dating drama young an old🩷Riley
by Riley
Welcome to Dating Drama Young & Old, where we dive into the real stories behind love, heartbreak, dating, and starting over/.From the excitement of new connections to the frustrations of ghosting, red flags, divorce, and finding love again, we explore the challenges faced by daters of all ages/. Whether you’re young and navigating today’s dating world or over 50 and rebuilding your life after heartbreak, this podcast brings honest conversations, real/-life experiences, and lessons learned along the way/.Join us for stories that will make you laugh, think, and maybe even see your own dating
Episodes
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MONDAY’S BIG EPISODE DELAYED! 💔 YOU WANT COMPANIONSHIP… SO WHY DO YOU FREEZE? TONIGHT WITH RILEY!
Hey everybody! Today’s big Monday episode of Dating Drama Young & Old is delayed until tonight because work called, but you won’t want to miss this one! We’re talking about COMPANIONSHIP! Why do people say they’re lonely and want somebody special, but when someone comes along who wants to build...
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Too Lonely for Love, or Too Busy to Make Time?
Got two minutes? Let’s talk! Everyone says they want companionship, but are we really willing to make time for someone special? This is a two-minute sneak peek at what we’re discussing in our full episode on Monday! 💚 PLUS, A CHANCE TO WIN! Participate in our Spotify poll for a chance to win a...
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1 min clip thankful or not?
Did you say thank you to anyone today, and are you thankful for them, and do you feel blessed, or are you that person that doesn’t think you owe them a thanks, and you just take it for granted? Tell me what you think.
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Are You Thankful or Do You Take Things for Granted?
Sometimes life gets so busy that we forget to appreciate the little things and the people who make a difference in our lives. In tonight’s episode of Dating Drama Young & Old, Riley talks about being thankful, showing gratitude, and asking ourselves an important question: Are we truly thankful…
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Sassy ASMR Tease | Candlelight, Quiet Nights & a Heavy Heart
Sometimes life gets overwhelming, and all we need is a little peace, a soft voice, and a moment to ourselves. Tonight, Riley invites you into a quiet, intimate moment of candlelight, relaxation, and gentle ASMR. No pressure, no expectations, just a little comfort for the heart and soul. Even a...
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Thankful, Blessed & Boiling Over
Join Riley in the kitchen for an unscripted conversation for the 40-and-up crowd about being thankful for the little things and the big blessings—even when the eggs boil over! I’m talking about dating myself, keeping my standards high, and staying open to love without giving up my morals and...
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Thankful for the Big and Little Blessings
Sometimes the biggest blessings are the people who show up, and the little ones are the moments that help us through the day. Tonight, I’m talking about gratitude, love, loss, and finding something to be thankful for even when your heart is hurting. From a warm cup of coffee to someone reminding...
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Halloween Magic: From Heartache to Joy 🎃🧡
After a sad visit with my sister Linda, an unexpected stop at a Halloween house on Olympic Drive brought joy to my heart. I meet the family behind the magic and hear what makes all their work worthwhile—the kids! Come along for costumes, decorations, and a little happiness when I needed it most....
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The Me an we lost!
The Me and We Lost Sometimes life takes us down roads we never expected. Along the way, we leave behind dreams, passions, talents, and sometimes even people we wish we’d held on to. Come spend 10 minutes with Riley as we talk about the things we lost along the way and the parts of ourselves we’d...
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Getting Spooky with Riley… Just the Beginning\! Guys, don’t miss this one
Guys, don’t miss this one—your girl is getting ready to get spooky! Come spend 10 minutes with me as I work on my Halloween dress and let you peek at the fun in the making. We’re chatting about Dating Drama, Young & Old and Dating Drama with a Kick, and I want to know what YOU enjoy seeing on my...
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Pick up my day in the park🍁
Come spend a few quiet minutes with me in the park. Just me, the autumn leaves, and a little conversation along the way. A peaceful peek into my day—sometimes a little time alone is exactly what we need. 🍂 Riley
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2min tease buried desires
Sometimes two minutes is just enough to make you curious. 😉 Here’s a little taste of “Buried Desires” for my Dating Drama, Young & Old listeners. If you’ve wanted a closer peek into my life—the deeper details and a little more spice—the full story is waiting on Dating Drama with a Kick. Come get...
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Desires You Buried
What did you want before everybody told you who to be? Behind the responsibilities, the relationships, and everybody else’s opinions, there may still be a little fire you never stopped feeling. That poem you wrote at 12. That art you hid away. That dream you were told was “just a hobby.” Today on...
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Moonlit Magic 🔥 A Cozy Autumn Night with Riley
Come sit by the fire with me. 🔥 The moon was showing off, the autumn air was crisp, and there was chili, brownies, and good company. It was one of those nights that just felt good, and I wanted to share a little of that happiness with you. Enjoy the firelight, the music, and a cozy fall moment...
