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