Have you ever been stuck managing someone else’s emotional chaos when you’re just trying to get your work done?

This week we’re tackling a different kind of relationship, one that sometimes gets overlooked: the one between you and your boss. 

We talk a lot about emotional safety and clear communication, especially in romantic relationships. But what happens when someone in a professional setting starts treating you like their therapist or their best friend? And you can’t just hit mute, unsubscribe, block and delete and walk away.

Listener Linda is dealing with exactly this:

“My boss is nice, but she talks to me like I’m her best friend—like way too much info. Relationship issues, family drama, sometimes mid-meeting she’ll start telling a story that’s got nothing to do with work. It’s super uncomfortable, but I also don’t wanna create tension or seem like I’m judging her. How do I keep things professional when the person in charge doesn’t seem to know where the line is?”

If you’ve ever felt caught between empathy and awkwardness at work, you’re not alone. And no, you’re not being cold for wanting boundaries. You’re being honest.

(3:00) When “Nice” Doesn’t Mean “Safe”

Here’s something most people miss: just because someone feels safe around you doesn’t mean they’re creating a safe space for you.

Linda’s boss probably thinks she’s building trust. But what’s really happening? Emotional dumping. She’s offloading her personal problems onto someone who doesn’t have the power to say no or redirect without risking her job. That creates an imbalance of power.

When your boss overshares, you end up managing their discomfort instead of acknowledging your own. You’re trying to make them feel okay while you feel increasingly uncomfortable yourself.

(5:00) The Post-Pandemic Boundary Blur

Remember about five years ago when something completely changed the way we work? Yeah, the pandemic.

When everyone shifted to working from home, the lines between personal and professional actually got clearer. You had to make deliberate choices about whether to use meeting time for personal conversation or stay focused on tasks.

But now that people are back in the office? All bets are off. The lines are blurred again.

When those expectations don’t match, one person thinks they’re bonding while the other is just trying to get through their to-do list.

(8:00) You’re Not Being Selfish, You’re Being Clear

Look at what Linda said: “It’s super uncomfortable, but I also don’t wanna create tension.”

Do you hear what’s happening? She’s prioritizing her boss’s comfort over her own.

This pattern shows up everywhere. In romantic relationships, at work, and with family. We don’t say what we’re really feeling because we’re worried about the repercussions.

But here’s the truth: boundaries don’t make you cold. They make you trustworthy because people know where they stand with you.

(10:00) Three Ways to Redirect Without Drama

What do you actually do when your boss starts oversharing? You have options that don’t require confrontation.

• Subtle Redirection in the Moment: Acknowledge what she said, then redirect: “Wow, that sounds like a lot. So should we circle back to the budget review?”
• Set Timing Boundaries: Create a container: “Hey, I want to give this project my full attention. Can we pick this up after five?” You’re not saying no. You’re just saying not right now.
• Clear But Compassionate Reframe: For persistent oversharing: “I really value working with you, but when we bring personal challenges into the workplace, I’m not able to stay focused and do the best job for you. Maybe we can reframe our conversations to stay focused on the work.”

(16:00) Why This Matters Beyond Your Job

How you handle boundaries at work shows up everywhere else in your life.

If you’re stuffing down your feelings to keep the peace with your boss, you’re probably doing it in your romantic relationships too. 

Practice boundary setting here so you can practice it everywhere.

You’re allowed to protect your peace. Even if it’s awkward. Even if the person crossing the line is technically above you.

Professionalism and compassion are not mutually exclusive.

Workplace boundaries aren’t about being difficult.

They’re about protecting your capacity to do good work while maintaining your emotional well-being. Honoring your boundaries is the most compassionate thing you can do for everyone involved.

💌 Ask us anything…don’t be shy!

Whether it’s about dating, relationships, navigating a tricky boss, or what the heck to say when someone crosses a line, 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 isn’t just about romantic relationships anymore. It’s about the people who matter most: partners, friends, family, coworkers, and you.

📝 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

Your best friend knows everything about you except the one thing that could change everything between you.

