April Masini Plays Celebrity MatchMaker: Who Should Date Whom in 2007?

Clooney — Reese Witherspoon! She’s classy, she’s cute, she’s already got her Oscar, she probably doesn’t want any more kids — although who wouldn’t with George?? And she can hold her own with him at any Hwood party they give or go to. Can you spell power couple?

Or, if Reese doesn’t float his boat, Hilary Swank, would be just young enough to make him feel like he’s robbing the cradle, always an ego booster for men over 30, and equal enough because she’s got her Oscar, and she’s hung out with Clint Eastwood and Morgan Freeman — who should be playing poker with George and Brad Pitt in an Annie Liebowitz photo, anyway — or at least doing an Ocean’s 29 with George.

And last but not least, can anyone in Hollywood spell Pam? Pamela Anderson has done far more with far less than most people have or can do. She’s turned into a very decent mom with a solid job and some bad choices in men — doesn’t that make her everywoman U.S.A.? I would love to see George with Pam. He’d be her knight in shining armor, and she might even be the next Cher with his spotlight. He’s got such a classy veneer, that it might be a great place for trash and treasure to meet — as a couple that is George and Pam.

K-Fed — K-Fed should meet up with his right hand. Or his employment counselor. Maybe Paris Hilton needs a project.

Eminem - Shana Moakler! Hands down. She’s his type physically, and she’s a step up from his former Mrs. MnM, Kim M. She’s also a nice person who’s capricious enough to keep him interested, and mature enough to be a step-mother to his daughter. Someone get them a reservation at Hyde, pronto!!

Vince Vaughn - Vince needs to sow his oats. The poor guy did a good deed by dating Jen after she was dumped and crumpled by Brangelina, and didn’t know how to say no, after things got cozy. He should never have proposed to her — because it was pretty obvious he was stuck in a good deed he should never have committed in the first place. So now, Vince needs to get his ya yas out before he can focus on what’s right for him. My recommendation is stay away from college girls with blogs and have some fun with Courtney Love (she’ll make you forget your troubles and give you some interest-Q) until you’re ready for a real relationship. Then, speed dial Salma Hayak or Penelope Cruz (BFF so just pick one). You could use a real woman like these gals, who don’t really need a man (Jen did — and does), but want to love life to it’s fullest.

Jennifer Aniston - Jen. We love you. Buy my book — Think & Date Like A Man! You need my help because you are so like so many of my readers who don’t see what’s right for them, and are just looking to fill a void — that you think you have. No dating for a year. Just lots of pottery and knitting and Pilates. After which….you emerge, a hot babe on the scene — think graduation from Betty Ford — and snag that John Cusack who’s been in hiding for so long. We WANT to see him with someone who’s an equally nice girl compared to his sister, Joan. He comes from a stable family with nice people. Make babies — or a adopt twins (that’ll give Brangelina a jealousy pang) — or triplets! I can see the cover of People Magazine now. Best Personal Comeback! Then move to Chicago to be near the Cusack clan. Pay attention to Demi Moore’s personal history. You could learn a few tricks.

Britney - Get Rosie O’Donnell to hook you up in the lesbian circle. We know you like girls, and you don’t have to be ashamed. In fact, it would be the perfect slap in the face to K-Fed (and we ALL want to see that happen — he used you, honey!) if you rebounded with a hot chick. Please step away from the curb where the trailer trash with bucks live (Paris) — and find someone who works just as hard as you do. If Anne Heche wasn’t currently heterosexual, she might be an interesting choice, and if Ellen weren’t hooked up with Portia, she’d co-host the greatest dance parties ever with you.

However, your pretty normal upbringing (with respect to mom and dad and work ethics and home towns) might lead you back to your variation on Norman Rockwell. Britney loves pretty boys who can dance, so how about one out of two — Snoop Dog??

We WANT to see this match. You’re both from the same side of the tracks. You both love making a good living and living well. You both love music. You both have kids and exes. Please, please, please — we want to see this one!!

Paul McCartney — Cheryl Crowe – can Eric Clapton puh-lease make the introduction? All she wants to do is have some fun — and she’s got her own money. She’d be fine with a pre-nup. She’s been burned. He’s been burned. She’s musical. He’s musical. Remember Edie Brickell and Paul Simon? No! That’s right, because like Paul McCartney and Cheryl Crowe — they are a perfect match who are making a perfect life instead of ugly headlines. Paul! Give your ex your millions and make sweet love with Cheryl. Think of the London dinner parties! Madonna, Gwenyth, Ringo and Eric — I want an invite!

Reese Witherspoon - George Clooney, George Clooney, George Clooney. He will make you forget the terrible alimony settlement you’re going to have to make to Ryan since you didn’t have a pre-nup. He’s refined enough that your parents will respect him in a way they never did Ryan.

Pam Anderson - Sascha Baron Cohen. He was the reason behind the break up of your marriage. He’s hot. He’s uninhibited. He’s talented. He’s going to be rich. He’s nuts. He’ll get just as naked as you will. He will get into a ring with your exes and not think twice about taking them on to protect you. He’ll even share your pole in the bedroom. You may have to convert, but Judaism is hot right now — think Madonna — the wedding will be sick!

Kid Rock - Paris Hilton. Hands down. Kid, you are so cute, and unstable. The Hiltons will lend you some stability. Plus this Stavros thing is going nowhere fast. Paris needs a little rough and tumble in her life — and someone to kick Brandon Davis to the curb. Ugh.

Chris Robinson - Nicole Richie. He likes women with small breasts and Hollywood families — Nicole is perfect for him. Besides — we want to see Goldie Hawn as his ex-mother in law and Lionel Richie as his next father-in-law. Kate Hudson is the kind of person who will be friends with her ex and his wife — she’d be a great BFF for Nicole. It’s a win win all around. Thanksgiving with the Hawn clan and the Richie clan will be better than any Scientology party any day of the week.

Whitney Houston - Jeremy Piven. Someone needs to take this handsome, talented actor down a few notches, and Whitney knows how to bust a few. She is the only woman he will ever respect. She’s gorgeous, she’s age appropriate, she’s lived, she knows Hollywood AND the music scene. She has one child — not sixteen — and he can handle being a step-father to a daughter. Plus, she’s used to hot heads, and he’s less likely to use or get arrested than her ex. A step up for her. She’ll take him to the next level.