You did everything right to prepare for the first date. You followed the steps. And he still didn’t show up.

You matched. You messaged. You asked for the phone call before agreeing to meet, which is more than most people do. 

The call went well. You felt that spark of possibility and let yourself get a little excited. You cleared your schedule, and then your phone buzzed at lunchtime. Work emergency. So sorry. Can we reschedule the first date?

That sinking feeling when someone cancels on you at the last minute is one of the most common kinds of disappointment in modern dating. 

You want to be understanding. You want to be flexible and open-minded. But at some point, giving someone the benefit of the doubt actually starts to cause real harm to your romantic future.

So what is the difference between giving someone a fair chance and giving someone too many chances? And when your gut is already telling you something, how do you know whether to listen to it or talk yourself out of it? 

A listener named Jenna wrote in:

“I matched with a guy on a dating app and followed your advice. After a week of messaging, I asked him for a brief phone call. He was so fun to talk to, and we seemed aligned. We agreed to meet for drinks after work. He lives two hours away, so we decided to meet in the middle. The day of the date came, and at lunchtime he texted and apologized that a work emergency came up and he had to cancel. He asked to reschedule and we found a day the following week. The day of that date comes, and he texts again with a similar work situation. Do I try again with this guy? When I think about setting up a third date, I’m not excited and I feel a little resistance. What’s a smart way to handle this?”

Here’s how to read the situation clearly, protect your time, and know exactly what to do next.

(00:03:30) You Already Did the Hard Part Right

Before getting into what to do next, let’s acknowledge what Jenna did: she asked for a phone call before agreeing to meet. That’s the pre-date screening step, and most people skip it entirely.

Here’s what a phone call actually tells you before you ever show up to a date:

• It gives you a real read on someone’s energy and how your conversation will flow in person
• It lets you ask the questions their profile left open, in real time, without the pressure of a first date
• It anchors you as a real person off the app, which actually reduces your chances of being ghosted
• It reveals the difference between someone who embellishes a little and someone who is making things up entirely

But here’s the part that often gets missed: the screening step is not just what happens on the call. It’s how they show up for the call, what they do after, and whether they follow through. 

The phone call is the beginning of the screen, not the end of it. And in Jenna’s case, this guy was already failing it before they ever got to a date.

(00:06:30) Benefit of the Doubt vs. Gullibility: There Is a Difference

Wanting to give someone the benefit of the doubt is not the problem. The problem is what happens when you have evidence and you choose to look past it anyway.

Giving someone the benefit of the doubt means not over-interpreting a single incident.

One canceled date could genuinely be a work emergency. Life happens.

Gullibility is what happens when you have a pattern and you explain it away.

Two cancellations before a first date, while he has given you nothing to be on the hook for yet, is a pattern.

There’s a concept in F the Fairy Tale called hopium: that addictive type of hope that keeps you investing in dating options that aren’t realistic. When you ignore what the evidence is showing you because of what you’re hoping it might mean instead, that’s not optimism. That’s a way of training yourself to accept flakiness as normal.

Jenna already knows. She said it herself: “When I think about setting up a third date, I’m not excited and I feel a little resistance.” 

That resistance is not fear of getting hurt. That is your gut telling you something your brain is still trying to negotiate with. And your gut is usually a few steps ahead for a reason.

(00:10:30) A Story About Giving Too Many Chances (Yes, It Gets Worse)

This exact scenario has happened before to Damona.  A guy with all the confidence and intention in the world approaches at a party, asks for a specific date, and makes it feel like finally, someone who shows up with clarity.

Friday morning arrives. He cancels for work.

Months pass. He resurfaces. The choice becomes: hold the line, or give it one more shot?

The answer, and what happened when the boundary finally got set out loud, is something every person who has ever held calendar space for a serial canceler needs to hear. The exact words are in the episode, and so is the plot twist at the end of the story that reframes the whole thing.

There is also a hidden cost to rescheduling that nobody talks about openly.

Every time you hold space for someone who doesn’t show up:

• You block off time that could go to someone who would actually be there
• You emotionally prepare for something that doesn’t happen, and that mental energy adds up
• You spend the days in between wondering if it will happen again, which is exhausting before you have even had one date
• You slowly normalize a standard of behavior that is not actually acceptable

If you can’t hold boundaries with your boss, what happens when the stakes are actually high? What happens when it’s not a first date on the line, but something that really matters?

(00:16:30) Why Everyone Is Canceling More Than Ever

This is not just one person and it is not just Jenna. Ghosting and last-minute cancellations are at a level that hasn’t been seen before in modern dating culture. 

Here’s what’s actually driving it:

1. The paradox of choice is not just about having options. It’s about having no criteria to sort them. Without clarity on what they’re actually looking for, people scroll endlessly and commit to nothing.
2. Dating fatigue is real. Overloaded calendars plus hours on apps plus constant notifications leaves very little room for genuine connection when a date finally rolls around.
3. People are treating dates like tentative plans. The fairytale myth that the right person will make everything effortless means people bail at the first sign of any inconvenience.
4. Nervous system overload is causing people to back away from things they genuinely want. Even if someone likes you, when they are already maxed out, adding one more thing pushes them over the edge, even if that thing is good.

