1. OJ Simpson
OJ’s been locked up for a while now, so the smallest act of kindness would probably go a long way. Ask him about his day and he’ll be all yours, but be careful if you’re not looking for something serious—he’s supposed to get out in a couple years, and has a history of overreacting to romantic rejection.
2. Diane Keaton
Here’s a curious case–she dated Woody Allen, Al Pacino, and Warren Beatty at various points in her life, so you’d think she wouldn’t necessarily need a lot of attention to feel loved, but she wears outlandish outfits designed to draw the maximum amount of attention and remind everyone how vivacious and idiosyncratic she is. I’m betting she’d come on hot and heavy in the beginning, but after a couple weeks you’d refer to her as your girlfriend and she’d balk, like “I thought we were just having fun without labels” and you’d be like, “Oh, that’s cool, too” and then she’d cry for six hours that she’s never been with anyone that really understood her.
3. Chris Cooper
The smoldering Adaptation star seems like the type who’s slow to establish trust but has absolutely no boundaries with the people he feels close to, so make sure you’re very clear about what you’re comfortable with before letting those cold reptilian eyes lure you into the bedroom.
4. Scarlett Johansson
She was in The Avengers, you’ve been reading the comic for years. She did an album of Tom Waits covers, you were just listening to Rain Dogs in the car this morning. She’s said that her favorite place on Earth is Disneyworld; you’ve always talked about going, but don’t know anyone who wants to make the trip. Relationships have been built on less. Jesus, look at your parents. The only thing they have in common is their species and a fondness for the salad bar at Jason’s Deli, and they’ve been together thirty-six years.
5. Donald Trump
Behind all the bluster, the Trumpster strikes me as nothing but an old fashioned romantic. He’d sweep you away to Ibiza on his private plane, shower you with gifts, and maintain unbroken eye contact the entire time you were making love. If you can put up with the constant flow of super right wing, ill-conceived political garbage that he spews, you’ll end up with an office tower in downtown Miami named after you in no time flat.
6. Jennifer Aniston
Aniston’s failure to find a soulmate has been major tabloid fodder for years. Seems like she just can’t find anyone she can really connect with who’s ready to start a family but not threatened by her work coming first. Does that sound all that different from the fights you and Steph were having towards the end? When in one breath she’d tell you she wasn’t ready to start a family, and in the next get on your case about finishing your degree and getting a stable gig so she wouldn’t have to work once you started having kids? What the hell did she want from you? No hard feelings, she’s got to live her own life—but imagine how jealous it would make her to see paparazzi pics of you and Aniston smooching on an exotic beach. Let her see that and then look up at the fucking trailer she’s sharing with that dirtbag Dennis, see if he seems “like he really has his shit together” then. Sure, you miss her. You’ll probably die missing her. No, don’t fucking talk like that. She left. You have so much love to give, save it for someone worthy, like Jennifer Aniston.
7. Kim Jong-un
The thing about being a dictator elevated to godlike status is that it makes it tough to know when people are really being straight with you. Kim would find your candor super refreshing, and he seems like the kind of guy who’d be willing to let you mold him as you saw fit once he saw that you really cared. I mean, don’t get me wrong here, you probably won’t be able to get him to shut down the slave labor camps, but I bet he’d lose fifty pounds and grow his hair out if you asked.
8. Rush Limbaugh
Rush seems like one of those dudes who are constantly on the prowl for a girlfriend but who won’t ever settle down. He’d be good for a memorable fling, but after a month he’d ask you for a ride to the airport and then act like he was doing you a favor by letting you drop him off. You’d probably lose a dangerous amount of weight dating him, too. Look at that picture, it looks like he’s trying to inhale his date’s entree from across the table while she’s looking in the other direction. I don’t want to call Rush fat but I heard he special orders his belts from a company that normally manufactures fire hoses. Dude spends so much money at Burger King they bestowed his ass a dukedom. Had the shower head in his upstairs bathroom replaced with an insulin pump. All right, all right. Yeah, you could date Rush.
9. Johnny Galecki
Between starring in Roseanne and The Big Bang Theory, Galecki has had sex with hundreds of women—but he’s never, ever made love. Just once he’d like to know what it is to merge souls instead of just mashing guts. To sip sangria on a bed covered with rose petals instead of guzzling Coors in the back of a pedicab, to wake up in the arms of someone he truly loves instead of coming to strapped into a leather sex swing hanging from the ceiling and having to wait for one of the three unconscious Pizza Hut waitresses stacked in a pyramid beneath him to wake up and set him free.
Rihanna has terrible taste in men and an amazing propensity for granting unmerited second chances. If we weren’t made for each other, no couple was.