You know the dating pool is getting shallow when you’re facing the prospect of greeting your significant other during a conjugal visit.
Take a look at these 11 celebs who dated criminals and judge for yourself if they were just being loyal partners or seriously caught in the middle of the ultimate struggle relationships.
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Photo: Essence/YouTube screen capture
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Lil Kim
After she did a year in the bing for lying under oath, everyone was pretty much convinced Lil Kim had earned her hood pass. The game got deeper when it was discovered one of her exes was Damion “World” Hardy Brooklyn’s Cash Money Brothers. For some quick background, just know that Hardy feuded with Mike Tyson over Daryl “Hommo” Baum—the man believed to have emptied six shots into 50 Cent.
photo: LK WENN
Anne Hathaway
It was all good just a week ago until federal agents slapped the cuffs on Anne Hathaway’s boyfriend, Raffaello Follieri on charges of cheating investors, money laundering and exaggerating his ties to the Vatican for personal gain.
Phaedra Parks
Nothing kills a relationship faster than an eight-year prison bid. Such was the case when Real Housewives of Atlanta cast member Apollo Nida decided to bumrush his soon-to-be ex-wife instead of reporting to prison on charges of bank fraud and identity theft.
Mama June
If you’re wondering what happened to Here Comes Honey Boo Boo, the show was axed after Mama June rekindled her love with convicted pedophile Mark McDaniel. There’s something about these TLC shows and people hitting kids with the forbidden touch.
photo: WENN
Karrueche Tran
These days, Chris Brown doesn’t have a felony assault on his record for beating Rihanna down in 2009. But Breezy was definitely on papers throughout the duration of his relationship with Karrueche Tran. Say what you will about her, but she’s pretty much ride or die as long as you don’t knock up another chick behind her back.
Anna Duggar
Much like Mama June, Anna Duggar is down with a dude who likes to touch on kids. In June, an archived police report furnished by USA Today revealed Josh Duggar fondled a few underage females.
photo: WENN
Tameka “Tiny” Cottle
Based on T.I.’s rhymes, he was a repeat felon pretty much the whole time he was with Tiny. Sure enough, he’d been on seven years probation from 1998 through 2005 for felony drug charges. But there’s also that 2007 incident when Tip got caught with a small arsenal before the BET Awards.
Papoose
Let it be known Papoose rides for his woman. The curator of The Nacirema Dream held it down for six years while Remy Ma served hard time for assault, weapons possession and attempted coercion in the 2008 shooting of Makeda Barnes-Joseph.
Safaree
While Nicki Minaj has upgraded to Meek Mill, her ex-boyfriend hasn’t been as fortunate. Safaree Samuels got put on blast when it was discovered that his new boo Zashia Santiago has a strike on her record. In 2013, Santiago plead guilty to felony possession of 15 or more unauthorized access devices after reportedly jacking a bunch of hospital IDs.
Dirk Nowitzki
Perennial NBA All Star Dirk Nowitzki probably wanted a do-over after copping a $250K ring for his fiancée and alleged baby mother Cristal Taylor in 2009. Taylor racked up six digits worth of debt and had two warrants out for her arrest when Nowitzki found out in the middle of a playoff run.
photo: KIKA/WENN.com
Charlize Theron
Sean Penn isn’t a criminal in the recent or traditional sense. The outspoken, philanthropic actor caught two charges for assaulting paparazzi members and was reportedly involved in a domestic dispute with his wife Madonna in the ‘80s.