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The mystery plans change. Did you hide your desire's away?
Sometimes we let others tell us what we should and shouldn’t do with our lives, our careers, our family, our friends, our dating relationships. Sometimes we lose desires that we wanted when we were younger because of family or even parents say, that’s not a career, that’s a hobby but do you ever...
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Young man, karaoke, kissers
Hot young men, karaoke kisses, and a little sunshine—come spend some time with Riley! 💋 I’m having my protein and sharing memories, everyday life, and whatever’s on my sassy mind. Would you sing me a song or lean in for a kiss? 😉
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Sassy sunshine Five minute tease of ASMR too, please
A little sunshine, a little sass, and five minutes of ASMR with yours truly. Come unwind with Riley—it’s just a little tease to brighten your day. ☀️💋
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Surprise picture for you (NO)
You say you wanna get to know me. You’re already making plans to come see me. But hold on—why are you sending me a picture I already told you I didn’t want? I’m 65, and I’ve got questions. What the hell happened to talking first? It’s Riley, and we’re talking about those unwanted pictures and why...
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I said no depict anyway🍆
You’re chatting, getting to know someone, and you’ve already said NO to explicit pictures. Then you wake up to a dick pic. I sent a smiling selfie—not permission. Today on Dating Drama, Young and Old, we’re talking dating in your 20s and 30s, unwanted pictures, and boundaries. Why flirt if you...
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ASMR will take your breath away!!
Long day at work then to the shopping center then the park is beautiful. The water was splashing against the rocks little flooded. The geese were everywhere. They were surprising airplanes in the background. People fishing is a beautiful afternoon and I want to share it with you.
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New chat new love the delivered
A new chat, a little flirting, and suddenly it’s “love” and “baby doll.” You’re smiling at your phone, getting excited, making plans, and thinking this could actually go somewhere. Then your message sits on delivered. The date never happens. Now you’re ghosted, brokenhearted, and wondering what…
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3 mini tease chatting then delivered🤬
Three minutes of real talk about chatting, being left on delivered, and knowing when to walk away. You’re trying to build a connection—but are they giving you a conversation or just keeping you waiting? And when the talk crosses your boundaries, you don’t have to stay and entertain it. A little...
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Sassy Lips—You Want WHAT? 💋
Coffee’s hot, and apparently your thoughts are getting hotter. I’m trying to get to know you, and you’re trying to get me to talk naughty before we’ve even planned a date. Honey, you disappear for 12 hours and come back expecting the spicy version of me? Get your conversation warmed up first. ☕💋
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Married, what are you cheating? Two minutes of full episode
Married, why are you cheating? Marriage begins with butterflies, promises, and "till death do us part." But what happens when everyday life settles in and someone starts looking elsewhere? Riley talks honestl
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Connection takes more than conversation🗣️
We’re over 40, and we still want someone to sit down with, talk to, and feel close to. But you can talk for hours and still not know where you stand. I’m talking about making time, listening to each other, and figuring out whether there’s a real connection—or you’re just filling an empty spot…
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Filling In for Another Woman
When you spend three weeks building a connection—sharing time, laughter, and support—then they go back to somebody else, where does that leave you? Were you a companion, a friend, or just filling in for another woman? Today on Dating Drama, Young and Old, we’re talking dating in your 20s and 30s,...
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Water, Whimsy & Halloween ASMR — Part Two
Come walk with Riley for the final seven minutes of our nature adventure. Enjoy flowing water, splashing fish, a little conversation with a squirrel, and beautiful musical chimes in the children’s play area. We’ll pause for some cute Halloween jokes before a quiet goodbye as I walk out of the…
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Quiet Water, Come With Me — Part One
Come walk the path with me for seven minutes of quiet nature ASMR. Watch the fish splash and swim, listen to the waterfall, and enjoy a little peaceful time together. This is just the beginning—our walk continues in Part Two! Due to technical difficulties, I’ve had to split this episode into two...
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Sexy Strolls and Spooky Surprises 🎃🌿
Come wander with me, baby! 🌿🎃 Twenty minutes of beautiful gardens, colorful flowers, fascinating plants, fish, and playful Halloween surprises. I’m taking you along for my arboretum adventure—with a little sass, plenty of curiosity, and beautiful spots that would make the sweetest date. Who…
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Married, why are you cheating?
Marriage begins with butterflies, promises, and “till death do us part.” But what happens when everyday life settles in and someone starts looking elsewhere? Riley talks honestly about fading excitement, broken trust, and what commitment means when temptation shows up. You’re married—why are you...
