20+ Celebs Who Only Date People Out of Their League

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Celebrity relationships are a strange thing, especially when one of them is completely out of their partner’s league. The couples we feature might look happy together, but by just looking at them, we can tell that one of them has settled. Let’s see if you can tell which one settled and which is dating someone out of their league.

Mary-Kate Olsen and Olivier Sarkozy

The relationship between former child star Mary-Kate Olsen and French banker Olivier Sarkozy raised more than a few eyebrows when the couple made their relationship official in 2012. With an age gap of a whopping 17 years between the two, they somehow made it work and were married in 2015.

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Fast forward a few years, and it’s clear that the age gap was simply too much for the gorgeous Mary-Kate to bear. The unlikely couple announced their divorce in 2021, causing fans of the beautiful Olsen twin to sigh a breath of relief.

Taran Killam and Cobie Smulders

Who would’ve thought that How I Met Your Mother characters Robyn and Gary would end up together in real life? We certainly didn’t, but for Taran and Cobie, sharing an agent would result in a chance meeting that saw Cobie meet the man of her dreams.

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The couple was married in 2012. While they don’t have any children together, they’re still happily married. Critics and fans have often spoken of the actress settling for Killam, but in this day and age, do looks really matter that much?

Jesse Williams and Aryn Drake-Lee

Grey’s Anatomy heartthrob Jesse Williams shocked fans when he made a red carpet appearance with his long-time wife, shortly after his rise to fame. While many thought she married him for his fame and money, the truth is a much sweeter story.

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Aryn and Jesse met long before his fame. A teacher at the time, Jesse met real estate agent Aryn and fell head over heels in love. The couple married in 2012, but sadly parted ways in 2017. They share two children together.

Seth Green and Clare Grant

Seth Green and Clare Grant could be the poster couple for the saying “love is blind.” A full head shorter than his wife, Green met Grant in 2006 at the re-opening of their favorite comic book store, Golden Apple Comics. A love for comic books and fast food got this pair to start dating.

Facebook // Clare Grant

This cute couple was married in 2010 and is still together today. It just goes to show that even short men can find true happiness. We don’t want to even think about how different it’d be for the two had Grant not been photographing the opening of the store that fateful day back in 2006.

François Henri-Pinault and Salma Hayek

When Mexican actress Salma Hayek started dating French billionaire businessman François in 2006, many thought the relationship was doomed from the start. But, somehow, it just worked, and the couple welcomed a daughter together in 2009 before sealing the deal and tying the knot in 2009.

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While the media labeled Hayek as nothing more than a golddigger, fans were wondering why the beauty would settle for a man that’s nothing special to look at. The couple has, however, dismissed reports of her being with him for his money and are still happily married.

Pete Davidson and Kate Beckinsale

SNL star Pete Davidson hasn’t had much luck with relationships, which had fans of Kate Beckinsale wondering if the actress had hit her head when she first started dating Davidson in 2019. Despite their 20-year age gap, the couple seemed happy enough. But, as everyone expected, the relationship burned out soon after.

(Left) Flickr // Gerald Geronimo | (Right) Flickr // Greg2600

Davidson and Beckinsale called it quits after only four months together. Perhaps it was a relationship of convenience or a rebound, but the pair split amicably. We didn’t see Pete Davidson settling down back then, and we certainly don’t now, as he’s fresh out of a relationship with the gorgeous Kim Kardashian after only nine months together.

Roberto Cavalli and Lina Nilson

Not even a 40-year age difference could stand in the way of legendary designer and fashion mogul Roberto Cavalli finding love in the arms of Swedish woman Lina Nilson. Having met in 2013, the couple has been together for a decade and has no intentions of splitting any time soon.

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Cavalli is by no means bad to look at, but looking at these pictures of the happy couple together does make one wonder how he landed such a hottie. Is it a case of true love? Or does his money and business success have something to do with it?