None of this is a reflection of your worth. But all of it is worth understanding so you can stop interpreting other people’s chaos as information about yourself.

Sometimes it’s not about you at all. Sometimes the cancellation tells you everything about them and nothing about what you deserve.

(00:20:30) What to Actually Say When You’re Done

When you have decided this is not your person, you do not need a long explanation. You need one clear, direct message that closes the door with respect.

Send something like this:

“I really appreciate you wanting to reschedule, but it seems like timing isn’t working out for you right now and this isn’t a match. I wish you the best of luck.”

Keep it on the same platform you’ve been communicating on. Don’t overexplain. Don’t apologize for having a limit on how many times you’ll rearrange your life for a first date.

A few more things worth knowing before you get here:

• Set your own rules before you’re in the situation. If you know that two cancellations is your line, you won’t have to negotiate with your feelings under pressure when it happens.
• From the moment you match, keep the timeline to first meeting somewhere between one day and one week. Momentum matters and letting things drag out in the pre-date phase is where things start to lose priority.
• If you put a boundary in place and he responds by suddenly wanting to fight for it, let him show you. His response will tell you exactly what you need to know.

You can be open-hearted and optimistic and still have standards that need to be met. Those two things are not in conflict.

Your time is worth protecting. Every rescheduled date that doesn’t happen costs you more than just an evening.

Giving someone the benefit of the doubt means offering one fair chance and then paying attention to what they do with it. It does not mean holding the door open indefinitely for someone who keeps walking away from it.

The goal is not to be guarded. The goal is to be clear on what you need, trust what you’re already feeling, and move toward the people who are actually showing up.

💌 Got a question about someone who keeps canceling, figuring out when enough is enough, or anything else in the relationships that matter most to you? Send your question in a DM or voice memo on Instagram, TikTok, or Facebook, or send a voicemail or text to 424-246-6255. It might just be featured in an upcoming Dear Damona segment.

And remember: Dates & Mates covers all the relationships that matter in your life: the people you’re dating, your closest friends, your family, your coworkers, and most importantly, yourself.

📝 Ready to see what patterns are actually showing up in your dating life?Download the free Date Tracker at damonahoffman.com/datetracker. It helps you see patterns and move forward with clarity

Valentine’s Day is supposed to be the Super Bowl of Love. 

Big gestures, big expectations, big pressure. But somewhere along the way, we got sold a fairytale version of relationships where the right person makes everything effortless, passion never fades, and if it’s meant to be, you’ll just know.

Real relationships, the kind that survive and thrive, aren’t built on magic. 

They’re built on pillars: shared goals, shared values, clear communication, trust, and mutual respect. These aren’t the sexy parts of love we see on Instagram, but they’re the reason relationships last.

For this Valentine’s Day episode, we looked at relationships that have stood the test of time and asked five leaders in love two simple and powerful questions:

• What is the biggest relationship myth you once believed that you’ve changed your mind about?
• What is the pillar that actually keeps your relationship still standing today?

Some of their answers might surprise you. Some might challenge what you’ve been taught. And some might give you permission to release a version of love that was never actually serving you in the first place.

Because this Valentine’s Day, you don’t need to chase a fairytale. You need to rewrite the myths and live your own love story.

(04:00) John Kim: Love Isn’t Easy Just Because You Did The Work

John Kim, aka The Angry Therapist, has been with his partner for 8 years. He’s a therapist, podcast host, and bestselling author of books like Single on Purpose and I Used to Be a Miserable F*ck.

He shared:

“The greatest myth about love that I have proven to be untrue is that if you work through wounds and attachment styles and learn to fight without fighting and go to therapy and all that, then love will be easy.”

Here’s what nobody tells you: working on yourself isn’t a one-time thing. It’s not a constant. It’s an everyday thing.

John and his partner are in their 40s and 50s. Things like perimenopause and ADHD and raising children showed up in ways they never anticipated because they’d never been this age before.

Love is a constant growing, evolving greenhouse, and even when it’s healthy, there are hard days. The work of choosing each other and growing from that container is a lifelong process.

His Pillar: The Importance of Repair

“If you can’t both learn how to repair, the plane will eventually go down. Repair is at the top.”

When you show up ready to do the work with your partner and to learn with them, there are always moments for repair. And those moments of repair don’t just repair the relationship with your partner. Sometimes they repair something deeper in yourself.

(08:00) Carol Allen: Love Can Sneak Up on You Like Moss

Carol Allen is a Vedic astrologer and relationship coach of 35 years. She’s been with her husband for 33 years, and she’s one of the leaders in examining how we build a successful love life.

She shared:

“What I now know to be true that I didn’t used to think was true is that you can fall in love slowly. Love can sneak up on you. I joke now that there’s two ways to fall in love: you can be struck by lightning, which of course can lead to scorched earth, or you can be struck by moss and then wake up one day and everything is green.”

That was how Carol and her husband fell in love.

