First dates are gateways to new possibilities, blending excitement and apprehension. 

They offer a unique chance to make a lasting impression, showcase your true self, and gauge compatibility with someone new. More than just an outing, first dates set the stage for potential relationships and define the path of your dating journey. No pressure…right?

Luckily for you, we’ve got dating coach Mat Boggs to guide you through first-date essentials—from spotting red flags to conversation tips and time investment. Mat will help you learn to release that pressure and make the most of your first dates!

But first, let’s dive into a hot topic: has dating culture become selfish? Plus, our Dear Damona question of the week tackles family versus gut instinct in rekindling old flames. 

DATING DISH (1:55)

Is dating culture becoming selfish?? Mashable thinks so!

A recent article says dating culture is becoming selfish, leaving many feeling insecure about finding love.

Frustration often targets dating apps, but the real issue may lie in the behavior of the people using them—rude, dismissive, and sometimes abusive actions are on the rise. This shift is affecting our ability to connect and leaving many of us worried about our dating prospects.

How do we tackle this issue? Damona shares that it starts with rethinking our approach and focuses on creating meaningful connections.

9:44 Mat Boggs

Mat Boggs is a YouTube dating coach and Brave Thinking Institute’s Love and Relationship division founder.

He has appeared on numerous national media outlets, including The Today Show, CNN Headline News, The Style Network, Oprah and Friends, ABC, and more. He’s also the best-selling author of Project Everlasting.

11:16 A Blurry First Date

First-date norms are evolving, leading to confusion about red flags. Damona asked, “How do I know if I need to run away from this person?” 

Mat agrees, suggesting that blurry first dates often stem from unrealistic expectations. He warns against expecting an instant spark or magical connection, which can lead to disappointment.

Instead, Mat recommends approaching first dates with an open mind and realistic expectations. By reframing our mindset, we can better assess compatibility without the pressure of finding “the one” immediately.

14:45 It’s Really Hard to Screw Up the Right Thing

“So often, people go into a first date with the primary goal of getting the other person to like them,” says Mat. 

This pressure to be perfect and seek approval can overshadow our own feelings. Instead, he emphasizes, “It’s really hard to screw up the right thing.” By being yourself and focusing on whether you enjoyed the date enough to want a second one, you shift the dynamic to a more genuine connection.

Mat shares the one simple question that needs to be answered on a first date. 

29:52 Keeping Secrets

What secrets do you not want to share on a first date? Mat emphasizes the importance of leaving a positive impression. 

Focus on stories that reflect personal growth and positivity, carefully avoiding oversharing unresolved issues. Mat says, “It’s about aligning what you share with the outcome you want, suggesting that sensitive topics should be saved for later, once trust is established.

He also suggests setting boundaries early on, recommending a gentle deferral for deeper topics: “If the topic comes up early, it’s okay to say, ‘That’s a great topic, and let’s save it for when we’ve been on a few more dates.'” 

Follow Mat on YouTube @MatBoggs and learn more about his MANifest Your Man Program.

DEAR DAMONA (43:38)

Submit your questions for our Dear Damona segment on Instagram, X, TikTok, or Facebook, and hear Damona’s answers live in a future episode!

IG voice memo from Tracy:

Hi, Damona. This is Tracy. I have a question for you. I’m trying to figure out the best way to decline a male friend’s 50th birthday party invite to Cabo San Lucas. I’ve known him since middle school, and we recently reconnected. He was my date for our 30th high school reunion last year. However, in the past few months, he’s been sending mixed signals.

He’ll be really consistent for a while and then nothing. We do live in two different states. However, when we started communicating, he said he was ready to retire and moved to my state to be closer to family. We’ve only seen each other twice over the past year, and although he’s mentioned coming to see me or me coming to visit him, he’s never followed through with those plans. And when I mention my intentions regarding dating and being in a committed relationship, it seems to really push him away. He shared that he just wasn’t ready, and just gave him some time to heal. He said he doesn’t feel like it’s fair for me to have a broken man. He’s been married twice and engaged three times. One wife passed away after they were apart for a few years, but she is the mother of his daughters, and one wife cheated on him. I know he’s been through a lot, and I respect him for his honesty and backed away. However, I still have feelings for him, and I feel like going on this trip will serve feelings that may not be reciprocated.

His daughter did send me the invite. However, we’ve only talked about the trip briefly, and my family has encouraged me to go. My sister and brother-in-law will be going as well. They’re really good friends with him, and they’ve been trying to hook us up for years. It is a family trip, and I know a few of his friends will be there, but I’m not sure if he’ll have a date there. Would it be a wise decision for me to decline? Thanks, Damona!

 

Learn more about bringing your best self when using dating apps. Listen to Damona’s episode with Dr. Alexandra Solomon: 365 Love Practices & AI Dating Concierge