The Year of Dating Yourself: How One Woman Chose Herself — and Changed Everything | Abby Rosmarin
What happens when you stop looking for love and start finding yourself? In this episode, Jennifer sits down with author and New Hampshire transplant Abby Rosmarin in Concord, NH, to talk about the year that changed her life: 2023, the Year of Dating Herself.
After a string of tumultuous relationships that left her gaslit, depleted, and sitting in a bathtub wondering how she got there, Abby made a radical decision — to spend an entire year intentionally single, intentionally present, and intentionally devoted to her own company. The result? A healing journey she never could have predicted, a book, and a relationship she never knew was possible.
From solo concerts and dining alone for the first time to impulsive ear piercings and sunrise coffee dates by the lake, Abby shares the raw, funny, and deeply human story of what it looks like to truly date yourself — awkwardness, check-engine-light moments, and all. She and Jennifer also dive into the pressures women face around singlehood, the power of therapy and self-reflection, codependency and healing, and what it really means to show up for yourself before you can fully show up for anyone else.
📍This episode was recorded in Concord, New Hampshire.
MEET ABBY ROSMARIN
Abby Rosmarin is the author of The Year of Dating Myself: How My Solo Tour Healed More Than Just My Heartbreak. Her work has been featured in the Huffington Post, Bustle, the Bangalore Review, and others.
CONNECT WITH ABBY
KEY TAKEAWAYS
- Your story doesn’t start in a vacuum. The patterns in our adult relationships almost always trace back further than we think. Recognizing those echoes, without shame, is the first step toward changing them.
- Dating yourself is an act of intention, not circumstance. Abby didn’t just “be single”, she committed to a structured, year-long practice of taking herself out, showing up for herself, and treating her own company as something worth investing in.
- Self-care doesn’t have to be grand. Some of Abby’s most meaningful moments were a $5 coffee and a sunrise at the lake. Romanticizing the small things is a skill and a gift you can give yourself any day.
- You’re not being watched as closely as you think. One of the most liberating lessons of solo adventures? Nobody is paying as much attention to you as your anxiety says they are. Do the thing anyway.
- Codependency is quiet — until it isn’t. Abby reflects on how deeply her sense of identity had become wrapped up in romantic relationships, and how the year of dating herself helped her find, and keep, her own ground.
- Loneliness is real, and it’s survivable. Being intentionally single doesn’t mean you won’t miss romantic love. It means you learn you can miss it and still be okay.
- You don’t have to wait until rock bottom. Dating yourself isn’t just for the heartbroken. Whether you’re in a relationship or not, carving out time to be with yourself makes you a better partner, friend, and human.
- Compassion is curiosity. When asked what compassion means to her, Abby’s answer was beautifully simple: instead of painting someone with a one-dimensional brush, get curious about what they might be carrying.
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