Jackie Shames, friend and co-host of Fill Your Cup is back to chat all things confidence, learning from past relationships, and staying true to who you are. Jackie shares her experiences dating between Miami and New York, how the seasons have been impacting her dating life, and the challenges of balancing personal and professional life. We discuss the the New York influencer scene, friendship dynamics, and podcasting, and we live-text someone Jackie went on a date with.00:00 - 09:30 Navigating Confidence and Dating09:30 - 26:24 Unexpected Encounters26:24 - 28:54 Reflecting on Closure and Moving On28:54 - 29:49 The Importance of Detachment29:49 - 31:25 Running Into an Ex-Fling31:25 - 33:24 Finding Security in a New Relationship33:24 - 36:26 Navigating Dating Patterns and Self-Sabotage36:26 - 43:38 Balancing Personalities in Relationships43:38 - 55:53 Influencer Culture and Personal GrowthSay goodbye to your anxiety and say hello to relaxation with Sunset Lake CBD. Head to https://sunsetlakecbd.com/coupon/sop and use code SOP for 20% off your order.  Spark something uncommon this holiday season and get 15% off the right gifts from Uncommon Goods at uncommongoods.com/sop Treat yourself and your loved ones to spa-quality skincare essentials that deliver a moisture-rich glow. Use code seeingotherpeople for 15% off at oakessentials.comTackle your toughest days by microdosing with Schedule 35 and get 15% off with code SOP at schedule35.co So, if you’re looking for a thoughtful and practical gift that he’ll actually use and love, The Chairman™ Pro is the way to go! Get 20% off + free shipping on The Chairman & with the code SOP at Manscaped.com Learn more about your ad choices. Visit megaphone.fm/adchoices

Bethany and Walter share their heartwarming real-life journey of meeting on an app and building a relationship over the past 1.5 years. They delve into their initial dating struggles, including catfishing and ghosting, and their eventual connection that sparked over a phone call and FaceTime. The couple discusses the importance of open communication, handling financial changes, how they support each other in tough times. Walter and Bethany explore their compatibility, different upbringings, and expectations in their relationship, and provide advice to singles ready to give up on dating."Love hearing how people found love? Check out this playlist filled with stories of how real daters met their person!Say goodbye to your anxiety and say hello to relaxation with Sunset Lake CBD. Head to https://sunsetlakecbd.com/coupon/sop and use code SOP for 20% off your order.  Spark something uncommon this holiday season and get 15% off the right gifts from Uncommon Goods at uncommongoods.com/sop Treat yourself and your loved ones to spa-quality skincare essentials that deliver a moisture-rich glow. Use code seeingotherpeople for 15% off at oakessentials.comTackle your toughest days by microdosing with Schedule 35 and get 15% off with code SOP at schedule35.co So, if you’re looking for a thoughtful and practical gift that he’ll actually use and love, The Chairman™ Pro is the way to go! Get 20% off + free shipping on The Chairman & with the code SOP at Manscaped.com. Learn more about your ad choices. Visit megaphone.fm/adchoices

Felix Levine, entrepreneur and host of Unlike Me, joins the show to discuss his journey in podcasting, the dynamics of his relationship with Serena Kerrigan, and his personal growth. Felix and Ilana delve into why he started his podcast during a challenging time in college and the lessons learned from interviewing successful individuals. Felix shares insights on the importance of genuine connections, handling past relationship traumas, and the intricacies of dating someone significantly older. The episode also addresses listener questions on unique dating challenges and offers advice on maintaining relationships amidst personal anxieties.01:35 - 03:40 Navigating College and Depression03:40 - 04:32 Podcasting as a Career04:32 - 06:10 The Realities of Podcasting06:10 - 08:18 Maturity and Personal Growth08:18 - 11:06 Friendships and Ambition11:06 - 14:03 A Special Relationship14:03 - 15:02 The Meet Cute and Beyond15:02 - 25:15 Dating Advice and Personal Stories25:15 - 27:58Confident Beginnings27:58 - 30:59 Overcoming Past Trauma30:59 - 34:46 Healing and Moving Forward34:46 - 41:29 Navigating Age Gaps in Relationships41:29 - 48:32 Listener Questions: Weird and Serious48:32 - 51:10Best Dating Advice51:10 - 53:29 OutroNeed more of the guys’ perspective? This playlist has all SOP episodes with male guests!Say goodbye to your anxiety and say hello to relaxation with Sunset Lake CBD. Head to https://sunsetlakecbd.com/coupon/sop and use code SOP for 20% off your order.  Spark something uncommon this holiday season and get 15% off the right gifts from Uncommon Goods at uncommongoods.com/sop Treat yourself and your loved ones to spa-quality skincare essentials that deliver a moisture-rich glow. Use code seeingotherpeople for 15% off at oakessentials.comTackle your toughest days by microdosing with Schedule 35 and get 15% off with code SOP at schedule35.co So, if you’re looking for a thoughtful and practical gift that he’ll actually use and love, The Chairman™ Pro is the way to go! Get 20% off + free shipping on The Chairman & with the code SOP at Manscaped.com. Learn more about your ad choices. Visit megaphone.fm/adchoices

