If Anita weren't boo'd up, she might wonder if there's someone in her life she already knows who is a good romantic match for her. But is it healthy to look to the past for a chance at future happiness? With help from the podcast Dating While Gray, we examine the pros and cons of "boomerang love."

- Jeannie Thompson talks about her own boomerang heartbreak that led her to leading online discussion forums on reconnecting with former loves.

- Grace shares what happened when she reconnected with a childhood crush after her long marriage had gone stale.

- Mary and Del, who split after the flame of desire went out in their 20-year marriage, answer the question: Can living separate lives reignite a spark?

Read the transcript | More Dating While Gray