The judge revealed his liking for Alesha Dixon's assistant Francesca Neill to his co-stars, before saying that he has yet to speak to her.
"We have the new, cutest make-up artist. But I just can't talk to her, I'm kind of tongue-tied," Cowell said on ITV2 spin-off show Britain's Got More Talent.
When asked by host Stephen Mulhern if he wanted to put in a good word for him, the music mogul said: "No, that would make it awkward."
David Walliams then suggested that Neill already has a boyfriend, before Mulhern teased: "I hear he's a cage fighter".
A friend of Cowell told The Sun: "Simon thinks Francesca is beautiful - and, of course, he has a soft spot for make-up artists."
Neill - who used to date Craig David - has also supplied make-up for the likes of Matt Cardle, Nadine Coyle and contestants on Strictly Come Dancing.
Cowell separated from fiancée Mezhgan Hussainy earlier this year, after he reportedly claimed she was "needy".
> Simon Cowell armed intruder: Leanne Zaloumis remanded in custody