Adam Brody and Leighton Meester

This addition to our list is a bit of a difficult one to work out. Both actors in the teen series industry, Brody and Meester, started dating in 2013. A wedding followed a year later, with the couple proclaiming their love for each other in front of friends and family.

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Still together today, the couple have two children and live a fairly private personal life away from the ever-prying eyes of the public and the pesky paparazzi. It’s good to see that Blair Waldorf finally found her happily ever after with Seth Cohen.

Orlando Bloom and Miranda Kerr

Following his new-found fame after his appearance in The Lord of The Rings trilogy, Orlando Bloom met and married model Miranda Kerr after three years of dating. The couple welcomed a son together shortly after but finalized their divorce in 2013.

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Thankfully, both have gone on to find true love again. Orlando is now engaged to pop star Katy Perry, with whom he has a child. Miranda is with her husband of five years, Evan Spiegel. The couple is said to have remained friends and amicably co-parent their son.

Hugh and Crystal Hefner

We all knew it’d happen sooner or later, and in Hugh Hefner’s case, it’d be much later that he’d fall in love with former Playboy Playmate Crystal. Despite a whopping 60-year age gap between the two, Hugh and Crystal were married in 2013.

Facebook // Crystal Hefner

Though the relationship was nothing short of bizarre, Crystal and Hugh were still happily married when he sadly passed away in 2017. While the couple didn’t welcome any children together, Crystal is a stepmom to Hugh’s four children, who love their stepmother dearly.

Michael Sheen and Sarah Silverman

Actor Michael Sheen thought he’d found his soulmate in comedian and actress Sarah Silverman. Having dated for four years, friends of the famous couple were waiting with bated breath for the wedding bells to sound. But as fate would have it, their relationship came to an end in 2017.

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Sheen has always been rather eccentric, and sources close to the star have shared that the breakup was caused by Michael’s many political associations and his drive to be an activist. Silverman didn’t share her beau’s dreams and called it quits.

Max Minghella and Elle Fanning

Writer and director Max Minghella struck gold when he met beautiful actress Elle Fanning on the set of the teen movie Spirit in 2018. Absolutely smitten with his new-found love, Minghella has proudly accompanied his lady-love to red carpet events, smiling boldly for the cameras.

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While he’s not unattractive, it’s Fanning that has fans guessing why she seemed to settle for a man that’s not in her league. But despite these horrible remarks, the couple is still happily together today and more in love than ever.

Jay-Z and Beyoncé

Jay-Z and Beyoncé is considered one of America’s most powerful couples. With a number of successful businesses behind their names, Beyoncé met Jay-Z in 2001. They dated for a good few years before making it official in 2008, collaborating on Beyoncé’s Crazy in Love album to celebrate their love.

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Jay-Z and Beyoncé became proud parents to Blue Ivy in 2012 and later welcomed twins Sir and Rumi in 2017. Still together all these years later, the couple is still collaborating on a few business ventures but focuses their time and effort on their most important venture yet – their family.

Pete Davidson and Kaia Gerber

Yes, you read that right. Pete Davidson is in another odd relationship, but this time it’s his relationship with model Kaia Gerber. His only relationship with a younger woman to date, Davidson and Gerber, dated for a few months from 2019 to 2020.

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It was Gerber, the daughter of supermodel Cindy Crawford, who ultimately called it quits as she realized that the age difference between them was too much and that he had more than a few issues that she wasn’t willing to deal with.

Evan Peters and Halsey

This is another relationship that has us puzzled, as we can’t figure out which one settled and which one was reaching out of their league. Nonetheless, Dahmer star Evan Peters dated the gorgeous Halsey for six months, eventually ending the relationship in mid-2020.

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While the couple insists that they ended things on friendly terms, sources close to them say that it was a really bad breakup that saw Halsey question how she could have ever dated the actor. Young love is tricky to navigate, but Halsey’s happy ending would come just a few short months later.

