20 Celebrity Dating Stories That Make Us Swoon (And 5 That Were Totally Awks)

Who else loves a romantic, fairytale celebrity love story? Raise all those hands! Don’t lie, you love keeping up with your favorite celebrity couple. Whether they are going on extravagant dates, rocking the red carpet, or hanging out incognito on the streets, they are just so amazingly cute together! Believe it or not, celebrities really are just like us in the dating world. Some meet people on blind dates or on the social media. Others feel that “love at first sight” that everyone talks so much about. Then there are the ones with totally terrible stories. See, just like us!

Once they’re in a relationship, that relationship is also super relatable. Yes, they have the money for date nights we can’t even imagine, but they can also have their fair share of nights on the couch watching TV. Don’t worry, they also have their share of fights and disagreements. The lives of celebrities are so public, that we are lucky enough to get some of the inside scoops when it comes to their relationships. We have put together 20 celebrity dating stories that will make you completely swoon and 5 that were totally awkward! With these stories, you can go out and find your dream relationship, learn something about the one you’re in, or know what to completely avoid!

Continue scrolling to keep reading

Click the button below to start this article in quick view

Start Now

25 Swoon: Blake Lively And Ryan Reynold's Blind Date

First up, we have one of Hollywood’s most famous, attractive, and hilarious duos! What you might not know about their relationship is they might on a blind date...with other people! According to Reynolds, it was a very awkward date for the two other people because he and Blake just had “fireworks coming across.” How magical! The two have now been married for almost six years and have two daughters together. Who knows, maybe your next blind date will bring some surprise fireworks!

24 Swoon: Mila Kunis' First Kiss

Many of us know that Mila Kunis and Ashton Kutcher are another amazing A-list celebrity couple, but some don’t know that Ashton was actually Mila’s very first kiss! When Mila was only 14 years old, she played Ashton’s love interest on “That 70’s Show.” Ashton claims the experience was very awkward and Kunis recalls the teenage crush she had on him! All turned out well for the two. They have been married for three years and have two children together. Not gonna lie though, we kinda wish Ashton was our first kiss!

23 Swoon: Chrissy Teigen And John Legend's First Hang Out

Time for another very well-known Hollywood power couple. Chrissy Teigen has no problem being honest! This includes her story about how she met her husband, John Legend. They met on the set of his music video for the song “Stereo.” She walked into his dressing room while he was ironing his underwear! It sounds awkward, but Chrissy loved it. That night they enjoyed In N Out burgers and the rest is history! They have now been married for almost five years and just welcomed their second child. Think of this story the next time you see one of Chrissy's hilarious and adorable posts about her family!

22 Swoon: Ellen DeGeneres' 60th Birthday Gift

Our next awesome celebrity couple knows all about the importance of supporting their partner’s passions in life. Everyone’s favorite talk-show host, Ellen DeGeneres, turned 60 this year and her wife of 10 years, actress Portia De Rossi, got her one amazing gift! The two traveled to Africa to help build a campus for the Dian Fossey Gorilla Fund. They saw plenty of other animals, including elephants and giraffes, while on their trip. Ellen claims it was the “best gift anyone could have given her.” We’re not crying, you’re crying!

21 Awkward: Amy Schumer's Food Poisoning

Amy Schumer is not shy when it comes to many things! In an interview, she told a story of a trip her and her then-boyfriend, Ben Hanisch, took to France. It was their one-year anniversary and they were ready for some romance. Sadly, they both got a bad case of food poisoning! She ended up being hospitalized. What a way to spend your anniversary! She joked that she knew the relationship was over after that. The couple eventually split and Amy is now happily married. There are really some things you just can’t get over!

20 Swoon: David Beckham's Favorite Music Video

What word comes to mind when you think of David and Victoria Beckham? Classy? Perfection? Both of those apply to this glamorous couple! Their love story involves a music video and love at first sight. David claims he knew she was the one when he saw her in the Spice Girls video “Say You’ll Be There.” He even told his teammate that she was the girl for him! She fell for him literally right away in the Manchester United Players’ Lounge. They have been married for a whopping 19 years and have four children. Talk about the perfect celebrity fairy tale!

