Jeff Hiller’s Big Breakup Speech

Love Letters

The Boston Globe

Love Tips, Breakups, Dating, Relationship Tips, Love, Dating And Relationships, Love Advice, Advice, Dating Tips, Marriage Advice, Breakup Advice, Relationship Advice, The Boston Globe, Boston, Society & Culture, Love Letters, Meredith Goldstein, Dating Advice, Letters, Relationships, Boston Globe

4.6 • 1.3K Ratings

🗓️ 9 September 2025

⏱️ 32 minutes

🔗️ Recording | iTunes | RSS

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Summary

Jeff Hiller, a 2025 Emmy nominee for “Somebody Somewhere” – is a very funny man. A dramatic man. A theater man. A man with many feelings. What do thoughtful performers do when they get dumped? They make a screen-worthy speech. A proclamation. Like Julia Roberts saying “Choose me!” in “My Best Friend’s Wedding.” Or Conrad saying “I still love you” on “The Summer I Turned Pretty.” In this new episode, Jeff shares a hilarious and intimate story about a breakup in his 20s – and the short speech that followed. He and Meredith discuss the pros and cons of making big proclamations, especially if you’re talking to someone who doesn’t even reciprocate. Expect laughter, lessons, and DRAMA. Love Letters is also an advice column. Send your question about your relationships (romance, friendship, family, etc.) to [email protected]. You can also tell Meredith about a speech you made – and how it was received! Sign up for Meredith’s newsletter – with behind-the-scenes pics, giveaways, and other extras – at boston.com/meredith . Episode art courtesy of AP. Learn more about your ad choices. Visit megaphone.fm/adchoices

Transcript

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0:00.0	When I was about 16, I was in love with a boy named Brad.
0:08.0	If you went to my high school in Maryland and are wondering, Meredith, do you mean that Brad?
0:14.0	The answer is yes, I do mean that Brad.
0:17.0	And yes, I've googled him lately.
0:19.0	And yes, I know he lives in Connecticut.
0:22.2	Anyway, Brad was sweet and smart with orangey blonde hair.
0:27.8	He made rhubarb pie.
0:29.9	He played the trumpet.
0:31.4	I loved Brad.
0:33.3	Deeply, spiritually.
0:35.4	I'm serious about this.
0:36.6	I think he was actually my first real love. And Brad,
0:40.4	he liked me a lot. As a platonic friend, I sort of knew this crush I'd been harboring on Brad
0:47.0	was one-sided, but on a random summer evening, I did something dramatic. I thought, I'm going to tell him. I was leaving his house
0:57.7	after a night of hanging out with friends. These friends hopped into her car and were about to drive me
1:02.9	home. But I turned back around. I went right back into Brad's house. He was still in his living room
1:09.3	alone, cleaning up after the get-together.
1:11.9	And I said, from what I remember, something like, Brad, I think I'm in love with you.
1:20.4	I remember Brad just standing there, frozen. He would have been about 18. And he was like,
1:28.1	okay. Then he was like, okay.
1:31.2	Then he just stared at me with a face that said,
1:33.9	can we please end this conversation, please?
	...

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