William H. Macy and Felicity Huffman

Shameless star William H. Macy has been married to the gorgeous Desperate Housewives star Felicity Huffman for over 26 years. Marrying in 1997, the couple has one of the longest relationships in Hollywood and are still as in love today as they were all those years ago.

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Macy and Huffman are parents to two beautiful daughters. Recently in the press for their involvement in a college admissions scandal, the couple live a relatively quiet life raising their children away from the public eye.

Orlando Bloom and Katy Perry

It’d take a number of failed relationships – including a marriage to model Miranda Kerr – for Orlando Bloom to find the love of his life in singer Katy Perry. Having met only a few months before their engagement, the couple welcomed a daughter in 2020.

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Bloom and Perry are yet to make their way down the aisle, but those in the know say that they can see a wedding in the very near future. While some say that Perry is far too good for Bloom, we know that looks aren’t always important to her. That’s already been seen in her marriage to comedian Russell Brand who asked for a divorce via a text message.

Hugh Jackman and Deborra Lee-Furness

Australian couple Hugh Jackman and Deborra Lee-Furness have been happily married for over 26 beautiful years and have two adopted children together. But, a 13-year age difference between the hunky actor and his wife has many wondering just how Deborra bagged herself such a catch.

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Despite being happily in love, there are always those who try and make a mountain out of a molehill, looking for scandal where there is none. And while it may be hard to accept, it’s clear that Jackman and his wife are more than happy together and have 26 beautiful years of marriage to prove it.

Pete Davidson and Margaret Qualley

In true Pete Davidson style, we bring you another failed relationship, this time with actress Margaret Qualley. The daughter of gorgeous actress Andie McDowell, Margaret met the young Pete Davidson in 2019. After a short two-month romance, which many referred to as a vacation fling, the couple called it quits.

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We can’t blame poor Margaret for this one, as she found the age difference between her and her beau too much to handle. Or perhaps it was his string of failed relationships with older women that ultimately drove her away? Whatever the case, we’re glad she saved herself from the heartbreak of being with serial dater Pete Davidson.

Max Handelman and Elizabeth Banks

Looking at pictures of beautiful actress Elizabeth Banks and her husband, Max Handelman, one can’t help but wonder what she sees in him. But, the truth is that Banks and Handelman were college sweethearts and tied the knot way before the actress became a household name with movies like Pitch Perfect on her resume.

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Having been together for 30 years and married for 20 of those, the couple seems to have a fairytale-like love story as they happily parent their two sons. While Max focuses on his company, Brownstone Productions, his wife is still acting and has been in a number of record-breaking movies since the start of her career.

Josh Henderson and Audrina Patridge

Much has been said about the relationship between actor Josh Henderson and The Hills star Audrina Patridge, but much of it isn’t entirely true. Spotted together in 2019, the rumor mill worked overtime as they shared the news of the two being in a happy relationship.

(Left) Facebook // Audrina Patridge | (Right) Facebook // Josh Henderson

This “relationship” was all but shut down by the pair, as they’ve both stated on numerous occasions that they share nothing more than a close friendship. Hmm, you keep telling yourselves that, Josh and Audrina. We all know that there’s something more between you two.

Sacha Baron Cohen and Isla Fisher

Ali G funnyman Sacha Baron Cohen met his love match when he was introduced to the stunning Isla Fisher at a party in 2002. After getting engaged after a six-year relationship, the couple made it official and tied the knot in 2010.

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Now, 13 years later, the couple is still happily married and keeps their personal life very private, not even sharing photographs of their two children. With many wondering how Cohen got so lucky in the first place, it’d seem that nothing can break these two up.

Michael Sheen and Rachel McAdams

It seems that Michael Sheen is nothing more than an older version of Pete Davidson. The Notebook star Rachel McAdams, who’s 10 years his junior, started dating Sheen in 2010.