19 Swoon: Ariana Grande's Modern Young Love

If you haven’t heard about this couple, you’ve probably been living under a rock. Singer Ariana Grande and comedian Pete Davidson are all over Hollywood news right now. Their whirlwind romance is filled with all the things young love has to offer. There’s an engagement ring worth $93,000, late-night pizza dates, and he even got two Ariana-inspired tattoos! The best part is they say the cutest things about each other! Pete says he feels like “he’s won a contest” and “has never met anyone like her.” How adorable!

18 Swoon: Justin Timberlake's Persistence

Justin Timberlake and Jessica Biel are yet another one of Hollywood’s perfect A-list couples. Most of you probably have a huge crush on Mr. Timberlake! Well, imagine if he had a huge crush on you! That’s what happened with him and Jessica. He tried calling her and she was not into it at first, but he was persistent. They basically fell in love on their first date! He knew what he wanted! What makes this story even better is Jessica really didn’t like the bank *NSYNC! It worked out well though. The two have been married for almost six years and have one son. Who knows, that guy you’re avoiding calls from could be the one!

17 Swoon: Kylie Jenner's Festival Love

There were a lot of big news stories this year. One of which was the birth of Kylie Jenner’s baby! Have you ever wondered how she met her boyfriend, Travis Scott? They actually met when he was performing at Coachella in 2017. They hit it off at a party and Kylie packed her bags and went on tour with him! Talk about a whirlwind! Fast forward to 2018, the couple is still going strong and they welcomed baby Stormi into the world! Maybe you’ll find your next beau on stage at the next festival you attend!

16 Awkward: Taylor Swift's 27-Second Phone Call

Young love can be an amazing thing, but it can lead to some terrible heartbreak! Just ask Taylor Swift. She is the master when it comes to heartbreak jams! She is very open about her past relationships. This includes her relationship with singer Joe Jonas. Taylor says that not only did her breakup with her over the phone, but it was only a 27-second long call! How does that even happen?! Rumor has it, her song “Forever and Always” is about Joe! The two are going strong with their current beaus, so all is well! Take note though, if you’re going to break up by phone, make it longer than 27 seconds!

15 Swoon: Jada Pinkett Smith's Audition

All you 90’s children know the importance of Will Smith! Did you know that his relationship with his wife, Jada Pinkett, all started because of “The Fresh Prince of Bel-Air?!” Jada was auditioning to be Will’s character’s girlfriend, but she was too short! They became friends anyways and the rest is history! They have been married for 11 years and have two children that are also actors! Jada believes they wouldn’t be where they are now if she hadn't auditioned for the part. Their story is a prime example that everything happens for a reason!

14 Swoon: Steve Carrell's Improv Class

Fans of the U.S. version of The Office know Steve Carrell as the crazy boss, Michael Scott. But do you remember Carol from the earlier seasons? Fun fact, that is Steve’s wife in real life! Her name is Nancy Carell and the two are adorable together! They met while Steve was teaching an improv class. Steve was hesitant and nervous to ask her out and Nancy was very quiet around him. Very surprising for two amazing comedians! They eventually got over their mutual shyness and have now been married for 23 years! Steve has been quoted saying him and his wife share the same sense of humor. That must be so important in their obviously very strong marriage!

13 Swoon: Kate Moss's Google Search

Technology has brought us so many new ways to meet new people and potential partners, just ask Kate Moss! We can’t tell you why the beautiful supermodel had to “google men”, but it worked for her! She did a simple Google search and found her rocker husband Jamie Hince. She claims she fell in love right away and they love all the same things! They got married in 2011, but sadly divorced in 2016. Don’t let that discourage you, time to get your Google on!