They both felt a connection, and then gradually grew to realize this beautiful thing was happening that has lasted all these years.

This is a major theme in F the Fairytale: true connection develops over time.

It’s not instant chemistry. It’s slow love, building connection and rapport, seeing how somebody shows up for you, building it block by block, and then the attraction actually deepens.

Her Pillar: Always Be On Each Other’s Side

“The biggest pillar of long-term love is to always be on each other’s side. Always make the other person feel emotionally seen and validated and cared about. If you always feel like they are on your side, that even when there’s a conflict, you’re gonna get through it because it’s you and the other person working on the conflict as opposed to going at each other.”

Studies all over the world confirm this: both people need to be happy.

You can’t be happy with an unhappy person. So if you find someone you can love, who loves you, who’s happy and likes their life and likes the people in their life and likes themselves? 90% of your job is done for you.

(12:00) Orna & Matthew Walters: Shared Values Are The Glue

Orna and Matthew Walters are the co-founders of LoveOnPurpose.com and authors of Getting It Right This Time. They’ve been together for 19 years, married 17, and they both found love later in life in their 40s.

Orna shared her myth:

“A myth I used to believe about love is that all the good ones were taken. I used to be really attached to that story.”

Matthew shared his:

“One of the biggest myths I believed about love was that if you hung around a friend long enough that eventually they might change their mind to become a romantic partner.”

All the good ones are taken.

Sound familiar? It’s a limiting belief that shows up in every decade.

When we get overly focused on the options that aren’t available to us, we miss what’s right in front of us. You have the power to rewrite your own love story, starting today.

Getting friend-zoned and waiting for the tide to turn?

While there are stories of friends who fell in love years later, a lot of times you find that you don’t have the attraction piece. And if you’re perpetually friend-zoned, that could be a sign you’re choosing unavailable people or reading signals incorrectly.

Their Pillar: Shared Values

“We can’t think of anything that separates from that. Shared values is it. It’s the most important thing. You’re going to have disagreements, you might have conflict or misunderstandings. And when you have shared values, it makes it very easy to get back on the same page again.”

When you look at the world in the same way and believe the same things about who we are as humans and how we live our lives, that’s worth so much more than shared interests or physical attraction. That’s the kind of thing that aligns a couple: you and your partner against the world.

(19:00) Lily Womble: You’re Never Too Much for the Right Person

Lily Womble is the author of Thank You More Please, founder of Date Brazen, and a feminist dating coach. She’s been with Chris for 8 years, married for almost 3.

She shared:

“My biggest dating myth that I used to believe is that I was too much to find the right partner. I was socialized to believe that as a woman, I needed to make my needs smaller, make my wants smaller, that I was being too picky, that I was being too judgmental if I set boundaries with the wrong people for me.”

This socialization led her to settle hardcore and judge herself for wanting what she wanted.

She ended up in terrible romantic relationships with people who could not meet her needs.

Now she knows: it’s really human and normal to want what you want and you are never too much for the right person. You can never say the wrong thing to the right person for you.

Her Pillar: Game to Play and Co-Create

“A pillar of long-term love that is crucial is someone who is game to play and game to co-create. This language comes from improv: you’re game to co-create, you’re game to listen and react and play together. That sense of playfulness and co-creation has served me so well.”

Co-creation means:

• Planning the first date together
• Defining the relationship together
• Getting out of your own way sometimes
• Being creative with your partner and being open to listen
• Being open to receive the kind of love and support you desire

We start out as kids playing all the time, then we learn to adult and lose that sense of play. Bring it back. Even if you’re not partnered yet, bring back that sense of play in your life today and you will find others who want to play with you.

(25:00) Seth Hoffman: Real Love Soothes the Heart and Soul

Seth Hoffman is a TV writer/producer and Damona’s husband of 18.5 years.

He shared:

“The one myth about love that I used to believe is that when people were in love, their feelings were just at a 10 all the time. It was just all these big feelings all the time and it was hard to even think straight because you are in love. That kind of love feels like your heart going really fast. The kind of love that I experience and the kind of love that I really cherish is a kind of love that slows my heartbeat down and makes me feel calm and safe.”

We’re so addicted to rom-coms and fairytales. They tell us it should be dramatic, high and low, intensity all the time.

But when you’re looking for the trust and the answer out of the gate, you’re going to come up with tons of questions.

When you’re committed to slow love and building it over time, then the trust will unfold naturally. Then it becomes obvious: this is the person you want to build your life with and pour into and have invested in you.

His Pillar: Trust Above Communication

“The one pillar that I think is most important is trust. My stock answer used to be communication, and I think communication is really important. But for me, above and beyond communication is trust. If you fully trust the person you’re with and you know that the person you’re with fully trusts you, then you know that if they’ve done something that pisses you off, that the intent isn’t to piss you off.”

Before you even start communicating to understand what happened, you go into that conversation knowing the thing that upset you wasn’t intentional. It’s just a conversation about what happened as opposed to believing there might be ulterior motives.

Trust is the final pillar in F the Fairytale, and it’s the pillar that takes the longest time to build. 

