched accents and overlapping life stories between matches that raised red flags.

The Perfect Moment (18:47)

When it comes to intimacy, timing is everything. But who decides when the clock strikes “right”?

This listener’s bedroom boundaries bring up the age-old question of when to take things to the next level.

Our anonymous listener asked, “Do you have a recommendation for when two people who have started dating can sleep together? Or what to say if my date proposes we sleep together and I feel it’s too soon?”

Rewriting the Dating Rulebook (24:39)

Ladies first? More like ladies waiting! 

Why are women still sitting around waiting for men to make the first move? Time to shake up those dusty dating rulebooks! 

Erin writes: “Do you know of any couples or of any relationships in which the woman asked the man out, or the woman was the initiator? It’s a follow-up to the point where you have encouraged women to ask men out. Some people like to think that the world is slowly changing; however, at the same time, a part of me doubts it, as in I just see it as men always being stuck with that gender role.”