1. Kim Kardashian and Kanye West
Relationship Status: Dating since spring 2013; engaged since October 2013.
Quick History: The reality star, 33, met the "Yeezus" rapper, 36, in 2004 and the duo became fast friends. After years of keeping their relationship strictly platonic and two failed marriages, Kim finally gave in to Kanye's advances. The pair have jetted all over the world and welcomed their first child together, North West, on June 15, 2013.
Matchmaker's Verdict: Kanye has always been obsessed with Kim. She's his queen. Even though he's in love with himself and he thinks everything is about him, his heart softens when he is around Kim. Kim is the love of his life. That relationship works because she needs so much attention and he feeds it to her. She feels very stable and secure. They're going to last. They're going to get married.
2. Charlize Theron and Sean Penn
Relationship Status: Dating since January 2014.
Quick History: The Oscar winners have been pals for years, but romance rumors first emerged in 2010 after Theron, 38, split with her longtime partner, Stuart Townsend. While Charlize and Sean claimed they were "just friends," the duo sparked rumors again in October 2013 after they were spotted flirting at Seth MacFarlane's Halloween party. They rang in the New Year together in Hawaii and finally cemented their relationship status at Penn's Help for Haiti benefit. The pair have been inseparable ever since and the former bad boy, 53, has even been spotted doting on the South African stunner's adorable 2-year-old son Jackson.
Matchmaker's Verdict: I like them together. Sean Penn is known for being a bad boy. Charlize is not only beautiful and angelic; she's extremely smart. She is no dummy. She can put Sean Penn in his place. That relationship will work as long as Sean Penn stays in his lane — meaning he can't get angry or aggressive or act like a spoiled brat. Otherwise she'll open up the door and say [don't] let the door hit your a-- on the way out. He respects her. He looks up to her. He worships her. That relationship is going to last.
3. Jennifer Aniston and Justin Theroux
Relationship Status: Dating since May 2011; engaged since August 2012.
Quick History: The former "Friends" star became more than just pals with her "Wanderlust" co-star and was spotted cozying up to Theroux in May 2011. After one year of dating — and regularly dressing in nearly identical ensembles — the hunky screenwriter popped the question to Aniston during his birthday weekend. "Justin Theroux had an amazing birthday on Friday, receiving an extraordinary gift when his girlfriend, Jennifer Aniston, accepted his proposal of marriage," Theroux's rep said at the time. After a long engagement, there is still no wedding date on the books.
Matchmaker's Verdict: Jennifer Aniston is a scorned woman. When Jennifer was with Brad Pitt, all he said was, "Baby, all I want to do is have a baby." She said, "My career, my career." She couldn't do it. Jennifer with this new guy is saying I am committed to you. They're really working hard. There are some bumps in the road, but at the end of the day I think that she's finding her way.
4. Mila Kunis and Ashton Kutcher
Relationship Status: Dating since April 2012.
Quick History: The cute couple met while starring on "That '70s Show." At the time, a 15-year-old Mila confessed that her first on-screen kiss with Kutcher, then 20, had been her first kiss in real life, too. Clearly, it must have been a powerful lip lock. The pair reunited in 2012, just five months after Kutcher split from his wife, Demi Moore. Kunis, 30, and Kutcher, 36, prefer to keep their relationship under the radar, but earlier this year they attended two family weddings together.
Matchmaker's Verdict: Absolutely they're going to last. Now only time will tell. When he was dating Demi, there was the age difference … he wanted to have a baby. He's still a child. With him and Mila, they're going to get married and they're going to have a baby.
5. Kaley Cuoco and Ryan Sweeting
Relationship Status: Started dating in August 2013; wed on December 31, 2013.
Quick History: "The Big Bang Theory" actress, 27, was spotted spending time with the pro tennis player, 26, over the summer and they made their red carpet debut as a couple at a Golden Globes pre-party in September 2013. Things progressed quickly and the pair became engaged that same month. Cuoco gushed to "Entertainment Tonight" about their quickie courtship saying, "From day one, I just knew immediately and it's been magic. We have all the same family friends. We grew up with the same people, we just never met." The duo said "I do" in a fairytale wedding over New Year's Eve 2013 and have been going strong ever since.
Matchmaker's Verdict: All I have to say is, after that information that relationship is not going to last. I'll tell you why: When you are in your 20s, you have to take your time. It takes three to six months to get to know somebody. You don't jump into something. You have to work your way up. Anything that happens fast ends fast. That is my rule.