Stop Chasing the Fairytale

If there’s one thing to take away from these conversations, it’s this: long-term love doesn’t fail because people don’t want it badly enough. It struggles because we’ve been handed myths that were never designed to support real human relationships.

We were taught that love should be effortless, that the right person will heal your wounds, that conflict is a sign you chose wrong, and if it’s meant to last, you won’t have to work so hard at it.

But every one of these relationships survived not because the fairytale came true, but because someone was willing to question it. To replace a myth with a pillar. To stop waiting for love to save them and start building love that could actually hold them.

That’s the heart of F the Fairytale. It’s not about becoming cynical. It’s about becoming empowered. It’s about rewriting the stories that keep us stuck in dating and relationships and creating a love story that actually fits your life.

💌 If today’s episode resonated, pick up F the Fairytale and start questioning the myths you inherited. Start building the kind of love that can actually last.

Find it on Amazon, Barnes and Noble, or from your local bookseller. Links at fthefairytalebook.com. 

💌 Got a question about revenge reporting, trusting your gut when you can’t explain why, handling retaliation for setting boundaries, or navigating dating apps safely?

Whether it’s about ghosting that feels safer than communicating, dealing with people who won’t take no for an answer, getting banned unfairly, or any other challenge in the relationships that matter to you, we’re here for all of it.

Send your question in a DM or voice memo on Instagram, TikTok, or Facebook, or send a voicemail or text to 424-246-6255. It might just be featured in an upcoming Dear Damona segment.

And remember: Dates & Mates covers all the relationships that matter in your life: romantic partnerships, friendships, family dynamics, work relationships, and most importantly, the relationship you have with yourself.

📝 Ready to track what’s working (and what’s not) in your dating life? Download the free Date Tracker at damonahoffman.com/datetracker. It helps you see patterns and move forward with clarity

If you are wondering if everyone else around you just magically knows how to date, you’re not alone.

It can feel like there’s some secret handbook you missed while everyone else got theirs in high school?

We’ve been told our whole lives that dating should just come naturally. That attraction, communication, and building trust are things we’re born knowing how to do. That by your late twenties, you should have all this figured out already.

But here’s the actual truth: dating is a skill. It’s a set of learned abilities. How to communicate, how to attract, how to build trust and connection. And like any skill, whether it’s learning to drive or learning to speak a new language, you get better with practice.

It’s about recognizing that being new to dating doesn’t make you naive. It makes you a beginner. And every expert was a beginner once.

This week, a listener who asked to be identified as Butterfly wrote in with a situation that so many late bloomers are navigating.

She shared:

“I am now in my late twenties and struggling to find a mate. I had strict parents and wasn’t allowed to date in high school. In my early twenties, I never tried with relationships, and now that I’m getting older, I’m in a place where I’d like a relationship, but I can never find the first person. I feel like the men I’ve tried to date have taken advantage of my naivety and wasted my time with no real intentions. I don’t know how to build a genuine bond with someone and don’t know what to look for and what to avoid. Can you help?”

This is a question that goes deeper than just getting dating advice: it’s about stepping into a space where you feel behind, learning to trust yourself when you’re building new skills, and protecting yourself without closing off to opportunity.

(04:00) You’re Not Naive, You’re a Beginner (And That’s Actually Better)

Here’s the reality: a lot of people who dated in high school or college went through the exact same trial and error you’re experiencing now. They just went through it earlier.

They made the same mistakes. They asked the same questions. They felt just as confused.

Being new to dating doesn’t make you naive. It makes you a beginner. And there’s a crucial difference:

• Naive means you don’t know what you don’t know
• Beginner means you’re actively learning, building competence, getting your reps in

The story you tell yourself matters. If you tell yourself, “I’m behind, I’m naive, people are taking advantage of me,” that fear will lead every interaction.

But if you reframe it as, “I’m building a skill I didn’t get to practice earlier,” you give yourself permission to learn without shame.

(08:00) They’re Not Manipulating You, They’re Self-Focused

When Butterfly says she feels like men have taken advantage of her naivety, there’s something real underneath that fear. But it might not be quite what she thinks.

Most daters aren’t sitting around plotting how to manipulate beginners. They’re too consumed with themselves and what they want to worry about trying to manipulate anyone.

The reality is more transactional than malicious. People are laser-focused on their own experience, their own needs, what they’re trying to get met.

That’s not manipulation. That’s self-motivation. That doesn’t make it a good thing but it reduces the emotional charge.

What feels like manipulation is often just inexperience preventing you from reading signals and intentions early on. When you don’t know what to look for yet, you miss the cues that someone more experienced would catch quickly.

The good news?

You can learn to see those signals. And the more practice you get, the clearer they become.

(11:00) Green Flags: Consistency Between Words and Actions

So what should you actually look for? What separates someone worth your time from someone who’s going to waste it?

Your north star: consistency between someone’s words and actions.

A lot of times when people say they’re being manipulated or someone’s wasting their time, when you play back the tape, there were signs early on.

Cues in their profile. Things they said in the first few conversations.

