Jackson has built an intentional and fulfilling life for himself. He has a supportive family and many friends, and a career he really enjoys. There is an overall sense of contentment with the way things are, but after a series of unexpected challenges he wonders if he's missing out by not having a romantic partner to share in his highs and lows.

This week on the show Mauricio and Jackson explore what it would look like to start intentionally dating for the first time.

The Real Question is a Not Sorry Production

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