When people say, “personality is all that matters,” this might be what they’re referring to. Hollywood is filled to the brim with stunningly beautiful women, and plenty of undeniably handsome men as well. But, many of these sexy females haven’t gone after their physically attractive equal, but rather have landed themselves with men who have been far below their league, looks-wise.
Have you ever looked at a photo of J-Lo and Marc Anthony from when they were together and thought, “why…just why?” We might not be able to ever crack the case as to why some of the most gorgeous and sought-after celebrities, such as J-Lo, end up with some of the most average-looking individuals. We can only assume that behind the scenes they are compatible in ways we might not be able to recognize. Perhaps these men help keep the women grounded, or always have them laughing, or are of the kindest people in the world.
Whatever the exact rationale may be, major kudos to the men that have landed these women. While some of the relationships might have not worked out completely, at least they are able to say they spent some time dating someone far more beautiful than them (and, sometimes, far more famous as well).
Here are 13 female celebrities who have put personality before looks, and dated well below their league, on an attractiveness level.
13. Kate Moss – Pete Doherty
Kate Moss – one of the most beautiful models of our time – has become notorious for dating men who are not so beautiful. For one, her time spent dating musician Pete Doherty provided endless paparazzi photos of the completely mismatched pair, and caused many people to question what was going through her mind. Pete often looked like he could barely stand (or even talk), let alone handle dating a top model.
She also dated guitarist Jamie Hince for quite some time – another iffy choice. Other highly debatable men Kate has dated include Jack Osbourne, Russell Brand (allegedly) and Rhys Ifans, just to name a few. While she is undoubtedly smart about her career, it seems she is a bit clueless when it comes to finding men of her own beauty caliber.
12. Clare Grant – Seth Green
Clare Grant, who is known for her acting, singing and modeling, is undeniably attractive. So when she first stepped out with the tiny redhead actor, Seth Green, people weren’t sure what to make of the pairing. Although Clare is both taller and far easier on the eyes, the couple married. The duo has worked on two films together throughout their relationship: Robot Chicken and Warren the Ape. It’s possible working together has kept the spark alive, because today the couple has been married for five years. Despite their ability to keep the relationship going, each time they appear on a red carpet it’s obvious that Seth is “winning.”
11. Mary-Kate Olsen – Olivier Sarkozy
The mere thought of Mary-Kate Olsen and the much-older Olivier Sarkozy makes many cringe. They are notoriously mismatched, both in age and looks. They first went public with their relationship in 2010, leaving the public scratching their heads. Not only is Mary-Kate far tinier and younger, she is also very obviously far more beautiful.
However, they announced that they were engaged in 2014, showing they could care less what others thought about them and their evident physical differences. Many have said they equate the way Mary-Kate and Olivier look together as a daughter and father, which is especially creepy and gives an even more awkward feel to the pair.
10. Kristen Bell – Dax Shepard
Fans were stumped when the gorgeous actress Kristen Bell began dating the awkward-looking Punk’d star, Dax Shepard, back in 2007. What’s more, the odd couple has actually lasted. They were engaged two years after dating, but decided to wait to get married until same-sex marriage was legal in California.
And, they did just that – holding off until October 2013 to tie the knot, just a few months after sex-same marriage became legal in their state. Now, the two have a daughter, Lincoln, and seem to be happy as ever. While their looks might make them seem completely different, both seem to be similar at heart, and share interests, such as eating and living a vegan lifestyle.
9. Christina Aguilera – Jordan Bratman
Christina Aguilera has been a sex symbol since she first came on the music scene with “Genie in a Bottle,” and sexed it up even more with her follow-ups like “Dirrty.” On her rise to fame, she has dated some hot celebrities of the moment, including Enrique Iglesias and (supposedly) Carson Daly. But in her older years, she’s taken a major downhill turn in the quality of men she’s ended up with.
She was married to music marketing executive, Jordan Bratman, who is anything but traditionally handsome. They were together for many years before separating, but Christina didn’t move on up to someone more attractive. She is currently dating the often-scruffy looking guitarist Matt Rutler, who is not much of a looker, either. While they’re currently engaged, rumors have recently swirled that they are arguing over a pre-nup, so only time will tell what will happen.
8. Katy Perry – Russell Brand
Katy Perry has definitely dated some attractive men, but she also has made some highly questionable choices as well. For instance, Katy married actor/comedian Russell Brand in 2010, and despite their differing looks and unlikely success as a couple, they stuck together for a few years before divorcing in 2014. Apparently, Russell, who was previously a known drug addict, announced he wanted a divorce via text message to Katy, which seems shocking considering how far out of his league Katy was to begin with. After Russell, she also made a memorable MTV Video Music Awards appearance with the out-right dreadful Riff Raff. Luckily, it didn’t seem as if the two were officially dating (though it was never truly determined), and rather just hoping to show off their matching denim outfits, ala Britney Spears and Justin Timberlake.