Pay attention to:

• What someone says in their profile about what they’re looking for
• How they talk about prior relationships (negative? dismissive? still processing?)
• How they relate to other people in their life (work, family, friends)
• Whether their actions match what they say they want

The biggest predictor of what someone will do in the future is what they’ve already done. People don’t change a whole lot.

Sometimes we ignore these signals because we want the narrative to fit. We’re so focused on finding a relationship that we filter out anything that doesn’t align with what we want to be true.

We blow through the stop signs. We ignore the red flags. We filter out what doesn’t work for us because we’re trying so hard to make it work.

You can start to notice patterns and outcomes by using a Date Tracker, which is a vital (and free) resource for all daters.. Just starting to record what’s actually happening on dates and how you’re feeling will start to chart a path in the direction you want to go.

(16:00) Name and Narrate: A New Dating Strategy for 2026

Here’s a brand new dating strategy: name and narrate.

Start naming the thing you’re feeling out loud. Call out your fear. See how they react to it.

Here’s what this looks like in practice:

You’re on a date and someone puts their hand on the small of your back, but you’re not comfortable with that yet. Instead of squirming and hoping they get the hint, just say it: “We’re not at that point yet.”

At a singles event feeling awkward? Walk up to someone and say, “Aren’t these events always awkward? I never know what to say to break the ice.”

By naming the thing you’re feeling, you:

• Affirm your own power and agency
• Create an opening for connection
• Give the other person permission to be honest too

There’s a chance the other person is feeling the exact same way, and now you’ve given them permission to be real with you.

Stop setting aside your discomfort for someone else’s comfort.

Name the thing. See what how they respond.

(19:00) Building Connection Starts Where You Already Are

Butterfly says she doesn’t know how to build a genuine bond. And here’s what’s important to remember: building a genuine bond isn’t something that happens overnight.

It’s built slowly through shared experiences, through honest conversations, through showing up as your real self, not who you think somebody wants you to be.

So don’t put the cart before the horse. Don’t come in craving a bond so intensely that you push through things too fast and blow through red flags.

Start where you are already comfortable:

1. Ask yourself: what do I actually enjoy doing?
2. Invite someone into those spaces with you
3. Build from there

Connection happens when:

• Both people are willing to open up
• Both people are willing to be a little vulnerable
• Both people are willing to share thoughts and feelings that matter

If someone isn’t meeting you halfway in building that connection, that’s valuable information.

But if you come in hot, fixated on the finish line, you’ll miss the initial steps that actually build trust: feeling seen, feeling heard, noticing whether their words match their actions.

Every Date is a Learning Opportunity

You’re not looking for perfection. You’re looking for someone who shows up with genuine intentions and treats you with respect.

Go into this experience of dating thinking of it as practice.

You need to get into as many conversations as you can to get your reps in. Every date, every conversation, every experience is teaching you something about what feels right and what doesn’t.

If you think of it as, “Hey, we’re just practicing here,” it takes the pressure off. We’re not going all the way to soulmate, we’re not going all the way to bonded. We’re just like, “Are we having a good time? Are we traveling the same path in life? Do I feel good when I’m with you?”

That is enough for the first step.

💌 Got a question about starting over, building confidence, or figuring out what you actually want in dating?

Whether it’s about late blooming, learning to trust your gut, protecting yourself without closing off, or navigating dating as a complete beginner, we’re here for all of it.

Send your question in a DM or voice memo on Instagram, TikTok, or Facebook, or send a voicemail or text to 424-246-6255. It might just be featured in an upcoming Dear Damona segment.

And remember: Dates & Mates covers all the relationships that matter in your life: the ones you’re building, the ones you’re healing, and most importantly, the relationship you have with yourself.

📝 Want to keep track of what’s working (and what’s not) in your love life? Download the free Date Tracker at damonahoffman.com/datetracker

The Cosmic Chapter Is Turning & What It Means for Your Love Life: Why 2026 Astrology Says Dating Is About to Shift

Before we can even talk about swiping, texting, or defining the relationship this year, there’s a bigger question we need to ask: What is the astrological roadmap for 2026?

Something’s happening in dating lately. Something under the surface that’s getting in the way of communication, connection, and every important relationship. The apps feel broken. Ghosting is everywhere. Commitment seems impossible.

But what if the issue isn’t your profile or your approach? What if it’s bigger than that?

Sometimes we need to zoom out. We need to widen the lens beyond just our little town, beyond the confines of our country, our continent. Look into the universe and see what clues and signs are there for us from the perspective of ancient wisdom, of the cosmos.

This week, we asked Danny Santos, shaman, healer, astrologer, and tarot reader, to look at the major cosmic themes shaping love, communication, and connection in the months ahead. 

Here’s what’s coming for love in 2026.

(03:00) Meet the Shaman Who Saw This Coming

Danny Santos is a world-renowned astrologer featured in the New York Post, Vice, Bustle, Well+Good, and Buzzfeed.

He’s more than an astrologer. Danny is a shaman, reiki master, tarot reader, medium, psychic, and life coach who traveled to Peru to receive the blessing of the Shabo tribe to work with plant medicine.