Your best friend is the safest relationship in your life. People already think you’re dating. You can finally picture a future with someone, except there’s one problem: she’s straight, and you’re terrified that telling her how you feel will destroy everything.

This week, a listener wrote in about being in love with her best friend:

“I’m a queer woman in my thirties and my best friend is straight. We’ve gotten so close that people think we’re dating. My therapist says she’s the safest relationship I have. I think she’s my person. I’ve never been able to visualize a long-term relationship before this. But it’s getting harder to listen to her talk about dates with men. Do I tell her how I’m feeling and risk our friendship? Or do I stay quiet and protect my heart while keeping this incredible friendship I never want to lose?”

If you’ve ever questioned whether safety means compatibility, or wondered if speaking your truth is worth the risk, here’s what you need to know.

(3:00) When “Safe” Doesn’t Mean “The One”

Emotional safety is foundational for any relationship, but it doesn’t automatically mean you’re meant to date someone. This is one of the biggest areas of confusion when friendship starts to feel like something more.

If you’ve had past relationships where safety was missing, of course a friendship that offers that security feels extraordinary. 

But safety is just the baseline. It’s what allows you to be vulnerable, to show up authentically, to actually connect. The real question isn’t “Do I feel safe with this person?” It’s “What else is here beyond safety?” Is there mutual attraction? Reciprocity? Actual romantic possibility?

Just because someone checks the safety box doesn’t mean they check all the boxes you need for a romantic partnership. Safety gets you in the door, but it’s not the same thing as compatibility.

(6:30) The Fantasy Bubble Is Keeping You Stuck

Here’s the uncomfortable truth: it’s easy to picture a perfect relationship with someone when you’re already suspecting they’re not interested. 

You get to stay in the fantasy where everything is beautiful and uncomplicated because you’re not dealing with the messy reality of an actual relationship.

Real relationships come with logistics. They come with disagreements about how to spend holidays, different communication styles, navigating conflict, making compromises. Fantasy relationships don’t have any of that. They stay perfect in your mind because they’re not real.

As Damona explains: “You’re in the fairytale, you’re in the story that you’re writing, and you’re not popping that bubble with logistics and realities.”

And here’s what makes it even more complicated: sometimes we’re actually attracted to the impossibility. That will-they-won’t-they energy can be addictive. It’s the thrill of the chase without the vulnerability of actually being seen and chosen. Or rejected.

But staying in that fantasy keeps you emotionally unavailable to real possibilities elsewhere. 

(10:00) Before You Confess: Play Out Every Scenario

Before you tell your best friend how you feel, you need to sit with every possible outcome. Not to catastrophize, but to actually prepare yourself emotionally for what could happen next.

• Scenario one: She says she’s straight and this isn’t going anywhere. She loves your friendship, but she can’t reciprocate romantic feelings. Could you handle hearing that and still show up as her friend? Or would knowing that answer make it impossible to continue?
• Scenario two: She feels uncomfortable knowing you’ve had romantic feelings this whole time. Maybe she starts to question every moment you’ve shared, wondering if your friendship was genuine or if you were just waiting for your chance. She might pull away without even giving you closure.
• Scenario three: She’s intrigued. She hadn’t thought about you that way, but maybe she’s open to exploring it. Are you ready to navigate what it means to be someone’s first relationship with a woman? That comes with its own complexity.
• Scenario four: The fantasy. She’s been in love with you too, just waiting for you to say something. What’s the actual likelihood of this outcome compared to the others?

You need honest answers to these questions before you speak. Not to scare yourself, but to know what you’re truly willing to risk and what you’re not. And to understand that telling her might give you clarity, but it also might give you loss.

(13:00) The Cost of Staying Silent Is Higher Than You Think

Here’s what’s already happening, even without you saying anything: you’re avoiding conversations about her dating life. 

You’re not asking the questions a good friend would ask because hearing about her dates with men is too painful. You feel like you’re not being a good friend, and you’re right. The friendship you’re trying to protect is already changing.

