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Engagement
![Disaster Averted: Leonardo DiCaprio is Not, and This Can't Be Stressed Enough, NOT Engaged](https://chumley.barstoolsports.com/union/s3/2024/03/27/3340615d.jpeg?crop=4%3A3%2Csmart&width=3840&format=pjpg&auto=webp&quality=85%2C75)
![Regular Casanova Pulls Off The Riskiest Marriage Proposal Of All-Time And Knocks It Out Of The Park](https://chumley.barstoolsports.com/union/2024/01/29/gunpoint-proposal.0ebb0bb3.png?crop=0.85%2C0.75%2Cx0.00%2Cy0.00%2Csafe&width=3840&format=pjpg&auto=webp&quality=85%2C75)
![Substituting Your Local Olive Garden For Italy In Your Engagement Photos is The Ultimate Fake It Till You Make It](https://chumley.barstoolsports.com/union/getty/2023/06/12/GettyImages-1241413355.eb10c2e9.jpeg?crop=4%3A3%2Csmart&width=3840&format=pjpg&auto=webp&quality=85%2C75)
![Zendaya Responded To Rumors That She Is Engaged To Tom Holland Based On Her Instagram Story](https://chumley.barstoolsports.com/union/getty/2023/07/12/GettyImages-1358259452.cfa4377b.webp?crop=4%3A3%2Csmart&width=3840&format=pjpg&auto=webp&quality=85%2C75)
![](/images/stool.png)
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The Dog WalkProposing At Someone Else's Wedding (Free Swim)
![Proposing On A Flight Is Absolutely Insane And Even Worse When The Airline Makes Fun Of You For It](https://chumley.barstoolsports.com/union/getty/2023/07/14/GettyImages-168725875.46a9d852.jpeg?crop=4%3A3%2Csmart&width=3840&format=pjpg&auto=webp&quality=85%2C75)
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![Olivia Culpo Saying She Was 'Annoyed' With Christian McCaffrey Is Exactly Why Society Needs To Change The Engagement Ring Process](https://chumley.barstoolsports.com/union/getty/2023/05/25/GettyImages-1464829340.d3b85d2d.jpeg?crop=4%3A3%2Csmart&width=3840&format=pjpg&auto=webp&quality=85%2C75)
![Best Video Ever: A Guy Hopped Into The Field To Propose And Got Absolutely Truck Sticked By Security](https://chumley.barstoolsports.com/union/s3/2023/03/31/704220f6.jpeg?crop=4%3A3%2Csmart&width=3840&format=pjpg&auto=webp&quality=85%2C75)
![Preposterous: Drake Got Himself A Necklace With 42 Engagement Rings To Represent The 42 Times He Thought Of Proposing To Someone](https://chumley.barstoolsports.com/union/getty/2021/03/04/GettyImages-1153778013.5c14993c.jpeg?crop=4%3A3%2Csmart&width=3840&format=pjpg&auto=webp&quality=85%2C75)
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Chicks In The OfficeIf You're Doing This At Your Wedding You Need To Re-Evaluate Your Life
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![Adele Showed Up To The Brit Awards With A Big Honking Ring That Sure Looks A Lot Like An Engagement Ring](https://chumley.barstoolsports.com/union/2022/02/09/79571016aba3.jpeg?crop=4%3A3%2Csmart&width=3840&format=pjpg&auto=webp&quality=85%2C75)
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![An Absolute King Announced An NFL Draft Pick On Stage With His Girlfriend Then Proposed To Her By Quoting Deadpool With A Ring Pop In His Hand](https://chumley.barstoolsports.com/union/2021/05/02/Untitled-7.4a3196ee.png?crop=4%3A3%2Csmart&width=3840&format=pjpg&auto=webp&quality=85%2C75)
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![Tommy's Thursday Thoughts: Vol. 91 - Extraordinary Thoughts](https://chumley.barstoolsports.com/union/2020/10/29/Screen-Shot-2020-10-29-at-11.40.29-AM.4d36d28d.png?crop=0.99%2C0.94%2Cx0.01%2Cy0.00%2Csafe&width=3840&format=pjpg&auto=webp&quality=85%2C75)
Tommy's Thursday ThoughtsTommy's Thursday Thoughts: Vol. 91 - Extraordinary Thoughts
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Tommy's Thursday ThoughtsTommy's Thursday Thoughts: Vol. 79 - The First Texts