Today, we’re visted by one of our favorite. Ilana Dunn Solomon—dating coach, content creator, and the voice behind Seeing Other People, a podcast that’s basically the internet’s wisest, funniest older sister. Ilana’s known for cutting through the noise of modern dating with raw honesty, zero judgment, and the kind of insights that make you feel both called out and comforted.But today, she’s not here alone. She brought backup—her husband, Jake Solomon. The man who went from first date to fiancé to full-on husband in a love story that has unfolded both publicly and privately, with all the chaos, clarity, and chemistry that comes with it.In this episode, we’re diving into all of the hilarious, and deeply human moments that makes a marriage. We’re talking about the difference between butterflies and real compatibility, and the myths people still believe about love.We're also talking dating app burnout, emotional availability, male perspectives, green flags, and everything that comes up when a dating expert marries someone who perhaps never expected to be part of the discourse...00:00 - Intro: Welcome Alana & Jake00:36 - How They Met: A Hinge Love Story02:02 - The Early Stages of Dating03:26 - First Impressions on Their First Date05:05 - COVID Dating & Timing06:22 - Was Dating a Dating Coach Intimidating?07:42 - Launching Seeing Other People08:24 - The Engagement Story10:49 - When She Knew He Was "The One"12:26 - Married Life & Moving In Together13:38 - Living Together Adjustments15:08 - The Great Sock Debate16:32 - Family Dynamics & Holidays18:57 - Marriage Myths That Aren’t True20:09 - Dating Your Partner After Marriage21:04 - Their Best & Worst Dates24:43 - Newlywed Game: He Said / She Said31:24 - Dating Advice Men & Women Need to Hear32:59 - The Dating App Feature They Wish Existed34:39 - Are Nice Guys Out?36:16 - Why Aren’t More Men at Singles Events?39:09 - The Fear of Rejection in Dating40:23 - Are We Obsessed With Being Chosen?43:30 - Advice for Burned-Out Daters45:26 - Managing Dating Expectations47:01 - Their Own First Dates Reflection48:09 - How Well Do You Know Each Other? Quiz50:27 - Closing & Final ThoughtsNew episodes every Monday. Subscribe for more real talk on dating, relationships, and everything in between.If you’re loving the conversation, hit that like button, drop a comment with your thoughts, and hit subscribe for more unfiltered dating talk on First Round’s on Me!Download FROM: https://firstroundsonme.coInstagram: / firstroundsonmeTikTok: / firstroundsonmeappJoe:https://www.instagram.com/firstroundsonjoe/Hannah :https://www.instagram.com/hannah_glasby/Exclusive Offer - Transform Your Dating Life Today!Say goodbye to swiping left and hello to real connections! First Round’s On Me helps you skip the awkward stages and find meaningful matches. Get a FREE month of FROM’s premium subscription—all you have to do is use our code DATING!

In this episode, we pull back the curtain on modern dating and unpack the theories shaping today’s romantic landscape. From proximity crushes and delayed disappointment to the 72-hour rule and "plans are the new foreplay," Joe and Hannah break down the traps, myths, and hard truths of dating apps and digital romance. Why does texting build false intimacy? Are we addicted to the fantasy of perfection? And how does taking charge become the ultimate sign of emotional maturity? Tune in for raw takes, real stories, and honest conversation about what it takes to build true connection in today's swipe-heavy world.00:00 - Introduction: Breaking Down Dating Theories00:30 - Proximity Crush Theory02:00 - Real-Life Example: The F45 Instructor Story05:00 - The Impact of Fantasy & False Intimacy07:00 - Delayed Disappointment & Table Theory09:00 - The Dangers of Endless Texting11:00 - Fear of Rejection & Addiction to Perfection14:00 - Why True Intimacy Requires Vulnerability15:00 - The 72-Hour Rule Debate20:00 - How Many People Should You Date at Once?25:00 - Intentionality vs. Oversaturation26:30 - Plans Are the New Foreplay: Why Effort Is Sexy29:00 - Emotional Maturity & Taking the Lead30:00 - Closing Thoughts & TakeawaysNew episodes every Monday. Subscribe for more real talk on dating, relationships, and everything in between.If you’re loving the conversation, hit that like button, drop a comment with your thoughts, and hit subscribe for more unfiltered dating talk on First Round’s on Me!Download FROM: https://firstroundsonme.coInstagram: / firstroundsonmeTikTok: / firstroundsonmeappJoe:https://www.instagram.com/firstroundsonjoe/Hannah :https://www.instagram.com/hannah_glasby/Exclusive Offer - Transform Your Dating Life Today!Say goodbye to swiping left and hello to real connections! First Round’s On Me helps you skip the awkward stages and find meaningful matches. Get a FREE month of FROM’s Terracotta premium subscription—all you have to do is use our code DATING!

On this episode of First Round’s On Me, we sit down with the brilliant and brutally honest content creator Greyson Hoelzel. From engineering by day to viral TikToks by night, Grayson opens up about building a following, the trials of modern dating, and why he has beef with Disney adults. Expect dating hot takes, a round of “How Well Do You Know Yourself?”, and raw insight into navigating life, love, and internet fame—all with a side of humor.🎧 New episodes every Monday. Subscribe for more real talk on dating, relationships, and everything in between.Chapters:00:00 – Cold open: “Disney adults shouldn't have kids?”00:20 – Intro: Meet Greyson01:08 – Playing it cool: Managing expectations02:13 – Who is Greyson?03:27 – Dating in Idaho (and the ring-check habit)05:07 – Fry sauce and East Coast culture shock05:45 – Becoming a content creator07:02 – Viral moment: The micropenis video08:12 – Balancing engineering and content08:59 – Creative process & idea generation10:19 – TikTok nerves and staying authentic11:12 – Editing philosophy: Keep it raw12:34 – Being yourself on camera13:16 – Advice for new creators14:38 – Game: “How Well Do You Know Yourself?”22:29 – Dating status & moving to NYC24:19 – The invisible wall in relationships26:31 – Fix vs. evolve: A therapy conversation28:30 – Red flags that are... hot?30:05 – Threesomes, boundaries, and bisexuality31:44 – Dating rule to retire: The 3-month myth33:21 – Dating apps, options fatigue, and emotional elbow grease36:15 – The paradox of too many choices38:05 – Should you be able to review your date?40:40 – Who should pay on the first date?43:12 – Random green flag: Passionate rants44:06 – Dating hill to die on: Anti-Disney adults47:27 – Final green flag: Genuine kindness48:57 – Game: “What Would Greyson Do?”If you’re loving the conversation, hit that like button, drop a comment with your thoughts, and hit subscribe for more unfiltered dating talk on First Round’s on Me! Download FROM: https://firstroundsonme.co Instagram: / firstroundsonme TikTok: / firstroundsonmeapp Joe: https://www.instagram.com/firstroundsonjoe/Hannah : https://www.instagram.com/hannah_glasby/Exclusive Offer - Transform Your Dating Life Today! Say goodbye to swiping left and hello to real connections! First Round’s On Me helps you skip the awkward stages and find meaningful matches. Get a FREE month of FROM’s Terracotta premium subscription—all you have to do is use our code DATING!Promo Code - DATINGLink - https://from.onelink.me/LQvW/from