Damona reminds us: “Not telling her doesn’t make the feelings go away, and telling her isn’t a magic pill.”

There’s also another cost: staying in this dynamic keeps you emotionally unavailable. You’re so invested in this person who might not be available to you romantically that you’re not open to meeting someone who actually could be your person. Someone who would choose you back without hesitation.

The real question isn’t whether silence protects the friendship. The real question is: what are you more afraid of? Losing the friendship, or continuing to hide and slowly losing yourself in the process?

(17:00) Create Distance Before You Decide Anything

Before making any declarations, do something that might feel counterintuitive: create space. Not forever, and not in a way you have to explain, but intentionally step back for a bit.

When you spend constant time with someone, there’s a biological and energetic exchange that happens. You start to sync up, to become almost symbiotic. That closeness can make it impossible to see clearly what’s actually there versus what you want to be there.

Distance gives you perspective. When you’re not in the thick of the friendship, when you’re not getting that regular hit of connection and intimacy, you can assess more honestly. 

Are you still obsessing when you’re apart? Do you still feel that pull? Or does it feel more situational, something that intensified because of proximity rather than genuine romantic compatibility?

Get some distance, then check in with yourself. Do you need to speak up about this? Or is this something that’s more in your head than in reality? Once you have that clarity, you’ll know what to do next

💌 Have a question about dating, relationships, or any connection that matters to you?

Damona’s ready to help.

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.

Dates & Mates has evolved beyond just romantic advice… Now we’re exploring all the relationships that shape your life: romantic partners, friendships, family dynamics, and your relationship with yourself..

📖 Ready to challenge the stories that might be holding you back in love?

Check out Damona’s book “F the Fairy Tale: Rewrite the Dating Myths and Live Your Own Love Story”  for a fresh take on modern relationships and the courage to rewrite your own love story.

You’re Managing Life Together, But Are You Actually Living It?

Have you ever felt like you and your partner have become the world’s most efficient roommates? 

You’ve got the logistics down to a science (bills paid, kids shuttled, house maintained) but somewhere along the way, you stopped being lovers and became project managers.

This week, a listener named Shelly perfectly captures what so many of us experience but rarely name out loud:

“I’m lonely in my own marriage. We’ve been together 12 years and we’re like this well-oiled machine. Kids get to practice, bills are paid, house doesn’t fall apart, but that’s it. We don’t actually talk anymore, just coordinate. Last week I realized we hadn’t had a real conversation in probably two months. When I brought it up, he was like, ‘what’s wrong? We’re good. We don’t fight.’ But I’m dying here. I miss my husband.”

Her story hits at something most couples face but few discuss: the efficiency trap that slowly replaces emotional intimacy with tactical coordination. Here’s how to recognize it, understand it, and most importantly, how to climb back out.

(3:00) The Corporate Marriage Trap

What got you here won’t get you there, and nowhere is this more true than in long-term relationships. 

Shelly and her husband have developed “badass skills” that make them incredible co-parents and co-managers. They’re like a well-run corporation, but corporations don’t cuddle.

The problem isn’t that you’re good at logistics. The problem is when logistics become your only shared language. 

“Dating is a set of learned skills, and relationship-ing is also a set of learned skills,” Damona explains. But here’s the kicker: we get relationship amnesia. We forget to practice the very skills that brought us together in the first place.

Think about it: you actively practice intimacy in the beginning because everything is new and uncertain. But once you’ve mastered the day-to-day operations, intimacy starts feeling optional instead of essential.

(5:00) Scheduling Intimacy Isn’t Unsexy (It’s Strategic)

Here’s something that might blow your mind: you need to schedule intimacy the same way you schedule soccer practice and financial conversations. And no, this doesn’t just mean putting sex on the calendar (though that works for some people… shout out to the “afternoon delight” and “Shabbos naps”).

This means carving out time where someone else handles the logistics while you focus solely on each other as a couple. “It is really hard to feel connected, feel sexy, or feel intimate when you’re thinking about all of the things on your to-do list,” Damona points out.