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Five minute tease when the butterflies disappear
The butterflies. The tingles. The wedding vows. You swear you’ll love each other forever—but what happens when babies, bills, work, and everyday life take over? When the excitement fades, do you choose your marriage or chase butterflies somewhere else? Please push the follow🩷
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Sassy: Marriage Beyond the Vows
Some of us who are older need this conversation, too. Because today, I want to talk about marriage. About commitment. About what happens after you say those words: for better or
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ASMR a touch of fire
Nice fire outside with sizzling and crackling And outside natural sounds around us sounds of voices enjoying the fire
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Sweet and kind gentleman talks
Sweet, kind, and honest—yes, real gentlemen are out there! Join Riley on Dating Drama, Young and Old as Micheall shares his 10 rules of being a gentleman, and other men add their thoughts on respect, kindness, and treating people right. A little charm, some honest conversation, and a question for...
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Social butterflies across the ages
From 20 to 80, we’re talking charm, flirting, and what happens when that social butterfly doesn’t show up. Can a social butterfly also be a gentleman? Join Riley on Dating Drama, Young and Old as we bridge into Saturday’s “10 Rules of a Gentleman.” What does a gentleman look like to you?
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Social butterfly after 40
Absolutely nothing wrong with being a social butterfly even when you’re older it just looks a little different. We’re more about connections and concerns about other people bringing them together or maybe we are the one that likes to go to different places but we don’t leave somebody in the…
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Shocking, surprise where the butterfly lands
Where the Butterfly Lands Lands He called himself a social butterfly and was excited to share his dating story on my podcast. We talked about it all week. Then he said he’d come by after an errand, never showed up, and read my messages without answering. Was something going on, or did he simply...
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Muffin and tox and lavender surprise
Come into my kitchen for a little muffin talk while I show you my oven and make lavender oil. Then it’s time to settle in for a soothing lavender massage… but I stop the video just as the massage begins. A little surprise for you at the end. 💜
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The talks worth having
Some conversations deserve more than a quick answer. In this 28-minute episode of Dating Drama, Young and Old, Riley makes room for the bigger talks—the ones about dating, heartbreak, healing, and what we really need from each other. Come sit with me. This conversation is worth our time.
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The Rebound Bridge: Ages 20 to 80
This Friday, Riley brings the whole week together. Whether you’re 20 or 80, a breakup can leave you reaching for comfort, attention, or someone new. Younger and older adults may date differently, but the hurt underneath can feel familiar. Let’s talk about rebounds, what we’re hoping they’ll fix,...
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What rebound over 40 looks like!
A rebound after 40 can look different. You may be coming out of a long marriage, grieving someone you lost, or trying to find yourself after your whole life changed. The dating pool feels smaller, and you know more about what you want—but you can still rush toward someone because you miss feeling...
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IS REBOUND SEX WORTH IT?
It’s about whether rebound sex actually helps you heal—or whether you need to give yourself time before jumping into someone new.
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MY PAIN, YOUR PEACE — ASMR 🩷
Tonight, you’re seeing me in a vulnerable moment—with my broken wrist, this painful cast, and a heart carrying more than most people can see. Between the pain in my hand, the pain surrounding my sister, and the heaviness in my heart, life has hurt lately. But pain will not stop me. I promised you...
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Meet me on the bridge🌉🩷
Young, older, and everyone in between—tonight, we meet on the bridge. We’re bringing two generations together to talk about dating, changing yourself for love, sex, acceptance, and what it takes to understand one another. Real men gave anonymous answers, and I’m responding honestly. Can we stop...
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Would You Change Her?
A two-minute tease from tomorrow’s powerful 37-minute podcast. One man would love her exactly as she is. Another says if she doesn’t enjoy sex, it won’t work. But what did I say? You’ll have to come back tomorrow to find out. 🍉🔥
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ASMR rain n light tease
A little ASMR tease with soothing rain and calming lights—just a taste of the full storm coming Saturday morning. 🌧️✨
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The Bridge Starts Here 3 min teaser!
Just a three-minute tease for something BIG coming Saturday morning. Raw, real, and straight from my heart. The bridge starts here. 🎙️💚
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ASMR rain and thunder, short tease🌧️
A brief, soothing rainstorm with soft thunder rumbling in the distance—perfect for a peaceful ASMR break. Something stormy is stirring tonight, and I’m letting the gentle rain draw me in. Want to hear more calming storm sounds? Follow me on Spotify. 🌧️⛈️
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Step outside your comfort zone
Being over 40 doesn’t mean your adventurous years are behind you. Sometimes stepping outside your comfort zone is exactly how you rediscover your confidence, excitement, and who you really are. What would you try if fear weren’t holding you back?
About this show
Welcome to Dating Drama Young & Old, where we dive into the real stories behind love, heartbreak, dating, and starting over/.From the excitement of new connections to the frustrations of ghosting, red flags, divorce, and finding love again, we explore the challenges faced by daters of all ages/. Whether you’re young and navigating today’s dating world or over 50 and rebuilding your life after heartbreak, this podcast brings honest conversations, real/-life experiences, and lessons learned along the way/.Join us for stories that will make you laugh, think, and maybe even see your own dating
Hosted by
Riley
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