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Meeting on the set of the movie Midnight in Paris, the couple would go on to date for two years before they ultimately split in 2012. McAdams has never been open about what caused the split, but those in the know say that it was because the actress and Sheen shared different visions for the future.

Howard Stern and Beth Ostrosky

How on earth did shock-jock Howard Stern land himself a wife as good-looking as Beth Ostrosky? Having met the model when she was a young woman, Stern popped the question after dating for seven years. The couple wed in 2010 and are still together today.

Facebook // Beth Stern

Though there’s a whopping 18-year age gap between the two, they seem happy enough as they’re pictured here smiling and happily married. It just goes to show that there’s someone special out there for everyone, and it might just take a long time to find the one who makes it all worth it.

Jesse Plemons and Kirsten Dunst

It’d seem that love really is blind when you look at the relationship between beautiful actress Kirsten Dunst and fellow actor Jesse Plemons. While she’s nothing short of a hottie, Plemons isn’t exactly easy on the eyes, and he somehow managed to convince Kirsten to become his wife.

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Dunst met her future husband on the set of the 2014 series Fargo and they officially started dating in 2016. Becoming engaged after only a year and welcoming two children a few years later, the couple officially sealed the deal when they were married in late 2022.

Jeff Richmond and Tina Fey

Composer Jeff Richmond and actress Tina Fey have come a long way since they first started dating. Tying the knot in 2001, Richmond supported his comedian wife’s dreams of becoming an actress years before she would become a household name.

Flickr // Nick Step

Now, having been together for more than two decades, the beautiful star and her husband share two children. While you might think she’s with him out of pity, it’s clear that Fey loves and adores her husband just as much now as she did when they first met.

Benji Madden and Cameron Diaz

Former Good Charlotte rocker Benji Madden struck gold when he met actress Cameron Diaz in 2014. The couple married after only a year of dating and welcomed a baby girl, who they named Raddix. Covered in tattoos, Madden is nothing like the men that Diaz used to date, leaving fans wondering how the two struck it off so easily.

Instagram // @benjaminmadden

Diaz and Madden live a very private but happy life together. Careful about what they do and don’t post on social media, the public is yet to get a glimpse of their daughter, who’s around two years old by now. No matter what anyone says, it’s clear that Madden makes Cameron happy.

Pete Davidson and Kim Kardashian

Good grief, Pete! Is there no end to the number of women you’ve dated? 2022 saw a new relationship blossom for Davidson as he started dating none other than Kim Kardashian. A whole 13 years older than her beau, Kim K couldn’t get enough of the hunky actor as she took comfort in his arms after the breakdown of her marriage to rapper Kanye West.

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It seems it’s just a case of Davidson being a rebound, as the relationship between him and Kim K came to a screeching halt only nine months after it began. While Pete doesn’t seem to be too bothered or heartbroken by the breakup, we do wonder if it was a publicity stunt for Kim’s reality show, Keeping Up With the Kardashians.

Vincent Kartheiser and Alexis Bledel

The set of Mad Man was the meeting place of Vincent Kartheiser and his Gilmore Girls ex-wife Alexis Bledel. While Bledel is known for her unique beauty and youthful features, the relationship seemed like a fairly happy one that saw the pair tying the knot in 2014 after two years of dating.

Instagram // @alexis_bledelofficial

A few short years later, the pair welcomed a baby girl. Announcing their divorce in 2022 came as a bit of a shock to the press and fans of the two, but they insist it was an amicable split and they still remain friends as they co-parent their child.

Corey Feldman and Courtney Anne Feldman

Trust the former child star to find love with his bandmate. Having known each other for years, the couple married in 2016 after officially becoming an item only two weeks prior. It seems that all the troubled star needed was a good woman to kick him into shape as Feldman returned to acting.

Facebook // Corey Feldman

Feldman might have been a big hit among fans in the ’80s, but his looks all but faded as he grew up. Still, he seems to make his wife Courtney happy, and that’s all that matters at the end of the day. Sometimes a relationship is about more than just looks, and for Corey and Courtney, this seems to be the case.

