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My roommate Reid is back! After living together for three years in our East Village apartment, we're moving out.

This is his second time on the podcast and it’s the perfect time because we're both going through some major life changes right now. Reid is moving out to live with his girlfriend and I'm going to live on my own for the first time. Reid also just finished a pretty long job search - 50+ interviews across 10+ companies over several months. After dealing with lots of rejection, he landed a great new role and learned a lot along the way. He talks about working with an interview coach, how he stopped sounding rehearsed in interviews, and his approach to salary negotiation. If you're considering a job change, Reid's experience offers some useful perspective.

We talk about his six-year relationship which has been long-distance the entire time. Reid explains what's worked for them and his advice for long-distance relationships.

Since we've been roommates for three years, I wanted Reid's thoughts on what makes roommate situations work well. We talk through the practical stuff that matters more than you'd think like cleaning habits and talking about friends coming over. We also talk about why most guys are terrible at keeping in touch with their friends.

Then Reid takes on my "Dear Guyset" segment, addressing topics like dating uncertainty, relationship disagreements, asking for a raise, and managing workplace conflicts.

What We Cover:

  • Surviving a brutal job search and coming out stronger
  • Long-distance relationship tips that actually work
  • Roommate advice for guys in their twenties
  • Moving in with your girlfriend for the first time
  • Why we're all terrible at texting our friends back
  • Workplace advice and career transitions

If you're navigating any major life transitions in your twenties, this one's for you.

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See you guys next Tuesday.

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110 episodes