His prediction for 2026? The cosmic chapter is turning. Eight years of stagnant energy is about to lift. When it does, everything shifts.

(05:00) Why Dating Activity Dropped 7% (And What Astrology Predicted)

The numbers don’t lie: dating activity on apps dropped 7% in 2025. People got exhausted. The flakiness, ghosting, and mismatched intentions became too much.

Astrology saw this coming.

For eight years, Uranus (the planet of innovation and forward motion) moved through Taurus, a comfort-seeking sign that resists change. Taurus wants to stay home, avoid risk, stick with what’s familiar. Innovation in a resistant sign creates a slowdown. Dating activity stalls. People retreat.

2026 changes the game.

Uranus moves into Gemini, the sign of communication, dating, and community. Gemini craves social connection, new experiences, and conversation. The cosmic brake on dating releases.

What this means:

• In-person connection will explode
• Community events and group dating return
• Technology finally innovates (think augmented reality, new connection methods beyond swiping)
• People will want to go out again

If you’ve been waiting for a shift, it’s here.

(10:00) February 20th: A Once-in-36-Years Paradigm Shift

February 20th, 2026: Saturn and Neptune meet in the sky.

This happens once every 36 years. Last time? 1989. No internet. No dating apps. No texting. That era is over. This one begins.

Saturn represents commitment and structure. Neptune represents romance and spiritual connection. Their meeting creates a fundamental shift in how we approach relationships.

What changes:

• Commitment becomes valued again. Not casual dating. Not situationships. Real partnership. The conversation shifts from “keep your options open” to “find someone worth choosing.”
• Self-love stops being optional. This transit pushes people to do inner work before partnering. That foundation creates healthier relationships.
• Romance transforms. Fairy tale gestures lose appeal. Emotional safety, consistency, and genuine presence become what matters.

Dating has felt shallow and transactional lately. This transit signals the turning point. February 20th marks the beginning.

(14:00) Summer 2026: The Season When Everyone Wants Commitment

June 30th, 2026: Jupiter enters Leo. Everything transforms.

Jupiter brings expansion and opportunity. Leo brings loyalty and partnership. Together, they create desire for commitment. Not casual dating. Not undefined situations. Actual partnership.

Summer 2026 brings massive dating activity, but this isn’t casual hookup season. People want loyalty. They’re ready to attach. They want to find their person.

Then August brings the eclipses.

Eclipses create rapid, profound change. The August eclipses highlight individuality versus partnership, freedom versus commitment.

The moment arrives when people get serious:

• Casually dating singles suddenly want definition
• Uncertain couples make decisions
• Commitment stops feeling terrifying

The cosmic timing for finding love? Summer 2026.

(26:00) Year of the Horse: Why Your Manifestations Accelerate

2026 is the Year of the Horse in Chinese astrology. Horses represent forward motion, adventure, excitement, joy.

For your love life: whatever you focus on appears faster than usual.

This energy rewards risk-takers, not people playing safe. How to work with it:

Prioritize playfulness. Strong relationships this year build on fun, adventure, shared joy. Taking dating too seriously backfires. Lighten up. Try ridiculous dates. Playfulness attracts.

Take risks. Put yourself out there. Message first. Suggest the date. State what you want honestly.

Clarify your desires. Faster manifestations require clear intentions. Vague focus attracts vague results. Clear focus brings fast delivery.

Playing small in your dating life? The Year of the Horse gives permission to go bigger.

The universe is shifting. Use this energy or let it pass.

Summer brings partnership-focused energy. Commitment returns to favor. Manifestations accelerate. Astrology believer or not, these patterns are real. Waiting for the right time to get serious about love? This is it.

Want to book a session with Danny Santos? Visit santoscrystalvisions.com and use code DATES for 10% off your first session. Follow him on Instagram @SantosCrystalVisions for daily cosmic guidance.

If you’re newly single after being hurt, the dating landscape probably feels impossible. You’ve learned that vulnerability can be weaponized. That people disappear. That trust gets broken. So somewhere along the way, you developed two extreme responses. 

Either you’re telling someone your entire life story on date one, hoping that if they know the worst of you they’ll stay. Or you’re so locked down that three dates in, they still don’t know anything real about you.

We’ve been told that vulnerability is brave, that showing up as your real self is the key to connection. But what nobody explains is what that actually looks like in practice, especially when you’re trying not to scare someone off on a first date.

The truth is messier and way more hopeful than either extreme. Healthy vulnerability isn’t about choosing between oversharing or shutting down. It’s about understanding why you swing between those two poles, recognizing what both are actually protecting, and learning to share in a way that builds real trust instead of just testing whether someone will accept

A listener named Brian reached out with a struggle that’s way more common than he realized.

He shared:

“I have two dating modes. Either I dump all my emotional baggage on the first date, or I stay super chill and keep everything surface level, even when I actually want to go deeper. I’ve been hurt enough times that I just don’t trust people to really be there for me anymore. How do I open up without scaring someone off or feeling like I’m being way too vulnerable too soon?”

