Lil Xan’s romantic life has unfolded in recent years with a ferocity that is remarkably reminiscent of the unadulterated feelings expressed in his songs. Even though Diego Leanos, better known by his stage name Lil Xan, has persevered through criticism from the industry, addiction treatment, and creative reinvention, his high-profile relationships still dominate discussions on social media and in celebrity feeds.
His relationship with Annie Smith is one of the most talked-about periods in his romantic timeline. At first, their relationship seemed incredibly sincere, full of promises of love and plans for a future together. Fans enthusiastically embraced Lil Xan’s announcement on Instagram in February 2019 that he and Annie were expecting a child, hoping that fatherhood would provide a sense of stability to his frequently chaotic lifestyle.
Lil Xan (Diego Leanos) – Personal Profile and Relationship Timeline
| Full Name | Nicholas Diego Leanos |
|---|---|
| Stage Name | Lil Xan (also known as Diego) |
| Date of Birth | September 6, 1996 |
| Birthplace | Redlands, California, USA |
| Profession | Rapper, Singer, Songwriter |
| Music Career Start | 2015 |
| Famous Tracks | “Betrayed”, “Live or Die”, “Miss Me” |
| Known Girlfriends | Noah Cyrus, Annie Smith, Tana Mongeau |
| Label | 3rd Eye Recordings |
The public disarray that ensued, however, brought to light how brittle digital trust can be. Fans discovered shortly after the announcement that Annie’s ultrasound photos remarkably matched pictures that could be found via a Google search. These findings raised doubts about the veracity of her pregnancy claims and sparked a larger internet investigation. Lil Xan acknowledged in an open podcast interview that he was “50/50” on whether the pregnancy had truly happened. Although he acknowledged that he had not personally observed the entire process, he made reference to seeing positive tests and a growing belly, which caused uncertainty and unease among his fan base.
When trust, which was already brittle in a relationship this young and fast-paced, started to crumble under public scrutiny, the situation became even more complicated. Annie persisted in claiming that she had miscarried, posting heartfelt messages to her fans. Their once-loving public messages vanished into silence as Xan’s skepticism increased. Although it wasn’t confirmed right away, Lil Xan described the relationship as “too difficult to sustain” and ultimately blamed it on emotional toxicity and unresolved tension.
Lil Xan was infamously associated with singer and actress Noah Cyrus prior to Annie. Despite its short duration, their relationship was very well-known. They worked together on the single “Live or Die” and made their red carpet debut at the MTV VMAs. However, viewers were drawn in by the drama surrounding their split. Somehow, a miscommunication about a Charlie Puth meme led to infidelity accusations, which subsequently turned into heartfelt confessions. Noah rejected the relationship as an error, but Xan would later claim that he accepted responsibility for their breakup.
He carried that theme of intense emotion into other brief relationships, such as his notably ambiguous relationship with influencer and YouTuber Tana Mongeau. Although they were never formally verified, their public and online interactions implied a degree of intimacy that strengthened the rapper’s reputation for pursuing high-risk, high-reward emotional relationships.
The way Lil Xan’s relationships appear to follow a similar pattern—rapid attachment, public declarations, and eventual dissolution under scrutiny—is especially intriguing. It closely resembles the effects of the digital age on dating, where intimacy is frequently sped up by visibility and complicated by audience reaction. These partnerships, particularly those involving celebrities like Annie Smith and Noah Cyrus, were not merely romantic tales; rather, they were public spectacles influenced by the responses of followers and rumors.
But what makes Lil Xan unique is his candor. In addition to publicly discussing his experience with addiction and heartbreak, he has freely admitted his past transgressions and emotional immaturity. Reframing his image as someone who is actively learning in real time, rather than as a cautionary tale, has been made possible by his decision to remain vocal about these experiences.
Lil Xan’s transparency is especially novel in the entertainment sector, where image is carefully controlled. Through his social media accounts, podcasts, and interviews, he shares his vulnerability, which provides a unique form of intimacy. It’s the kind of candor that, although dangerous, can also be very potent, particularly for fans who prefer emotional authenticity to flawless perfection.
Since his album Diego was released a year ago, there has been a discernible change in tone. While processing the emotional devastation of previous decisions and implying a desire for personal development, the music leans toward introspection. Once the epitome of reckless abandon, the rapper now seems to be actively rebuilding. That journey is demonstrated by his recent sobriety milestones, which he publicly celebrated with his followers. He has been able to maintain his relevance while removing himself from the spectacle that once enthralled him by staying rooted in his story.
The history of Lil Xan’s relationships also provides a more comprehensive understanding of the difficulties that young artists encounter when navigating celebrity. The combination of personal and public life can be especially daunting for up-and-coming creatives, particularly those who make their debut on social media. Relationships change while being closely observed. Errors are magnified and replayed. Furthermore, it’s easy to confuse performance with authenticity. Despite being dramatic, Diego’s experiences in this setting are very relatable to his generation.