There’s been A LOT of talk this year about dating burnout and swipe fatigue. And while we know that the frustration is real, the ultimate takeaway is people are STILL dating or else they wouldn’t have the experiences to complain about. 

So what if we reframe our dating troubles and see them as learning opportunities? What dating doors might open for you then? What power could you snatch back from the jaws of dating apps, or ghosting, or other forms of fatigue or burnout?It’s time to hop back in the driver’s seat of your dating life and that’s exactly why we’re serving up an extra-special “all Dear Damona” episode today!

Dear Damona (2:25)

3:00 Text from A

Is it generally a good idea not to message someone on the app if the last message was sent by me, meaning it’s now his move? I matched with someone last weekend. He expressed that he was extremely interested in getting to know me and that I seemed to have the strong character he’s looking for in a partner.

Side note: I don’t have a bio written yet. I’m new to this, and yes, I will put up a bio soon. So he was making this call, but my strength of character was purely on my photos, basic info, and interests. I thanked him for the compliment, then directly asked him, with so little to go on, what had given him a sense of my character; he explained that having practiced medicine for so many years, he learned to read people and look for cues that others might not see. He’s not wrong. I am all those things. But let’s just say I was cautiously impressed but also suspicious by his observations. I asked him a little about his work, which he answered without hesitation. And then, after my last two messages, which confirmed what he’d explained, he didn’t message back. That was three days ago. Should I assume that this thing has already fallen flat on its face? Before we even had a chance to meet? My friend told me to wait, and he probably gets hit on by a million nurses, so I should be the cool one.

11:53 Email from Gary

Hi, Damona, I enjoyed your conversation on NPR. I started dating after healing from a relationship, but I struggle to manage and set expectations for potential partners. Could you please shed some light on this scenario and provide advice?

17:13 Instagram DM from Vernee

Dear Damona, I’m curious about dating up. I have habitually dated men who made less than me because it didn’t matter to me, and often, in these relationships, I found myself taking care of them in ways that they could not reciprocate.

Anyway, I’m fresh off of a breakup. Oof! Long story. Incoming. But the week before the breakup, my ex-boyfriend asked me how much money I made. He had previously told me what he had made a few times, and I never felt the need to share, but we had plans to move in together, so I didn’t see the harm at this point. I told him how much I make. He seemed a bit surprised, and he said, “Oh, you make comfortably more than me.” I said, yes, I do. I think it’s possible that he felt some type of way about that from an ego standpoint. Many men still carry that provider thing, and I’d like to be taken out sometimes or suggest places where we can split the bill or buy our own tickets to a nice event. I’m not asking to be spoiled, and I believe in sharing costs, but what can we do when they make less than you and have poor money management? My ex would pay for some of our meals out, but I’m pretty sure most of that went onto credit cards that his parents would pay for.

And then, after a year together, my ex told me that he wasn’t in love with me, even though all of his behavior said otherwise. So I told him goodbye. I know I’m not the only woman to go through this. My heart can’t handle any more fixer-upper men. Where did all the grown men go? So many of us are stuck with Peter Pan on one level or another.

27:50 Text from Tasha

Dear Damona, I love your story. I just recently discovered your podcast. Have you helped many singles in their 50s? I am 54 and just really am wondering if it’s too late. Isn’t it more difficult to find love after 50?

Send Us YOUR Questions (33:04)

Don’t be shy! If you’ve got a burning question about love, dating, or relationships! You can reach out on Instagram, TikTok, or Facebook, or even give us a ring or text us at 424-246-6255. We absolutely adore hearing your voices, so don’t hold back! Whether it’s a whisper or a shout, your input help us tailor the best dating advice for you. Drop us a voicemail or slide into our DMs with a voice memo – we can’t wait to hear from you!

Keep Listening!

If you enjoyed this all Dear Damona episode, you would really like our recent episode with the host of the “I Thought it Was Just Me” podcast, Lane Moore: Tinder Love & Love Don’t Cost a Thing