Jordana, Sami, and Aleen start the fifth episode of the season exactly where we left off last time, with the story of Sami’s little-known *gasp* first engagement. She tells us all the details about how she ended up in Israel during her mid-twenties, almost fell into an orthodox lifestyle, and met the guy who would eventually become her ex-fiancé. They talk about how easy it is to feel lost in your twenties, and why we make decisions out of confusion and uncertainty. Aleen and Jordana share some of their biggest mistakes from the past, and talk about why it’s hard to feel regret about experiences that shape you. Then a listener writes in to ask if she’ll ever find closure after a devastating breakup from her first love. Do we idealize our past relationships too much? Finally, they close the show with a game of Red Flag or Deal Breaker: Mistakes Edition, featuring some dating faux pas and a conversation about how you would react if your partner said someone else’s name during sex.

Learn more about your ad choices. Visit megaphone.fm/adchoices