Pete Davidson and Ariana Grande

Serial dater Pete Davidson and singer Ariana Grande dated for a laughable five months back in 2018. Seemingly distraught over the passing of her former boyfriend, Mac Miller, Grande found Davidson unsupportive, putting a strain on their brief relationship.

Instagram // @petedavidson.93

We all know that Pete wasted no time in finding another woman to date, and Ariana took the time to heal and focus on her career before she, too, started dating again and found love in the arms of hunky Dalton Gomez, who she recently married.

Jason Sudeikis and Olivia Wilde

Jason Sudeikis found his perfect match when he met Olivia Wilde in the early 2010s. After dating for a short time, the couple was soon engaged and married not long after they announced their sudden engagement.

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Fast forward to 2020, and all was not well between the nerdy-looking Sudekis and his glamorous wife Olivia Wilde as the two decided to split, finalizing their divorce in 2020. Following a nasty, very public custody battle over their two kids, the two are said to be amicable and working together to co-parent their children.

Ben Foster and Laura Prepon

Orange Is the New Black star Laura Prepon first met her husband when she was only 18 years old. It would, however, take another few decades before the two would eventually get together, with average-looking Foster proposing to Prepon in 2017. The couple welcomed a baby soon after, and the pair tied the knot in 2018.

Instagram // @lauraprepon

Now the parents of two children, the couple is still very much in love as they share their lives together in married bliss. Laura Prepon found her Prince Charming, giving women around the world hope that their Mr. Right is out there, even if he doesn’t have the looks of a prince.

Michael Sheen and Anna Lundberg

Michael Sheen finally found his happily ever after when he met and ultimately fell in love with Swedish actress Anna Lundberg. Together since 2019, the couple has two children together but are yet to make it official and exchange wedding vows.

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Sheen and Lundberg have a 25-year age gap between them, which has certainly raised a few eyebrows, with critics thinking he’s dating someone completely out of his league. But, as you can see from this recent picture of the two together, they both have that special twinkle in their eye that only true love can bring.

Marc Anthony and Jennifer Lopez

Jennifer Lopez had all but given up hope on ever meeting “the one” when she started dating singer Marc Anthony. After a very short dating period, the couple married in a lavish ceremony in 2004, despite many rumors that Anthony was somewhat of a philanderer that would go on to break J-Lo’s heart.

Flickr // Ana Gremard

The pair welcomed twins Emme and Max in 2008 and separated three years later in 2011. Again, rumors of an affair were raised, and much to the relief of Lopez’s fans and family, the divorce was finalized in 2014. Jennifer has once again found love in the arms of her former beau Ben Affleck who, in our opinion, is a better match for the beautiful Jen.

Andrew Garfield and Christine Gabel

Spiderman actor Andrew Garfield might be talented on the big screen, but his love life is anything but, as he recently came out of a relationship with model Christine Gabel. The pair met and started dating in 2019. While the 11-year age difference was a concern for fans and critics alike, the relationship seemed happy enough.

Twitter // @Garfield_BRA

There’s no clear reason why Garfield and Gabel’s relationship didn’t work out. And like many things in Hollywood, we’ll never know. But one thing is clear in that Gabel always looked like she was way out of Garfield’s league. What do you think?

Griffin Guess and Marissa Miller

Griffin Guess has a lot to be grateful for when you see pictures of the music producer alongside his stunning wife, former Victoria’s Secret model, Marissa Miller. Having met in 2005, the couple dated for a year before tying the knot in 2005.

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Things seem to be going rather well for the unlikely couple, as they welcomed their first child in 2012 and the second in 2015. Only time will tell what’s in store for this couple, and we’re hoping that whatever it is, they stay together forever.

Noah Centineo and Alexis Ren

Once considered a hunky newcomer to Hollywood, Noah Centineo’s looks have somewhat faded. This hasn’t, however, stopped him from dating a bevy of beautiful girls, the most recent being influencer Alexis Ren. The couple started dating in 2020.

