Celebrity Matchmaking with Chilli

Dating With Chilli"What Chilli Wants" in a ManEverybody knows it's difficult to find love these days and for Chilli it's a bit harder — given her famous checklist. We decided to compile her past loves and challenge her checklist by matching her with few hot men. Learn about her old flames and see her thoughts on possibly dating Lenny Kravitz, Floyd Mayweather, Laz Alonzo and more. Plus see which Hollywood beauty she picks for herself!You be the match maker. In your opinion who would be a good match for Chilli?Past Flame: Dallas AustinIn her 20's Chilli married super producer Dallas Austin. Austin was responsible for many of TLC's hits including "Creep" and "Unpretty." The two share a son, Tron. Years later, the marriage ended in divorce and it would be quite some time until Chilli's next love came about.Past Flame: UsherUsher and Chilli dated from 2001 to 2003. Their steamy romance fizzled when rumors of Usher's alleged infidelity hit the net and surfaced in his "Confessions" CD. In 2004 when The Bert Show of Atlanta's Q100 asked if Usher cheated on her she replied, "Usher did the ultimate no-no to me... I will never be with him again, and that is that."ESSENCE.com's Pick: Floyd MayweatherNow on to the next possible loves...Chilli: No he's not the man for me. Floyd and I are friends. We definitely having love for each other, genuine respect and care for each other. Our relationship to me is very special because we've never slept together. It's always refreshing to hang out with a someone that's truly your friend that's the opposite sex and you don't have to worry them trying to sleep with you. He's very respectful.ESSENCE.com's Pick: Lamman RuckerChilli: I think he's handsome. Not for me, but he's a nice good looking man.ESSENCE.com's Pick: Idris ElbaChilli: He's another one with that sex appeal! He's real sexy and when he talks he has that sexy British accent. It's funny because you don't expect him to talk like that.ESSENCE.com's Pick: Lance GrossChilli: I think he's cute. He has sex appeal about him.ESSENCE.com's Pick: Reggie BushChilli: I know a lot of females like Reggie, but he's not my type at all.ESSENCE.com's Pick: Lenny KravitzChilli: OMG! I love Lenny, and he's also like family. If he wasn't family — there's something about Lenny that's really fly to me. I like the bone structure in his face. And he doesn't age! He Looks exactly the same! He has good genes. He's real healthy too, always stays in shape. But that's my brother.ESSENCE.com's Pick: Trey SongzChilli: Not a match for me but I think Trey is kind of cute.ESSENCE.com's Pick: Jamie FoxxChilli: Oh God! He's like a brother to me. It feels weird to think of him in a romantic way. That's like family.ESSENCE.com's Pick: TankChilli: (Laughs hard) Not my type, but he does have nice abs.ESSENCE.com's Pick: Laz AlonzoChilli: Now we're talking! Laz has that pretty boy look that I like. I think he's really good looking and he's an amazing actor. He's one of the best I think. I know him but I don't know him that well. I think he's really, really good looking.ESSENCE.com's Pick: Gabriel AubreyChilli: Ohhhhhh! He's hot! But I would never mess with him. Halle Berry and I aren't girlfriends, but we've hung out before. I could never date anybody that she's dated. It would seem kind of strange, but he is beautiful!Chilli's Pick: Chris PineChilli: He's gorgeous! He is in shape, but I don't know what he's like at all. He's just gorgeous!

Everybody knows it's difficult to find love these days and for Chilli it's a bit harder — given her famous checklist. We decided to compile her past loves and challenge her checklist by matching her with few hot men. Learn about her old flames and see her thoughts on possibly dating Lenny Kravitz, Floyd Mayweather, Laz Alonzo and more. Plus see which Hollywood beauty she picks for herself!You be the match maker. In your opinion who would be a good match for Chilli?

In her 20's Chilli married super producer Dallas Austin. Austin was responsible for many of TLC's hits including "Creep" and "Unpretty." The two share a son, Tron. Years later, the marriage ended in divorce and it would be quite some time until Chilli's next love came about.

Usher and Chilli dated from 2001 to 2003. Their steamy romance fizzled when rumors of Usher's alleged infidelity hit the net and surfaced in his "Confessions" CD. In 2004 when The Bert Show of Atlanta's Q100 asked if Usher cheated on her she replied, "Usher did the ultimate no-no to me... I will never be with him again, and that is that."

Now on to the next possible loves...Chilli: No he's not the man for me. Floyd and I are friends. We definitely having love for each other, genuine respect and care for each other. Our relationship to me is very special because we've never slept together. It's always refreshing to hang out with a someone that's truly your friend that's the opposite sex and you don't have to worry them trying to sleep with you. He's very respectful.

Chilli: I think he's handsome. Not for me, but he's a nice good looking man.

Chilli: He's another one with that sex appeal! He's real sexy and when he talks he has that sexy British accent. It's funny because you don't expect him to talk like that.

Chilli: I think he's cute. He has sex appeal about him.

Chilli: I know a lot of females like Reggie, but he's not my type at all.

Chilli: OMG! I love Lenny, and he's also like family. If he wasn't family — there's something about Lenny that's really fly to me. I like the bone structure in his face. And he doesn't age! He Looks exactly the same! He has good genes. He's real healthy too, always stays in shape. But that's my brother.

Chilli: Not a match for me but I think Trey is kind of cute.

Chilli: Oh God! He's like a brother to me. It feels weird to think of him in a romantic way. That's like family.

Chilli: (Laughs hard) Not my type, but he does have nice abs.

Chilli: Now we're talking! Laz has that pretty boy look that I like. I think he's really good looking and he's an amazing actor. He's one of the best I think. I know him but I don't know him that well. I think he's really, really good looking.

Chilli: Ohhhhhh! He's hot! But I would never mess with him. Halle Berry and I aren't girlfriends, but we've hung out before. I could never date anybody that she's dated. It would seem kind of strange, but he is beautiful!

Chilli: He's gorgeous! He is in shape, but I don't know what he's like at all. He's just gorgeous!

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