The homework here is powerful: think back to when you felt most seen and connected. What were the circumstances? What made you feel free? What elements can you recreate right now? 

Because when you can get specific about what you’re missing, you can fill that hole. But if you don’t know where the hole is, it just becomes quicksand.

(9:00) When “We’re Good” Means “I’m Drowning”

Things get tricky here… When Shelly brought up feeling disconnected, her husband’s response was classic: “What’s wrong? We’re good. We don’t fight.” Sound familiar?

This is the disconnect that kills relationships slowly: one person feels completely satisfied with a functional partnership while the other is starving for emotional connection. 

He didn’t know it was test day; he thought he was just showing up to class. Meanwhile, she’s been keeping a mental tally of every missed connection.

The solution isn’t avoiding this conversation (it’s having it differently). Instead of “we are disconnected,” try “I feel disconnected.” Instead of assuming mutual understanding, start from your own experience: “I want to feel closer and regain a sense of intimacy. How can we work together to change this?”

(12:00) Two Months Without a Real Conversation

Let that sink in for a moment. Two months. In a marriage. Without a real conversation.

This isn’t just busy schedules (this is an emotional drought). And the scary part is how gradually it happens. 

You look up one day and think, “Wait, how did we get so far apart?” Real conversation means sharing thoughts, feelings, dreams, fears… not just who’s picking up the milk.

The question becomes: are you willing to be brave and vulnerable with your partner to receive some bravery and vulnerability back? 

When all your interactions become transactional, you lose the emotional intimacy that makes a partnership feel like partnership. And the longer you go without meaningful connection, the harder it becomes to remember how to restart these conversations.

(14:00) Missing Someone Who’s Right Next to You

“I’m dying here. I miss my husband.” This line captures something most people feel but don’t know how to say. You miss the person you fell in love with, and they’re sleeping right next to you every night.

Loneliness in marriage can feel just as painful as loneliness when you’re single because the person you need is so close, but emotionally unreachable. It’s a sign that person-to-person connection is being replaced by role-to-role interaction.

But here’s the good news: the person you love is still in there. They’re still right there. 

Damona shares her own story of maintaining connection during physical separation, emphasizing the power of getting from the action to the emotion underneath it. 

When you can communicate how something makes you feel rather than just what you need them to do, everything shifts.

💌Got a communication question you’ve been sitting on?

Whether it’s about dating, relationships, boundaries, or what the heck to text back (Damona’s 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 isn’t just about romantic relationships anymore. It’s about the people who matter most (partners, friends, family, and you).

📖 Ready to challenge the stories that might be holding you back in love?

Check out Damona’s book “F the Fairy Tale: Rewrite the Dating Myths and Live Your Own Love Story”  for a fresh take on modern relationships and the courage to rewrite your own love story.

When Good On Paper Feels Empty Inside

You’ve done everything right. You’ve clarified your values, opened your heart to new possibilities, and even followed the three-date rule. But there you are, sitting across from someone who checks all the boxes while your heart whispers “meh.”

This week’s Dear Damona question comes from Taylor who’s wrestling with a frustration that hits so many intentional daters:

“I recently met a decent man who broadly matched my goals and values, was a good communicator, reliable, etc. I went on three dates, but each time I felt like I was dragging myself. I wasn’t excited to be with him, but I pushed through because I remembered your advice on giving it three dates when there’s no chemistry to see if it will build. Upon reflection, I’ve realized sense of humor is really important to me. If a man can’t make me laugh or at least find my jokes funny, I struggle to feel a connection. But I’m worried that I’m letting decent men slip by just because they’re not funny.”

Sound familiar? Let’s talk about what happens when compatibility meets reality, and why trusting your gut doesn’t make you too picky.

(00:05:00) The Three-Date Rule Has One Big Caveat You Might Be Missing

Here’s what most people get wrong about the three-date rule: it’s not about grinding through three painful encounters because someone told you to. The magic word here is CURIOUSITY.

