What happens when Broadway’s favorite Shakespeare gets real about love, legacy, and the role that got away? In this episode of Had to Ask, Drew Gehling (@drewgehling), currently starring as Shakespeare in & Juliet on Broadway, opens up about what it’s like to be part of a show he calls “the joy factory,” lighting up the stage eight times a week.

We talk about the thrill of watching audiences fall in love with & Juliet, his deep love for the theatre community (including a sweet shoutout to Erich Bergen) and the kinds of characters he keeps coming back to — especially the ones who are a little messy, a little vulnerable, and always trying to figure it out.

Plus, Drew also shares the story of his very first date with Julia Mattison, which happened right downstairs from where we filmed, and reflects on watching her rise as the co-composer and lyricist of Broadway’s Death Becomes Her.

It’s candid, funny, and packed with heart — just like Drew himself.

Chapters:

• 10:08 - The role that got away.
• 14:08 - Gravitating towards characters who are trying to show everyone they have it together.
• 27:02 - Literally rubbing noses with Joey Fatone.
• 29:34 - Drew's first date with Julia and being her biggest fan.
• 36:58 - Comparison and seeing the same 5 people in the waiting room.
• 40:22 - What happens when your hobby becomes your job.
• 43:42 - What Drew would be doing if he wasn't a performer.

Follow Drew @drewgehling and Had to Ask @hadtoaskpod for more bold, unfiltered conversations — hosted by Melanie Sutrathada.

Co-produced and edited by Joseph Loper. Special thanks to The Chatwal in NYC for being the home of Had to Ask for season 1!

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