Harry returns to the show after two years to discuss his life journey, highlighting the lessons learned from navigating singlehood, personal growth, and embracing new passions like photography. Throughout the conversation, they explore Harry's experiences with dating, the societal pressures of relationships, and his journey to understand and accept his neurodiversity. The episode emphasizes making one's own rules in life, finding personal fulfillment through community, and the transformative power of genuine human connections.Give your brain a boost with Fungies functional mushroom gummies! Head to eatfungies.com and enjoy free shipping and 20% off with code SOP. Say goodbye to your anxiety and say hello to relaxation with Sunset Lake CBD. Head to https://sunsetlakecbd.com/coupon/sop and use code SOP for 20% off your order. Pro tip: try their sleep gummies! Grow your business, no matter what stage you’re in. Sign up for a #1 per month trial period at shopify.com/seeingotherpeople! Learn more about your ad choices. Visit megaphone.fm/adchoices

In this episode, Rebekah Lipsky, a therapist specializing in major life transitions, joins us to share her personal experience of calling off her engagement and wedding after a five-and-a-half-year relationship. She delves into the emotional challenges of such decisions, the importance of aligning one's values, and her journey of self-discovery post-breakup. The discussion includes insights on handling grief, the role of supportive friends, and her upcoming support group for women who have called off engagements. Rebecca also offers valuable advice for anyone facing similar life transitions.Follow Rebekah on Instagram at @reflectwithrebekah and inquire to work with her at www.rebekahlipskycounseling.com/ 04:41 - 06:34 Life Transitions and Personal Struggles06:34 - 09:45 Calling Off her Engagement09:45 - 15:21 The Emotional Rollercoaster15:21 - 27:48 Making the Tough Decision27:48 - 28:24 Facing the Guilt of Canceling a Wedding28:24 - 29:56 Support from Friends and Family29:56 - 33:01 Layers of Grief in Breakups33:01 - 38:14 Supporting Friends Through Breakups38:14 - 45:10 Rediscovering Yourself After a Breakup45:10 - 48:39 Navigating Relationship DecisionsGive your brain a boost with Fungies functional mushroom gummies! Head to eatfungies.com and enjoy free shipping and 20% off with code SOP. Say goodbye to your anxiety and say hello to relaxation with Sunset Lake CBD. Head to https://sunsetlakecbd.com/coupon/sop and use code SOP for 20% off your order. Pro tip: try their sleep gummies! Grow your business, no matter what stage you’re in. Sign up for a #1 per month trial period at shopify.com/seeingotherpeople! Learn more about your ad choices. Visit megaphone.fm/adchoices

Adrian, a self-identified 27-year-old male nerd from Canberra, Australia, shares his experiences and insights on dating, offering a male perspective. He discusses his dating history, including early high school relationships and the impact of a serious breakup at age 18. Adrian explains his cautious approach to dating apps and reflects on the challenges of dating as an introvert. He emphasizes the importance of taking risks in dating, inspired by a quote from the movie 'We Bought a Zoo.' Adrian also addresses the common dating adage 'if he wanted to, he would' and shares his thoughts on modern dating pressures and misconceptions.Give your brain a boost with Fungies functional mushroom gummies! Head to eatfungies.com and enjoy free shipping and 20% off with code SOP. Say goodbye to your anxiety and say hello to relaxation with Sunset Lake CBD. Head to https://sunsetlakecbd.com/coupon/sop and use code SOP for 20% off your order. Pro tip: try their sleep gummies! Grow your business, no matter what stage you’re in. Sign up for a #1 per month trial period at shopify.com/seeingotherpeople! Learn more about your ad choices. Visit megaphone.fm/adchoices