If you’re feeling dread about seeing someone again, if you’re checking the clock during dinner, if you feel depleted rather than energized after spending time together, you already have your answer. 

“The three-date rule is if you are not curious about them after the third date, and you’ve given it those three dates to not only get to know them, but to also open up yourself,” Damona explains.

Because here’s the thing: you might not be fully yourself on date one either.

The rule exists to give both people space to get comfortable and reveal who they actually are. It’s not a prison sentence that forces you to power through misery in the name of being “open-minded.”

(00:14:00) Your Body Knows Before Your Brain Catches Up

Want a foolproof way to gauge connection? Do an energy check the moment each date ends. Not tomorrow, not when you get home and overthink it. Right when you get in your car or step onto the train.

Ask yourself: Do I feel more open or more closed after spending time with this person? Am I energized or completely drained? Your immediate physical response will tell you everything you need to know about compatibility.

This is exactly why our free Date Tracker tool includes space to capture these energy shifts while they’re fresh, so you can spot patterns about what types of people actually enhance your life.

Just make sure you’re not in a season of general malaise that might be clouding your judgment. If you’re feeling “blah” about work, friends, and everything else in your life, you might need a dating pause rather than a new person to fix your energy.

(00:16:00) Why Humor Isn’t Shallow (It’s Actually Genius)

Before you feel guilty about wanting someone who makes you laugh, understand what humor really reveals. 

It’s not just about entertainment. It’s a sophisticated compatibility test that shortcuts months of getting-to-know-you conversations.

Shared humor signals shared experiences, cultural understanding, and similar worldviews. When someone gets your joke, they’re showing you they speak your language on multiple levels. When they don’t, you’re discovering a fundamental disconnect.

“Humor actually demonstrates some other things that are really important in compatibility,” Damona notes. “Humor is a sign of shared experience. One of the reasons that you don’t find someone’s humor funny is because you might not be able to relate to it.”

But here’s where it gets deeper: humor is one of the few ways we show bravery in everyday life. When you tell a joke, you’re taking a social risk. When someone doesn’t acknowledge that risk or meet you where you are, it leaves you feeling exposed and disconnected.

(00:22:00) Decent Is the Bare Minimum, Not the Goal

Let’s address the guilt you’re carrying about “letting decent men slip by.” Here’s your reality check: everyone should be decent. 

Kindness, reliability, and basic communication skills aren’t special qualities that deserve a gold star. They’re the cost of entry.

You’re not being too picky when you want more than the basics. You’re recognizing that you deserve the extras, the upgrades, the things that make someone not just a match, but a match for you.

Stop normalizing decency as something to be grateful for. Start expecting it as the foundation upon which everything else gets built. The chemistry, the humor, the intellectual connection, the way they make you feel seen and understood. Those aren’t bonuses. Those are the real relationship goals.

(00:25:00) Why You Can’t Pre-Screen for Chemistry (And Should Stop Trying)

Stop trying to assess compatibility through texts, dating profiles, or even FaceTime calls. You cannot accurately judge someone’s humor, conversational skills, or chemistry until you’re face-to-face.

• That hilarious texter who goes silent in person? 
• The witty profile writer who can’t think on their feet during dinner? 
• The charming phone conversationalist who has zero physical presence? 

You’ve probably met them all.

So save yourself the false hope and get to the in-person meeting as quickly as possible. Match, maybe do one screening call, then meet within a week. Everything else is just delayed disappointment.

Trust the process: goals and values can be discussed on paper (or on screen), but to get to the other pillars of long-term compatibility from F the Fairy Tale, you have to feel someone out. And when it doesn’t feel right, don’t override your intuition with logic. Your body is giving you information that your brain can’t argue with.

💌 Have a relationship question that’s been weighing on you?

From dating dilemmas to family dynamics, friend boundaries to figuring out the right response to that confusing text, Damona wants to hear it all.

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.

Remember: Dates & Mates covers every relationship that shapes your world. Romantic partners, friendships, family connections, and most importantly, your relationship with yourself.

