Written by Staff Writers on
 July 19, 2025

Insights emerge into Aubrey O'Day, Donald Trump Jr.'s past relationship

Aubrey O'Day has shared introspective details about her past romantic involvement with Donald Trump Jr., a relationship that she says had both uplifting and damaging effects on her self-worth, as the Daily Mail reports.

Their connection, which was marked by mutual admiration and passion, ultimately met its end due to Trump Jr.'s infidelity, which played a role in his subsequent divorce from Vanessa Trump.

In a recent conversation with US Weekly, O'Day opened up about the nuances of her relationship with Trump Jr., which began in late 2011 and ended in the spring of 2012. At the time, Trump Jr. was married to Vanessa Trump. O'Day painted a picture of a deep emotional connection, saying that Trump Jr. made her feel beautiful and deeply admired her intellect, offering feelings of validation she cherished.

O'Day levels critique of Trump Jr.

Despite the positive aspects of their relationship, the affair came to an end when Vanessa Trump uncovered the infidelity. She discovered email exchanges between her then-husband and O'Day, which eventually led her to file for divorce in 2018. In light of this new information, many traced back the cracks in the marriage to the period of the affair.

O'Day doesn't shy away from expressing how the relationship affected her. In her words, she loved the person Trump Jr. was on the verge of becoming, before his quest for power altered that path. This insight gives a glimpse into the dissonance between the image of the man she loved and his actual actions that ultimately led to their breakup.

Adding more depth to her story, O'Day shared her reflections on social media. Using Instagram Stories, she addressed responses to her revelations about the relationship. She vowed to speak her truths candidly, emphasizing her commitment to honesty rather than sanitizing her story to maintain illusions.

Comparisons abound

O'Day's reflections on her relationship with Trump Jr. also prompted comparisons to other relationships in her past. She notably pointed to her time with Pauly D from Jersey Shore, with whom she had a publicized romance from 2016 to 2017. This comparison highlighted how different relationships served as learning experiences for her.

According to O'Day, her relationship with Pauly D left her feeling the lowest she had ever felt, contrasting sharply with the upliftment she experienced from Trump Jr. Despite the turmoil in her affair with Trump Jr., O'Day remains candid about the positive aspects of their bond, implying that it offered her a deeper sense of self-acceptance compared to her relationship with Pauly D.

Pauly D himself has acknowledged the nature of their relationship, expressing relief that it ended when it did. He emphasized that their breakup was a bullet dodged and reflected on how he found out about O'Day's past affair alongside the rest of the world.

Efforts to set record straight

Donald Trump Jr. has not made public comments about the affair, leaving O'Day's side of the story to take the forefront. Her revelations offer a unique perspective into a pivotal period in Trump Jr.'s personal history, elaborating on the elements that contributed to the dissolution of his marriage.

Currently, O'Day is featured on the E! series Botched Presents: Plastic Surgery Rewind, in which she continues to engage with her fan base. She also uses social platforms to address the perceptions people have about her, often challenging assumptions head-on.

One area where she wishes to correct misunderstandings is her relationship with makeup, stating she is just like any other woman in her approach. She frequently emphasizes how her artistic expressions, often heavily visual, intersect with her personal life, striving for authenticity beneath the makeup.

Legacy, personal growth emphasized

Moreover, the affair and its aftermath have not hindered Vanessa Trump from pursuing happiness. She has recently been romantically linked to Tiger Woods, navigating her path post-divorce. This new chapter in her life further contrasts the divergence in personal journeys for all those involved.

O'Day's openness about her past relationship with Trump Jr. underscores a narrative of self-exploration and personal evolution. While the affair might have ended years ago, its echoes continue to affect the lives of the individuals involved in varied and significant ways.

Ultimately, this chapter in O'Day's life represents more than a simple recount of the past. It serves as a testament to her growth, as she chooses to share her journey with self-love and authenticity as her guide.

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