Watch: Usher Says He Regrets Not Dating Aaliyah, Reveals Monica Was His ‘First Celebrity Kiss’

Published: Tuesday 1st Mar 2022 by Rashad

Usher is no stranger to making headlines for his confessions, but his latest couple of reveals have had R&B fans jaw-dropped.

The 43-year-old, hot on the promo trail in support of his second Las Vegas residency (as we reported here), dropped by E! News Daily Pop to drop details on the forthcoming venture ahead of its July 15 kick off.

When the conversation turned to his personal life, the dad-of-four – currently in a relationship musical director Jenn Goicoecachea – surprised resident interviewer Francesca Amiker when he revealed the missed romantic opportunities of his past with some pretty big named music stars.

Watch inside:

When asked what celebrity he wishes he would’ve dated back in his younger years, Usher said, “somebody that I was really good friends with that I wish I would have taken more serious.”

“She was a really, really close friend of mine for a small amount of time,” he continued before revealing the person in question was late R&B songstress Aaliyah. “And then we just kind of disconnected.”

She wasn’t the only chart-topping diva in Ush’s orbit at the time, however.  His ‘Slow Jam’ co-star, GRAMMY winner Monica, was also stealing kisses from the ‘Good Kisser’ singer as he name-dropped her as his first celebrity kiss.

Click “Play” above to watch the fun-filled interview and hear more of his confessions.

[main photo sources: Getty Images/AP Photos]

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  1. eric March 1, 2022

    Interesting. No wonder he wanted to record a tribute album to Aaliyah. I can’t find that story in the news archives anymore, but I remember it.

  2. Truth March 2, 2022

    Yasss Usher and Mo. I’m glad he didn’t get to break Aaliyahs heart. Usher was a little heartthrob

  3. True Tea March 2, 2022

    Clearly Usher is threatened by attractive successful women.

    -Chilli
    -Monica
    -Aaliyah

    He caught so much heat when he introduced his baby mama. He may fear the idea of possibly being overshadowed.

    I can kinda understand since there are times when Beyoncé overshadowed Jay-Z, especially when performing together. Same w/ Whitney & Bobby. Cardi & Offset.

    • Sgt March 2, 2022

      None of these women would have overshadowed him lmfao what? Aaliyah didn’t really pop off until she died and Monica’s music was more famous than she was. Chilli was irrelevant outside of TLC. She was fading at the time of their relationship. Left Eye had died by then and TLCs last album flopped without her. Usher was huge back then. One of the biggest artists at the time. His fame eclipsed all of theirs combined.

      • eric March 2, 2022

        Aaliyah had Academy Award and Golden Globe Award nominations at age 19, and two top 5 singles with her first album. Usher saw his first hits around the same time, ’97 and ’98. Both artists were hugely popular.

      • True Tea March 2, 2022

        You’re correct in terms of being the bigger R&B artist but that doesn’t necessarily mean Aaliyah, Monica OR Chilli would have been LESS Interesting than him since they all have qualities that could have taken some attention away from the star.

        Allegedly this was the issue Monica & Brandy had when they collaborated. And the same was also said about Brandy & Countess Vaughn from Moesha.

      • True Tea March 2, 2022

        @eric

        Exactly! Aaliyah was beautiful but also alluring w/ out doing OR saying too much. She had such a LOW-KEY vibe, that was polarizing for most Female POP stars. She challenged the perception of an Entertainer. Aaliyah was bigger than her music.

  4. Divab March 2, 2022

    Yeah I believe this and also heard he tried really hard to get with Beyoncé

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