7. Christina Hendricks – Geoffrey Arend
The stunning actress Christina Hendricks has one of the dorkiest looking husbands in Hollywood – though the two do appear to be madly in love. Her husband, actor Geoffrey Arend, is one lucky man. In fact, Christina actually was the one who pursued him. They have openly talked about the fact that she tracked down his number, made the first move and even said “I love you” first.
She was so aggressive from the get-go that she even told him on their first date that she hoped to one day start a family with him. They married in 2009 and are still going strong today. As if her husband wasn’t attracted to her enough, Christina has said that to extend the honeymoon period of their relationship, she tries to regularly get dressed up for him and refuses to wear sweatpants.
6. Salma Hayek – François-Henri Pinault
While Salma Hayek’s husband is a billionaire, he is nothing compared to her when it comes to beauty. She and François-Henri Pinault met in 2006 and had their daughter soon after. When they broke up for a while in 2008, the public wasn’t sure what would happen, but ultimately they got back together and married. Even though she is physically far out of his league, it didn’t stop him from cheating.
Years after it happened, the world learned François-Henri had fathered a child with a Canadian model while he was dating Salma. Making it even worse – Salma was pregnant with their child at the same time the model was pregnant. Talk about absolutely horrible timing. For a reason none of us will ever understand, Salma stayed with her husband, and the two are still making it work today.
5. Pamela Anderson – Kid Rock
Pamela Anderson has, for a long time, been a staple in the world of great looks, but she has really gone off the deep end with some of the men she chose to call her partner. For one, she was famously married to the “American Bad Ass” Kid Rock, who is slinky and whose appearance is anything but traditionally desirable. Though the two didn’t last long, it didn’t stop them from having many PDA moments together while things were good, leaving many on-lookers wanting to cover their eyes.
But, Kid Rock wasn’t the only questionable man Pamela chose. She’s also dated other men far less attractive than she, including names like Fred Durst, Arsenio Hall, Criss Angel (yikes) and was even rumored to have dated David Spade.
4. Heidi Klum – Seal
One of the world’s most stunning models-turned-household names, Heidi Klum, could have nearly anyone she chooses to date in the world, but somehow ended up married to singer Seal. It was very obvious that Seal was really, really lucking out by snagging Heidi.
However, for whatever her reason may have been, Heidi seemed smitten. While the pairing definitely was shocking when it first happened, over time people grew on the thought of them together, figuring she must have highly enjoyed his knack for singing, or possibly his personality. They ultimately married and had four children together. But, after seven years of marriage the two split.
3. J-Lo – Marc Anthony
Jennifer Lopez, too, has dated some very attractive men in her time including her high-profile relationship with heartthrob Ben Affleck, but when she landed on the eerie and frail Marc Anthony, she seemed to have found her match. He is far from attractive, though the two were making it work, and ultimately got married and had two children together. Despite the media picking on him – dubbing him “Skeletor” – the couple appeared to be dodging any shots taken at their relationship.
However, as it is in Hollywood, the two ended up divorcing. But, J-Lo ended up moving on to another man far below her beauty level: backup dancer Casper Smart. He is far less appealing to look at, and is 18 years her junior. But regardless of their on-and-off status, they now seem to be going strong.
2. Christina Milian – Lil’ Wayne
Christina Milian is currently dating one of the tiniest and scrappy-looking rappers out there – Lil Wayne. The two allegedly started dating last year following Christina’s split from her former fiancé Jas Prince. They’ve kept their relationship mostly mum, but it hasn’t stopped the paparazzi from catching them out together. And, their differences in looks are striking, to say the least. As if anything could be stranger than how low she’s stooped in terms of looks by choosing Lil Wayne as her man, the two have an extremely odd family connection. Christina has a child with her ex boyfriend, The Dream. Lil Wayne’s ex-girlfriend, Nivea, also has two children with The Dream, as well as a child with Lil Wayne. This makes their families highly and creepily intertwined.
1. Isla Fisher – Sacha Baron Cohen
The beautiful redhead actress, Isla Fisher, has been with one of Hollywood’s oddest and homily characters, Sacha Baron Cohen (aka Borat), for a very long time. The two dated for many years before marrying in 2010. Not only are his hairy looks and wild antics concerning enough, he is also known to find himself involved in a variety of lawsuits thanks to his films, which are often deemed offensive.
Isla has admitted in the press before that, while things are smooth with their relationship, Sacha often embarrasses her with his bizarre actions (remember when he spilled ashes all over Ryan Seacrest on an Oscars Red Carpet). But, aside from the troubles with his behavior, Sacha seems to make Isla happy, and the couple now has two children.
- Ad Free Browsing
- Over 10,000 Videos!
- All in 1 Access
- Join For Free!