Instagram // @alexishernoah

While they were only together for 10 months, the relationship had teen girls crying into their pillows at night. We’ll forgive Noah Centineo for shaving his hair off because he decided to grow it out again. We guarantee this will give him the upper hand in the relationship and have people wondering how his next girlfriend managed to snag such a hottie.

David Cross and Amber Tamlyn

A chance meeting on a flight from Houston to Louisiana in 2007 was all it took for Amber Tamlyn to find love with actor and comedian David Cross. The actor might be 19 years her senior, but this is no barrier for the couple who tied the knot in 2012.

Facebook // David Cross

Tamlyn is said to be smitten with the older man. While it’s led to many questioning just how he managed to get a younger woman as gorgeous as Tamlyn to marry him, you’ll be surprised to know that it was she who pursued him! The couple is still happily married today and has a daughter.

Michael Sheen and Kate Beckinsale

Michael makes the list for his relationship with bombshell actress Kate Beckinsale. The couple met in 1995 and had their daughter in 1999. After a romance spanning eight years, Beckinsale and Sheen split in 2003 and were never married.

Instagram // @katebeckinsale

Sheen has been linked to many gorgeous women in the past, and if his history is anything to go by, he’ll continue to meet and date many more beautiful women before he ties the knot. Kate Beckinsale, too, has moved on and has recently been linked to musician Goody Grace.

Dax Shepard and Kristen Bell

Funnyman Dax Shepard fell head over heels in love with former Veronica Mars actress Kristen Bell in early 2007 when the pair started dating. Pretty much average-looking, critics made bets on how long the relationship between Shepard and the blonde bombshell Bell would last. But, it’s Dax Shepard who would have the last laugh.

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Dax and Kristen have been happily married since 2013. They’re currently focused on growing their respective careers while juggling marriage and two kids. Whatever they’re doing, it works, and the couple still seems very much in love.

Geoffrey Arend and Christina Hendricks

500 Days of Summer actor Geoffrey Arend met and married Mad Men star Christina Hendricks in 2009. Often pictured looking smitten with each other, something just fell off between the two, leaving people wondering why they were together in the first place.

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Was it a case of “love is blind?” Or were the two truly happy? Guess we’ll never know the truth as the pair split in 2019. They cited irreconcilable differences as the cause for the split. We know you can do so much better, Christina. We hope you find someone that matches your good looks.

Ben Stiller and Christine Taylor

Ben Stiller and Christine Taylor met in the late 1990s. After a short stint dating, they got married in 2000. The marriage would last 17 years and see the couple welcome two children. Sadly, they split up in 2017. Fast forward to today, and the happy couple are back together again.

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They’re now focused on getting their relationship back to what it was. The two are happy and excited about what the not-too-distant future might have in store for them.

Ryan Dorsey and Naya Rivera

The relationship between Big Sky actor Ryan Dorsey and the beautiful Glee actress Naya Rivera seemed doomed from the start. After a whirlwind marriage, the couple said their “I dos” in 2014, welcoming a son together before finalizing their divorce in 2018.

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Sadly, Naya Rivera tragically passed away in 2020, leaving her ex-husband to raise their child alone. While the reason for their split was never made public, Dorsey only had good things to say about his ex-wife. He said he still loved her and would raise their son to remember the good things about his mother.

Lee Kirk and Jenna Fischer

It would seem that Pam from the hit show The Office finally found her guy when she married screenwriter Lee Kirk in early 2010. Welcoming a son in 2011 and a daughter in 2014, the couple is still happily married today.

Shutterstock // Kathy Hutchins

While Kirk is not a bad-looking fellow, Jenna’s fans always secretly hoped that she would end up with her The Office co-star John Krasinski. Imagine the beautiful children the handsome couple would produce! Looks aside, the couple is happier than ever.