5 times Kimberly Guilfoyle and Donald Trump Jr’s PDA made us cringe: From grandma hug to tepid kiss

A look at Kimberly Guilfoyle and Donald Trump Jr's cringey PDA moments, ranging from awkward kisses to unromantic interactions
PUBLISHED SEP 9, 2024
Donald Trump Jr and Kimberly Guilfoyle has displayed some awkward PDA moments since getting into a romantic relationship (Anna Moneymaker/Getty Images)
Donald Trump Jr and Kimberly Guilfoyle has displayed some awkward PDA moments since getting into a romantic relationship (Anna Moneymaker/Getty Images)

Kimberly Guilfoyle and Donald Trump Jr have displayed quite a few PDA-filled moments over the years. Their lip kisses at times turned weird when the couple appeared together for events to boost and support former president Donald Trump. Guilfoyle got engaged to Trump Jr in November 2020, but nearly four years later, there are no signs of an impending wedding. However, they appeared together at the 2024 Republican National Convention in Milwaukee. The absence of a wedding date gave rise to split rumours, which Guilfoyle tried hard to dismiss. Their often cold and weird interactions hardly helped to quash the speculations. Here are five cringey PDA moments between Trump Jr and Guilfoyle.

1. The head-collision kiss

(CNN screenshot)
Donald Trump Jr appeared struggling to breathe as Kimberly Guilfoyle kissed him during a Turning Point USA event in 2018 (CNN screenshot)

During a Turning Point USA event in October 2018, Trump Jr and Guilfoyle were at the beginning stage of their romantic relationship. This perhaps explains their awkward kissing moment. The relatively new couple kissed on stage, but it looked less like a brush of lips and more of a head collision. Guilfoyle held the face of Trump Jr, who apparently struggled to take a breath as he balanced his hands on the back of her waist.

2. The chop-chop kiss

(C-SPAN screenshot)
Donald Trump Jr gave a tepid kiss to Kimberly Guilfoyle at the Sportsmen for Trump panel discussion in 2020 (C-SPAN screenshot)

Trump Jr does not always prefer to turn his PDA with Guilfoyle passionate. There are times when it lasted only for fleeting seconds. At the Sportsmen for Trump panel discussion in San Antonio, Texas, in October 2020, the former first son couldn't get over Guilfoyle's attempt for an affectionate kiss as she pulled Trump Jr, holding his shoulder. The moment lasted only seconds as Trump Jr signalled to end the PDA with a touch on her elbow. The kiss thus ended on a tepid note. At the time, the couple was two years into making their dating public.

3. The CPAC canoodling

DALTON, GEORGIA - JANUARY 04: Donald Trump Jr., son of U.S. President Donald Trump, kisses his partner Kimberly Guilfoyle during a Republican National Committee Victory Rally at Dalton Regional Airport January 4, 2021 in Dalton, Georgia. President Trump campaigned for the two incumbents, Sen. David Perdue (R-GA) and Sen. Kelly Loeffler (R-GA), for tomorrow’s runoff elections in Georgia. (Photo by Alex Wong/Getty Images)
Donald Trump Jr and Kimberly Guilfoyle's kiss at the 2021 Conservative Political Action Conference  (Alex Wong/Getty Images)

The 2021 Conservative Political Action Conference in Orlando, Florida, turned out to be another stage that witnessed a weird PDA moment between Trump Jr and Guilfoyle. Standing near the microphone stand, the former Fox News host appeared to suck the face of her fiance as she held tightly onto his shoulders. The then-52-year-old's kiss indicated the passion they shared as they moved hand in hand to promote former president Trump.

4. Social kissing 

(@kimberlyguilfoyle/Instagram)
Kimberly Guilfoyle gave a cheek kiss to Donald Trump Jr at a July fundraiser event in Alabama (@kimberlyguilfoyle/Instagram)

At certain moments, Trump Jr and Guilfoyle completely avoid their lips. In July 2024, the TV personality shared a picture of her social kissing the ex-first son. As per her Instagram caption, the moment was captured during a fundraising event for the GOP presidential nominee in Alabama. Social kissing or cheek kissing is a form of greeting and is entirely unromantic. Trump Jr and Guilfoyle's cheek kisses have often sparked speculations about the status of their relationship.

5. The grandma hug

(@kimberlyguilfoyle/Instagram)
Kimberly Guilfoyle's hug to Donald Trump Jr at the RNC in July looked more like a grandmother's display of affection (@kimberlyguilfoyle/Instagram)

Guilfoyle shared her excitement after delivering a speech at the Republican National Convention held in Milwaukee, Wisconsin, in July with a hug to Trump Jr. However, their interaction looked miles away from a PDA between a romantic couple. In a GIF shared on Guilfoyle's Instagram, she enveloped her fiance like a grandmother. Trump Jr patting her back also looked like a child receiving a hug from his grandmother rather than his future wife.

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