Millionaire Matchmaker! 10 Rappers and Singers Who Should Have Hooked Up in 2011

The Rapper: J. Cole

The Singer: Rihanna

Why They Should've Hooked Up: If not Drake, then Cole! We heard aaaaaaall about the alleged sex tape that Penthouse supposedly had in their possession earlier this year. But, it never actually surfaced. That being said, Cole seems a little like Jay-Z's little brother these days (Kanye's all grown up!) and Rih-Rih seems a little like Beyonce's little sister. So, wouldn't Cole and Rih make a cute couple? We sure think so.

The Rapper: Royce Da 5'9"

The Singer: Rihanna

Why They Should've Hooked Up: "Hiiiiiii, Rihanna!" Okay, okay. No more suggestions for Rihanna. But, you didn't seriously think we were gonna forget about Royce shouting her out at the 2011 BET Hip-Hop Awards, did you? For that alone, we would've liked to hear a few relationship rumors fly about the two performers.

The Rapper: Diddy

The Singer: Jennifer Lopez

Why They Should've Hooked Up: Once J. Lo and Marc Anthony broke up, you just knew the "J. Lo is getting back together with Puffy!" stories were going to fly. And they did. And then, for whatever reason, they stopped. C'mon, Jenny. You were the only girl who could keep Diddy tamed. And, Diddy, J. Lo still looks as bad as she ever did (or, at least, better than Cameron Diaz!). Why not reunite for old times' sake?

The Rapper: Kanye West

The Singer: Lady Gaga

Why They Should've Hooked Up: For the completely bizarre red carpet entrances! We're pretty sure we wouldn't believe that these two were a couple even if we saw them making out right before our very eyes. But, then again, 'Ye has been photographed sucking face with some model chicks who don't look all that different than Gaga. If you want a power couple, this is it!

The Rapper: Romeo

The Singer: Jordin Sparks

Why They Should've Hooked Up: Yo, how come nobody out there is trying to scoop Miss Sparks? In case you haven't noticed, she's looking good these days! Romeo's also all grown up now, too, and seems to be a hit amongst the ladies. So we could see these two—who were rumored to be dating back in July—spending some QT together. Hey, somebody out there has to try and kick it with Jordin. She's too pretty to be single.

The Rapper: Rick Ross

The Singer: Ciara

Why They Should've Hooked Up: The ultimate payback for 50 Cent! Fif started his year by beefing with Ci-Ci on Twitter. Ross also has a penchant for dating 50's exes—he kicked it with actress Elise Neal for awhile. And, not for nothing, Ciara could certainly use the boost for her career that would come with dating the Boss. Quick: Someone arrange this before the ball drops on NYE!

The Rapper: Lil Wayne

The Singer: Kelly Rowland

Why They Should've Hooked Up: On Kelly's hit single, "Motivation," these two had great chemistry. So great, in fact, that we're a little surprised that they weren't shacking up prior to recording the track. What gives, guys? Did you just have a natural chemistry—or was there something more here? We're hoping for the latter.

The Rapper: Wale

The Singer: Solange

Why They Should've Hooked Up: Almost every successful song off Wale's Ambition album involves an R&B hook. It's clear dude needs some lovin' in his life! (no shots! Those weren't the only tracks we liked from the album, homie! Just pointing out the facts...) So, why not rekindle whatever he had with Solange a couple years back? They could both use the tabloid boost right about now. And they actually seem like they'd make for a pretty compatible couple.

The Rapper: Big Sean

The Singer: Nicki Minaj

Why They Should've Hooked Up: Did you see the "A$$ (Dance)" video?! No rapper has gotten that close to Nicki's rotund rump in, well...forever. She clearly felt comfortable dancing up on him. Sean also said he didn't have to pay Nicki for her verse. So, what did he give her in exchange for it? Hmmmmmmm....We'll let you decide.