Define Normal

The Single Friend Chronicles: Dating in Your Late 20s with Amanda Oswald


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In this episode, Shelbi Jones is virtually joined by her college roommate and friend of a decade, Amanda Oswald, as they reflect on their experience as single friends in their group. They dive into the cultural differences between Midwest and East Coast dating, the challenges of navigating “serious relationships” when you’re still single, and the death of situationships as they enter their late 20s.


They also share personal dating advice, offering insights on everything from dealing with FOMO (fear of missing out) to what it means when friends settle into relationships. This episode is a candid look at friendship, love, and the evolving nature of dating as you age.


Topics discussed in this episode:

  • Midwest vs. East Coast dating: What’s different about romance in other regions?
  • Navigating relationships as a single friend: What does it feel like when your friends get serious?
  • The death of situationships in your late 20s: Why things shift and what it means for your dating life
  • Giving dating advice to each other: Lessons, challenges, and reflections from two single friends


Referenced in this episode:

  • Girls Gotta Eat Podcast: Amanda references an episode with author Jon Birger about where all the decent men are. You can listen here.
  • TikTok on celebrating men doing the bare minimum: Check out the TikTok here.

Connect with Amanda Oswald:

Follow Amanda on Instagram at @aoswald11.


Hosted on Acast. See acast.com/privacy for more information.

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Define NormalBy Shelbi Jones

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