📝 Want to keep track of what’s working (and what’s not) in your love life?

Get your free Date Tracker at damonahoffman.com/datetracker

📖 Get a copy of Damona’s book to learn more about the Three Date Rule and how to find love successfully:

“F the Fairy Tale: Rewrite the Dating Myths and Live Your Own Love Story”

The “I Miss You” That Changed Everything

What happens when three simple words carry the weight of decades of gender norms?

This week’s Dates & Mates conversation started with one casual moment between a husband and wife that opened up something much bigger. 

When friend of the show Douglas asked his wife how a plan with an acquaintance came together and she said, “I just got a text that said ‘I miss you,’” it sparked a debate that many people, especially men, are quietly carrying.

“I told her it’s nice that women can just text ‘I miss you’ to each other because guys can’t do that,” Douglas said. “She insisted that we could. But I’m not convinced.” 

Let’s talk about what’s really stopping us from connecting and how we can start changing it.

(2:10) The Gender Divide That Silences “I Miss You”

There’s a reason it feels easier for women to say “I miss you.”

Many of us were socialized from a young age to express our emotions, nurture friendships, and use affirming language with each other. That doesn’t mean we all do it perfectly, but the cultural permission is there.

Men, on the other hand, often learn that bonding should happen through action, not vulnerability. So when a man says “I miss you,” it risks being misunderstood or even rejected.

What’s stopping many of us from deeper connection isn’t emotional incapacity. It’s social conditioning. And it’s costing people relationships they need now more than ever.

(5:45) The Friendship Recession Is Real

In the 1990s, over half of men said they had six or more close friends. By 2021, that number had dropped to 27%. Now, one in six men in the U.S. reports having zero close friends.

That’s not just sad. It’s dangerous. Because the emotional suppression that begins in childhood often turns into loneliness, anger, and disconnection later in life.

“I talk a lot about how we expect our partners to be everything: best friend, emotional confidant, romantic connection, but that’s not sustainable,” Damona says in the episode. “We need a constellation of care.”

And yes, that includes friendships.

(10:30) Yes, You Can Text First

Reaching out to an old friend or starting a new one might feel like an emotional mountain. But the first step doesn’t have to be dramatic.

Here are a few text ideas that feel real but not risky:

•  “I just passed our old spot and thought of you.”
•  “I saw something that reminded me of you. Hope you’re doing well.”
•  “It’s been too long. Want to catch up?”

You don’t need to say “I miss you” right away. But saying something is a good place to begin.

(14:45) How to Rebuild Friendship One Activity at a Time

If you’re someone who struggles with staying in touch or you know a friend who does, don’t wait for the perfect moment. Set up a recurring one.

Regular rituals take the pressure off vulnerability. A monthly lunch, a standing game night, even shared fandom over a sports team can become your bridge back to connection.

“It doesn’t have to be deep to be meaningful,” Damona shares. “You’re just giving the friendship a place to live.”

Even one standing plan can shift how connected you feel and how safe it becomes to say more next time.

(20:00) The New Friendship Playbook

Connection isn’t gendered. And real friendship doesn’t come from grand gestures. It comes from small acts of courage over time.

So if you’ve been telling yourself you can’t say how you feel, or you’re too old to make new friends, or it’s too awkward to reach out, here’s your reframe:

You can. You’re not. And it isn’t.

Try something this week. Make a list of people you’d like to reconnect with. Or notice the folks you cross paths with regularly and take the first step. Ask a question. Make a comment. Be curious.

Sometimes all it takes is a little reminder that you matter to someone and that they matter to you.

💌 Got a communication question you’ve been sitting on?

Whether it’s about dating, relationships, boundaries, or what the heck to text back… Damona’s 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 isn’t just about romantic relationships anymore. It’s about the people who matter most: partners, friends, family, and you.

📝 Want a better way to track what’s working (and what’s not) in your love life?

Get your free Date Tracker at damonahoffman.com/datetracker