What Men Actually Think About Before They Propose ft. Mark Manson

LOVERS by Shan

Lemonada Media

Relationships, Society & Culture, Sexuality, Health & Fitness

5.0 • 5.7K Ratings

🗓️ 18 March 2026

⏱️ 74 minutes

🔗️ Recording | iTunes | RSS

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Summary

Have you taken my MasterClass yet? New subscribers get access to my class and hundreds of others starting at $10 per month. Right now, our listeners get an additional 15% off any MasterClass annual membership at http://masterclass.com/lovers ________________________ In this episode of Lovers, I’m joined by Mark Manson, the bestselling author of The Subtle Art of Not Giving a F*ck, Everything Is F*cked: A Book About Hope, and Models: Attract Women Through Honesty, to talk about what men actually think about before they propose, and why waiting doesn’t mean what you think it means.Mark shares the story of how he “agonized” over proposing to his now wife of ten years. Despite being deeply in love, he struggled with doubt, timing, and the pressure to feel completely certain. The turning point came during a conversation with his stepmother, who told him she had been married for over thirty years and still couldn’t say with absolute certainty that she “knew” he was the one. That advice freed him from the illusion that certainty is required before commitment.We also unpack my own proposal story with Jared, including the untold truth about the pressure I put on him to propose and what was actually happening behind the scenes. The story I shared online isn’t the full story, and in this episode, we fill in the missing pieces.Lauren Morrison, my sister and the author of Be in the Room, joins as guest host. As a longtime fan of Mark Manson, she helps us dig into the myth of the two-year rule, the idea that if a man hasn’t proposed by a certain timeline, you must not be “the one,” and the false belief that real love comes with instant certainty.This conversation challenges the cultural narrative that a proposal delay reflects doubt about your worth. Instead, it reveals how doubt is often part of the process, not a sign that something is wrong.If you’ve ever wondered what’s taking so long, this episode is for you. Get MasterClass Today For real, what are you waiting for? My class on MasterClass is one of the best things I’ve ever done and I’m sure every other instructor would agree! Go to http://masterclass.com/lovers Get an additional 15% off any MasterClass annual membership Follow Mark Manson → Instagram: https://www.instagram.com/markmanson/→ Listen to Mark’s podcast: https://podcasts.apple.com/us/podcast/solved-with-mark-manson/id1247526593→ Sign up for Purpose and experience Love Maps: https://purpose.app/ Follow Lauren Morrison → Instagram: https://www.instagram.com/coachlaurenmorrison/→ Get Lauren’s new book https://www.amazon.com/Be-Room-Shrinking-Leading-Purpose/dp/B0FM4HGYSP→ Sign up for a free coaching consultation with Lauren https://www.beintheroomcoaching.com/work-with-laurenWant more Lover?Receive the weekly Love Letter → http://loversbyshan.com/newsletterJoin the Lovers Community → https://www.loversbyshan.com/communityExplore quizzes and worksheets → http://loversbyshan.com/quizzes See omnystudio.com/listener for privacy information. Learn more about your ad choices. Visit megaphone.fm/adchoices

Transcript

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0:00.0	It's supposed to be fantastical and you described it to Lauren and I as agonizing. Yes. Within two years, you want to be engaged or marry. The man decide that you're his wife. He's not going to waste any time. Because he's going to hunt until he feel like stopping. When you're going to marry that girl? You know, my career was hitting its stride. It felt like every woman I was meeting was just incredible. And then I met my wife.
0:21.1	And it's just like everything felt easy.
0:23.7	It felt right.
0:24.7	But it was just terrifying.
0:26.2	I'm like, what if I'm wrong?
0:28.2	This abundance of optionality is secretly undermining a lot of people's ability to actually build or foster intimacy with the people that they're dating.
0:36.5	I think it's backfiring in a lot of significant ways. My stepmom, she was like, what are you waiting for it? I was like, well, I don't know. Like, how do I know if I'm going to be happy with her in 20 years, if I want to spend the rest of my life with her? And she was like, Mark Manson. She's right. She's right. So the next day I went, I went ring shopping.
0:54.8	How does your wife feel knowing that...
0:58.0	In 2014, I met my husband through Afeon Crockett. A year later, we had our first hang, then bang.
1:04.5	In 2016, we made it official and moved in together. In 2017, I heard him tell his best friend
1:10.0	that he knew for certain he was
1:12.0	going to spend his entire life with me. At the end of that year, we opened up an S-corp and started
1:16.1	approaching everything as life partners who loved the hell out of each other. And then, I waited.
1:23.1	And I waited and I waited. Until eventually, I had to start asking the question I was hoping he was going to ask me.
1:29.3	Bro, do you want to get married?
1:32.3	Because if you do...
1:34.3	This woman right here, this beautiful girl, is in a relationship.
1:38.3	She's found a guy of her dream.
1:40.3	Now, until this dude decides she's the chick of his dream, we don't have a match,
1:46.9	folks, because he going to hunt until he feel like stopping. I hate to tell y'all that. Oh, my God.
1:52.3	What are you going to do? Back then, I was praying for content that validated the experience of
1:57.2	somebody in a healthy, loving partnership where both parties said that they wanted marriage,
	...

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