4.6 • 4.6K Ratings
🗓️ 2 January 2026
⏱️ 11 minutes
🧾️ Download transcript
Chelsea and Catherine get an update from a caller who married his longtime love and assess a friend-zoning situation.
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Executive Producer Catherine Law
Edited & Engineered by Brad Dickert
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| 0:00.0 | This is an I-Heart podcast. Guaranteed human. Hello, Gatherine. Oh, hi, Chelsea. How are you? I'm feeling very deep-throated today. Yes. I kind of am, too. I don't know. Is it the weather? |
| 0:15.6 | Maybe. Maybe. I spoke to a little bit of a joint, so... Well, I have a really fun update. |
| 0:22.4 | So I'm not sure if remember Witt from our John Lovett episode. |
| 0:26.4 | He was getting serious with his girlfriend and wanted to propose, but wasn't sure about telling her family that he's trans. |
| 0:33.5 | Oh, yes, I remember. |
| 0:34.4 | Yes. |
| 0:35.0 | We loved Witt, and I think we did update that they got engaged and that was all very happy. |
| 0:40.3 | So I got a very special email this week. |
| 0:44.1 | This email is from Aaron. |
| 0:47.9 | So Aaron says, hi, Chelsea. |
| 0:50.7 | I couldn't help but think of you and the experience you shared with my son, Witt, when he appeared on the Dear Chelsea podcast last year. This is Witt's mom. I've been a long-time |
| 0:59.0 | listener of Chelsea's podcasts and have enjoyed her episodes on Netflix and YouTube for years. |
| 1:04.2 | Whit and I even binge-watched some of them together when I visited him in Montreal. So I was thrilled |
| 1:09.1 | when Catherine arranged for Witt to be on the show and have the chance to ask Chelsea and John questions about his dating relationship. Shortly after the episode aired, Witt proposed to Ann. She said yes. The heart of the episode was about whether Witt should tell Anne's parents that he's trans before they got engaged. Chelsea and John suggested it really shouldn't matter either way. As it turns out, Anne's parents are incredible people. They were extremely understanding and expressed that they were honored, Witt and shared that part of their story with them. They emphasized that it didn't change how they felt. It simply didn't matter to them in the best way. Witt's experience on Dear Chelsea gave him confidence and validation beyond what I could have imagined. The respect and dignity Chelsea and John brought to the conversation through their openness, |
| 1:47.8 | inclusion, and compassion was truly refreshing. |
| 1:50.7 | As Witt's mom, I want to say how much I appreciate all of you. |
| 1:54.0 | Today, I'm flying to Montreal for Witten Anne's wedding, and I felt it was the perfect time |
| 1:58.1 | to reach out and express my gratitude for the kindness you showed, |
| 2:08.8 | warmly Aaron. Oh my God. I know. Wow. I know. It's just like so lovely. Keeping families together. |
| 2:14.7 | That's what we're doing. Keeping families. I mean, to get a thank you letter from someone's mother, |
| 2:18.0 | it's like the best gift ever. I know. It's so delightful. |
| 2:22.9 | So thank you so much for writing in Aaron. And by the way, what a beautiful model and blueprint for anyone's who is dealing with anyone, you know, the way that this couple reacted to finding |
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