The 58-year-old music mogul - who has son Eric, four, with girlfriend Lauren Silverman - is keen for his fellow 'Britain's Got Talent' co-judge to go out with his former partner, who he has always stayed close friends with, but David isn't sure the 'So Macho' singer would be keen.
David - who has son Alfred, four, with ex-wife Lara Stone - said: ''Last time I saw Simon he was trying to fix me up with Sinitta, who's single now.
''Imagine if that happened? She'd have gone from Brad Pitt to Simon Cowell to me. That's a steep decline! What kind of woman would go out with us three?''
The 46-year-old comic loves making jokes at Simon's expense on 'Britain's Got Talent' but they don't always make the cut.
He admitted: ''I love the funny, naughty, off-the-cuff moments.
''There was one thing I said which didn't make it into the final cut of the show, when we had Mr. Gay UK auditioning.
''He did his act and then, when it was time for our comments, I said to Simon, 'And now over to Mr. Bi-Curious UK'.''
David can't help but become ''annoying'' when he is around Simon, fellow judges Alesha Dixon and Amanda Holden, and 'BGT' hosts Ant and Dec.
He told Heat magazine: ''It's like when you go home to see your mum and you automatically regress back to behaving like a child.
''That's how I am on 'BGT'. I immediately become the annoying person I always am on the show.
''The thing that always surprises me is just how excited everyone gets.
''I think because they get to see Simon, Alesha. Amanda, Ant and Dec, the audiences feel they're at a big event.
''So you get all the shouting and screaming, which doesn't normally happen when I'm on my own. It's like the circus has come to town.''
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