The incredible Suzy Welch joins us today to discuss how uncovering your values can help you find and build lasting relationships. Suzy is a public speaker, author, and professor of NYU's infamous "Becoming You" course. Suzy shares her journey of self-discovery through her 'Becoming You' methodology along with her life-changing decision making method 10-10-10 (yes, you can apply it to making decisions in dating!)We discuss the potential impacts of value misalignment in relationships, and how understanding of one's values can inform personal and professional life decisions, leading to greater fulfillment.Follow Suzy on Instagram @suzywelch and check out the Becoming You podcast on Spotify.03:34 - 03:34 The Concept of Values and Their Importance03:54 - 07:12 Developing the 'Becoming You' Methodology07:12 - 08:28 Values in Relationships and Personal Growth08:28 - 14:15 The Values Bridge Tool and Its Applications24:19 - 26:03 High Scope vs. Low Scope Values in Relationships26:03 - 30:06 Work Centrism: Balancing Career and Family30:06 - 37:28 The 10-10-10 Decision-Making Method37:28 - 41:47 The Velvet Coffin: Avoiding Complacency41:47 - 46:19 Whose Life Do You Want Anyway?Give your brain a boost with Fungies functional mushroom gummies! Head to eatfungies.com and enjoy free shipping and 20% off with code SOP. Say goodbye to your anxiety and say hello to relaxation with Sunset Lake CBD. Head to https://sunsetlakecbd.com/coupon/sop and use code SOP for 20% off your order. Pro tip: try their sleep gummies! Grow your business, no matter what stage you’re in. Sign up for a #1 per month trial period at shopify.com/seeingotherpeople! Learn more about your ad choices. Visit megaphone.fm/adchoices

Brandon shares his story of how his marriage to the love of his life ended in divorce. He opens up about his growth and healing journey post-divorce, and what it was like to reenter the dating world as a man in his early 30s who hadn’t dated someone new since 2010. Brandon shares how he has since moved halfway across the country and started a new job while navigating the complexities of modern dating. Tune in for a conversation where we explore relationship dynamics and discuss the importance of self-awareness and patience.Give your brain a boost with Fungies functional mushroom gummies! Head to eatfungies.com and enjoy free shipping and 20% off with code SOP. Say goodbye to your anxiety and say hello to relaxation with Sunset Lake CBD. Head to https://sunsetlakecbd.com/coupon/sop and use code SOP for 20% off your order. Pro tip: try their sleep gummies! Grow your business, no matter what stage you’re in. Sign up for a #1 per month trial period at shopify.com/seeingotherpeople! Learn more about your ad choices. Visit megaphone.fm/adchoices

Gab Saper, a personal stylist passionate about body acceptance, shares her journey from childhood camp romance to a rekindled love story in New York. She discusses the influence of fashion on dating, advocating for dressing authentically to enhance self-confidence rather than conforming to toxic beauty standards. Gab emphasizes the importance of comfort in clothing choices, dives into the emotional ups and downs of modern relationships, and shares tips on curating a wardrobe that expresses individuality and supports genuine connections.

In this warm and engaging episode, Ilana welcomes her parents, Barbara and Chuck, to share their charming courtship story, personal insights on love and marriage, and how they met on a hot summer night at an Israeli bond fundraiser. Reflecting on their journey together, they discuss relationship dynamics, parenting, and the evolving landscape of dating from their pre-internet days to the present. They offer valuable advice on navigating the modern dating world, staying hopeful, and the importance of being true to oneself in love. The episode also touches upon Ilana's recent wedding planning experience and fond family memories, making it a heartfelt exploration of love across generations.00:00 Introduction and Welcoming Parents00:11 First Impressions and Initial Reactions01:10 How They Met: A Love Story05:53 Navigating Early Relationship Challenges17:58 The Proposal and Engagement21:45 Adapting to Life Changes and Parenthood24:36 Balancing Personal Interests and Family Life26:41 A Memorable Vegas Trip28:33 Lost and Found Wallets29:13 Listener Questions: Favorite Nephew30:41 Advice for Single Women33:45 Reflecting on Love and Relationships39:18 Alana's Career Journey47:41 Wedding Planning Insights51:50 Final Thoughts and AdviceGive your brain a boost with Fungies functional mushroom gummies! Head to eatfungies.com and enjoy free shipping and 20% off with code SOP. Say goodbye to your anxiety and say hello to relaxation with Sunset Lake CBD. Head to https://sunsetlakecbd.com/coupon/sop and use code SOP for 20% off your order. Pro tip: try their sleep gummies! Grow your business, no matter what stage you’re in. Sign up for a #1 per month trial period at shopify.com/seeingotherpeople! Learn more about your ad choices. Visit megaphone.fm/adchoices