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Reading: Jimmy Kimmel Trolls Trump and Melania’s Anniversary, Mentions Their ‘Beautiful Prenuptial Agreement’
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Entertainment

Jimmy Kimmel Trolls Trump and Melania’s Anniversary, Mentions Their ‘Beautiful Prenuptial Agreement’

Published on: January 23, 2026 at 9:42 AM ET

Jimmy Kimmel hilariously roasts Trump and Melania on anniversary night.

Pramila Tripathi
Written By Pramila Tripathi
News Writer
Divya Verma
Edited By Divya Verma
Senior Editor
Jimmy Kimmel continues trolling Trump
Jimmy Kimmel continues trolling Trump (Image via X / @DisavowTrump20 l Wikimedia Commons)

Jimmy Kimmel has proved time and again that he is not one to stop trolling Trump. Therefore, it was expected that he would not miss the opportunity to make fun of Trump and Melania’s 21st anniversary.

The president and the first lady reportedly celebrated their anniversary with a private dinner after Trump returned from the World Economic Forum. However, as Kimmel pointed out, much like their private dinner, the couple has also been rather private about their affection for each other, as there has rarely been any public display suggesting they have a great relationship.

In his opening monologue, Kimmel decided to go straight to the point, saying, “It’s a big day for the Trump family — it’s Donald and Melania’s 21st wedding anniversary. Twenty-one years ago today, Melania said, ‘I do,’ and a beautiful prenuptial agreement was born.” The comedian mimicked Melania’s accent while delivering the “I do” line, which drew loud laughter from the audience.

 

 
 
 
 
 
View this post on Instagram
 
 
 
 
 
 
 
 
 
 
 

 

A post shared by Jimmy Kimmel Live (@jimmykimmellive)

Kimmel also noted that although the president was returning from Europe just in time for his anniversary dinner, he did not seem to have time to post something nice for his wife. However, as Kimmel pointed out, “but he did take time to post something sweet. He posted a random guy calling him the ‘greatest president in the world,’ period, three exclamation points, and that was it, sorry, Melania.”

Trump’s social media postings are well-known, and therefore, the fact that he chose not to post anything specific for his wife on their anniversary says a lot about the state of their marriage, which has already been subject to speculation about a possible separation.

Aside from the anniversary dig, Kimmel also addressed the large bruise Trump was spotted with on his left hand. It should be noted that the president has previously been seen with similar bruises, which fueled health-related concerns. However, Press Secretary Karoline Leavitt said that because the president is extremely busy and shakes hands frequently, he developed those bruises. While there was considerable skepticism surrounding the explanation, the administration stood by it.

Kimmel, however, chose to draw attention to the latest bruise and tied it to the president’s conjugal life. He joked, “Let me just say this, Donald Trump’s going to have to be careful doing court-ordered lovemaking tonight because ‘Teddy Bruisevelt’ may have left his makeup kit at home, because first of all, he’s two totally different colors. His hand’s like a marshmallow’s face or a Costco rotisserie chicken, or something.”

 

 

 
 
 
 
 
View this post on Instagram
 
 
 
 
 
 
 
 
 
 
 

 

A post shared by The White House (@whitehouse)

Kimmel then went ahead to shred Leavitt’s previous explanation of the bruise, as he added, “He’s got a nasty bruise on his left hand, which doesn’t exactly square up with the ‘he shakes a lot of hands’ explanation for the bruises, and he didn’t even try to spackle over it this time.”

The comedian further continued hilariously, “His Press Secretary Karoline Leavitt put out a statement, saying he banged his hand on the corner of a table during a signing ceremony, and then again, spanking himself with that Nobel Peace Prize.”

In his signature humorous style, Kimmel roasted the President along with his administration and his personal life. It now remains to be seen if Trump again comes up with a new rant and demands of Kimmel being fired after this episode.

TAGGED:Donald TrumpJimmy KimmelMelania Trump
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