This goes deeper than dating nerves: how do you find a way to actually let someone in when both extremes feel safer than the middle?

(03:20) The Same Fear, Two Different Defense Strategies

Here’s what doesn’t get talked about: oversharing and shutting down aren’t opposites. They’re the same strategy wearing different masks.

When you dump everything on date one, you’re running a test. Your logic is: if I tell you the worst parts of me and you stick around, you’ve proven you can handle me. When you stay surface-level, you’re running the opposite test: if I don’t let you in, you can’t hurt me.

But here’s what they have in common:

• Both are about control, not connection
• Both prevent something instead of building something
• Both keep you locked in a pattern that guarantees the outcome you’re afraid of

One tries to control whether they’ll accept you. The other tries to control whether you get hurt. Neither leaves room for actual vulnerability because both are defense mechanisms disguised as honesty.

(06:00) Your Distrust Isn’t Broken, It’s Smart

Let’s name what’s real: you’ve been ghosted. You’ve been strung along. You’ve had your heart handled carelessly by people who said they cared.

Your nervous system didn’t overreact to that. It learned. It decided to keep you safe by keeping you guarded. That’s not a character flaw. That’s your body doing exactly what it’s supposed to do.

The mistake isn’t that you learned not to trust. The mistake is thinking you have to completely unlearn it to find someone real. You don’t.

What you actually need to learn is this: I can survive disappointment.

Think about any skill you’ve ever gotten genuinely good at. Basketball. Writing. Cooking. You don’t become good by only attempting things you’ll definitely succeed at. You miss. You adjust. You try again. Each miss teaches you something about your technique. The more you practice, the less each individual miss destroys you because you know you can keep throwing.

Dating works identically. The goal isn’t to never get hurt. The goal is to become someone who can get hurt and come back stronger, with wisdom instead of scars.

(11:20) Vulnerability Isn’t a One-Way Dump

This is where most people get it completely wrong. They think vulnerability means baring your soul, and the bigger the revelation, the more vulnerable you’re being.

That’s not vulnerability. That’s confession.

Real vulnerability is a conversation, not a presentation. It’s gradual. It’s reciprocal. It’s small moments that build trust instead of one giant leap that either lands or crashes.

Here’s how it actually works:

1. Share something authentic but not catastrophic. Maybe a two or three on the intensity scale. An embarrassing work moment. A small fear. Something real but not your deepest wound.
2. Watch what comes back. Do they respond with curiosity or judgment? Do they ask follow-up questions? Do they share something that feels like meeting you halfway?
3. Find connection points. When someone shares about their work travel and how it made relationships hard, you don’t respond with your own trauma story. You say, “I love to travel too, and I understand how that creates distance.” You’ve just told them something real about yourself and found common ground. That’s where vulnerability actually lives, in the small moments that show you understand them.

This is the difference between compatibility and concession. One is reciprocal. One slowly breeds resentment.

(19:00) Rewrite the Narrative Running Your Love Life

There’s probably a story you’ve been repeating to yourself for a long time:

“I always mess this up.” “I’m going to end up alone.” “People can’t be trusted.”

These aren’t just thoughts. They’re instructions you’re giving your brain about what to look for. And your brain is incredibly obedient. It finds evidence to prove you right.

If you keep telling yourself you’re getting it wrong, you won’t recognize it when you’re actually getting it right. You’ll second-guess every good moment. You’ll interpret kindness as manipulation because you’ve already decided that’s what to expect.

The work is simple but not easy: name the story, then replace it.

Instead of: “I keep messing this up” Try: “I’m learning to be vulnerable in a world that doesn’t always feel safe, and I’m getting better at it”

Instead of: “I’ll end up alone” Try: “I’m someone who attracts the right people when I’m being myself”

This isn’t toxic positivity. It’s redirecting your attention toward evidence that already exists in your life, the moments when you showed up authentically and someone met you there with curiosity. Those moments happened. Your brain just learned to ignore them because they didn’t fit the story you were telling.

You don’t have to choose between all-in and locked-up.

Healthy vulnerability isn’t about finding the perfect script or waiting until you’re 100% sure. It’s about learning to share gradually, watching for reciprocity, and trusting yourself to handle whatever happens next.

Your job on a first date isn’t to get it perfect. Your job is to practice being human, messy, and real, and to notice who responds to that with curiosity instead of judgment. That’s how you find someone worth your vulnerability.

💌 Struggling with oversharing on first dates, emotional walls that won’t come down, or finding the balance between protecting yourself and actually letting someone in?

Whether it’s about rebuilding trust after being hurt, learning to read the room early on, figuring out when it’s safe to go deeper, or rewriting the narratives that keep you stuck, we’re here for all of it.

Send your question in a DM @DamonaHoffman on Instagram, TikTok, or Facebook, or leave a voicemail or text at 424-246-6255. Your question might be featured in an upcoming Dear Damona segment.

And remember: Dates & Mates covers all the relationships that matter in your life—romantic partnerships where you’re learning vulnerability, friendships where you’re opening up, family dynamics that require courage, work connections that need authenticity, and most importantly, the relationship you have with yourself.

