The questions have been pouring in and so we are doing an all-Dear Damona episode of Dates & Mates today! Time to ease your minds and get you back on track for love in the new year.

In case you’re new here, our podcast episodes typically happen in three parts – headlines of the week, interviews, and a Dear Damona Q&A segment but we love shaking things up! It’s always to help you understand yourself and handle the ups and downs of modern dating.

“F THE FAIRY TALE” GIVEAWAY (0:00)

If that resonates, be sure to pick up a copy of Damona’s new book, F the Fairy Tale, out January 2nd! Enter our pre-order giveaway at DamonaHoffman.com/giveaway for a chance to win two VIP tickets to The Drew Barrymore Show, a $500 travel voucher, and a $500 shopping spree at Democracy Clothing. 

Now…let’s get to these questions!

Dear Damona (3:22)

03:27 IG DM from Aaron

Hi Damona, I started dating someone just under two months ago. It’s going well; the conversation flows. I feel secure and calm when we are together. He told me he loves me a little over a month in. Is that too fast? I’m pretty inexperienced with long-term relationships. How should I know when to say “I love you”?

7:02 Voice memo from V

Hi, Damona. I’m a big fan of your show. Thank you for everything that you do. It’s been so helpful. I do have a question. I’m wondering if you have advice for the ladies out there who are the ones being engaging, keeping a conversation going, asking the questions, and doing the heavy lifting because it’s getting tiring. I find myself in this position. It’s frustrating that it feels like a lot of guys I match with don’t know how to pass that ball back and forth in a conversation. It feels like a dead end. And, frankly, I’m feeling so over it. So, I would love to know your thoughts on if I should just move on

15:57 Email from Montie

Dear Damona, I hope you know that you are my bestie (in my head)!!! You’ve always given such great advice; sister don’t fail me now; just shoot me straight! I’ve been divorced for 12 years, and while I’ve had a couple of significant relationships, nothing has ever stuck as my forever relationship. I’m currently seeing someone who is much younger (I’m 57; he’s 39…gulp!). We click, we vibe, and the relationship is relaxed and easy. We are monogamous, and he’s wanting a forever future with me (we’re approaching 4 months together). I adore him, but I often wonder if I’m excited about being off the market finally or if we really will fit long term! Help!! Or realize that this could just be one of my deal breakers? Honestly, the thought of dealing with it stresses me out.

 

21:48 DM Voice Memo from C:

Dear Damona, I’ve mentioned before that I’m dating in my 30s. And, you know, it’s a priority for me to have a family. I’ve been going on lots of dates. But yeah, I just have not found, honestly, anyone that I’ve been really excited about. There hasn’t really been any man who I’ve gone on more than four dates with. And, yeah, I mean, look, I have to say it’s always me who’s ending it. I’m really struggling, in all honesty, in finding men who are emotionally mature. Just what I consider a basic level of maturity is just so difficult to find for some reason. And so, and I think that’s partially contributing to my disillusionment. But yeah, if you have any tips for sourcing men who are more emotionally mature, that would be great. I’m open to it in real life. I’m open to online. I must be just looking in the wrong places. I don’t know. Thanks!!!

Have More Questions? (33:37)

Submit your questions on Instagram, X, TikTok or Facebook and hear our answers live on the show!