📝 Ready to see your dating patterns and understand where you’re oversharing or holding back?

Download the free Date Tracker at damonahoffman.com/datetracker. It’s designed to help you recognize your tendencies and move forward with clarity.

Have you ever felt like you’re drowning in matches but starving for actual dates?

You know that feeling when you’re scrolling through your matches and seeing the same faces year after year, app after app. When you’ve got eight plus conversations going but they all seem to fizzle the moment you try to make something real happen.

We’ve been told that more options is always better. That the problem with dating apps is you’re not swiping on enough people or you’re being too picky.

But here’s what happens in real life: having 50 matches doesn’t solve the problem. It just creates a new one. The issue isn’t the number of options. It’s how you move through them.

It’s about what we’re really looking for when we open these apps, what gets in the way of actually finding it, and whether the algorithm is working with you or against you.

This week, a listener wrote in with a situation that so many of you are navigating right now.

She shared:

“I end up with 50 plus matches like within 48 hours. Some of them I suspect are like dead profiles or just the algorithm or robots—literally it’s the same people for years and years. I end up with eight plus conversations and either get too overwhelmed or end up with just a few dead conversations. And then there’s the other situation of having a fantastic phone call, scheduling a date, having him reschedule and ask for a rain date but not give a suggestion. And then there’s another guy I went on a couple dates with five years ago. I see him in a bar, message him on Instagram. He says, definitely, you look great. And then he drops off the conversation when I say, okay, great, let me know when you wanna get together. What is going on?”

This is a question that goes deeper than bad luck with matches: why do options feel like a trap instead of a gift?

(05:00) Maximizers vs. Satisfiers: Why Your Brain Breaks

There are people called maximizers who research everything and want to see all options before deciding.

Then there are satisficers who find an option that works and stop looking.

Here’s the thing: dating apps are built for satisficers. If you’re a maximizer seeing 50 matches, the app doesn’t care that you need more information. It just keeps feeding you more people.

The result? You burn out.

(07:40) No Framework = No Progress

Without a screening system, you start conversations with anyone who looks decent. You’re in eight DMs going nowhere. The potential ones fizzle. The interested ones ghost.

Your screening process needs to be built around your goals and values, not around who’s cute or who has the best text banter.

Ask yourself:

• What are my non-negotiables?
• Do their words and actions match?
• How quickly do they move from chatting to actually making a plan?

When you can answer these, you move through matches with purpose. You tighten your filters. You don’t engage with people who don’t align with what you’re looking for.

(13:00) The Dirty Little Secret About the Algorithm

Dating apps flood you with matches in the first two weeks. When you sign up (or return after time away), the algorithm pushes your profile to everyone. Some profiles are real. Some are dead accounts. Some aren’t people at all.

But the app doesn’t care. It just wants the dopamine hit so you stay and pay.

Two or three weeks in, the options dry up because many weren’t real options to begin with.

What you’re doing by signing on, getting overwhelmed, signing off, and switching to another app is burning your energy. The algorithm never gets a chance to learn who you are. So you end up seeing the same faces year after year because you’re hitting reset every time you take a break.

Give the algorithm time to actually work for you.

(17:00) Interest vs. Intention

Someone can be interested without any intention to follow through. They like the validation. But when it comes time to actually make a plan? They disappear.

Watch what they do, not what they say.

Interest: “You’re amazing, we should definitely hang out.”

Intention: “I’m free Wednesday or Saturday. What works for you?”

One is a feeling. The other is a plan.

When someone disappears the second you ask for specifics, that’s a clear signal. Thank and release them. You are not asking for too much.

(19:00) Coins in a Fountain, Not Fish on a Line

You see someone who looks great and start building a future in your head. You’re already planning your wedding together before you’ve heard their voice.

This is future-casting. And it’s how you lose yourself.

Think of your matches like coins in a fountain. You throw one in and make a wish. Some come true. Some don’t. But you don’t put your whole heart into that coin before you’ve even thrown it.

You’re looking for momentum. You’re looking for consistency. You’re looking for someone whose actions match their words. If you don’t see all three early on—within that first week or two of dating—you’re not going to magically find them later.

Stop waiting for people to show up differently than they already have.

You are not asking for too much when you want someone to actually make a plan. You’re not being too picky when you walk away from people who say “definitely” and then disappear. You’re protecting your time, your energy, and your hope. And that is what matters most.

💌 Got a dating app horror story or match dilemma?

Whether it’s about feeling overwhelmed by options, dealing with flaky behavior, or learning how to protect your energy from the people who drain it, we’re here for all of it.

DM @DamonaHoffman on Instagram, TikTok, or Facebook, or leave a voicemail or text at 424-246-6255. Your question might be featured in an upcoming Dear Damona segment.

And remember: Dates & Mates covers all the relationships that matter in your life—your dating situations, your friendships, your family dynamics, your work relationships, and the relationship you have with yourself.

📝 Want to keep track of what’s working in your dating life? Download the free Date Tracker at damonahoffman.com/datetracker