12 Swoon: Matt Damon's Look Across A Crowded Room

This next story is a prime example of just getting out there! A-list actor Matt Damon was filming a movie in Miami and his friends insisted he go out with them. He really didn’t feel like it but went anyways. He saw the bartender, now his wife Luciana, from across the room and literally fell in love. Talk about fate! They have now been married for almost 13 years and they have three children. What is it with these stars and their looks from across the room and how do we find some?!

11 Awkward: Nicole Kidman's Kinda Quiet (Kinda Famous) Date


This one is pretty hilarious! It involves one of your favorite actresses, Nicole Kidman, and one of your favorite TV hosts, Jimmy Fallon. Fun fact, Nicole had a pretty big crush on Jimmy and asked to hang out. Jimmy apparently didn’t know it was a date! He was awkwardly quiet the whole time. She even asked him out again and he said no! The two were, thankfully, able to laugh it off on his show. We’re happy to hear that such awkward, terrible date stories can end with laughter and friendship!

10 Swoon: Julianne Hough's Ring Size

Get ready because this story is adorable! If you know anything about Julianne Hough, you know she is an amazing and beautiful dancer, singer, and actress. Last year, she got married to the hunky hockey player, Brooks Laich. In an Instagram video, Julianne discussed how Brooks knew he was going to marry her before they even started dating! He even, somehow, figured out her ring size! When you know, you know! We can’t help but love this adorable couple and Brooks’ intuition when it comes to love!

9 Swoon: Kanye West And Kim Kardashian's Personal Baseball Stadium

This next couple includes two of the biggest names in Hollywood, so you know they’ve got an extravagantly romantic story! Kim Kardashian and Kanye West got engaged in 2013. Kanye whisked his woman away to San Francisco. This would be romantic enough for us, but Kanye took it one step further. He rented out AT&T Park, home of the San Francisco Giants, and had “Pleeease Marry Meee!!!” written out on the Jumbotron! How amazing is that?! The two wed in 2014 and have two children together. Their engagement is proof that grand gestures are still a great way to get to a woman’s heart!

8 Swoon: Neil Patrick Harris' Hunky Husband

Those of you who have seen Neil Patrick Harris and his husband David Burtka’s adorable family, you have probably wondered how you reach those couple goals! Well, at the time, NPH was thinking he would be alone forever. We all know that feeling! He was meeting up with a friend who happened to bring along another friend, who happened to be David Burtka. David’s thought was that he would “really like to know him.” He even remembers the intersection they met at. Wouldn’t you love being with someone that has such fond memories of meeting you? The two have been married for almost 4 years and have the most adorable twins. If you haven’t already, google their yearly Halloween costumes. You might not be able to handle the love and cuteness!

7 Swoon: John Krasinski's Favorite Movie

You might know these two from some of your favorite TV shows and movies because they are both phenomenal actors! John Krasinski and Emily Blunt have so many cute little love stories. Most of which revolve around how obsessed John is with his wife, in the best way! He admits to watching Emily’s film, The Devil Wears Prada, at least 75 times! 50 of those were before they even met! She also almost caught him watching it when they first started dating. Eventually, he let her know his obsession and everything turned out fine. They have been married for eight years and have two children. We can only hope for someone that loves us as much as John loves Emily!

6 Awkward: Justin Bieber's Spaghetti Incident

Picture this, you’re on a date with Justin Bieber, one of the biggest celebrities! He takes you to an awesome Italian restaurant. Things are going great, then all of a sudden, there is spaghetti all over you! How embarrassing...especially for him! Justin claims he and his date never went out again. Don’t worry, he is now happily engaged to model Hailey Baldwin. But it t looks like, in Justin’s case, sometimes love doesn’t last with spilled spaghetti and a big dry-cleaning bill!

5 Swoon: Meghan Trainor's Bowling Date


Time for one of the most relatable date stories on the list. We all know Meghan Trainor from her super catchy songs about love! But did you know how she met current fiance, Daryl Sabara? The two went on a double date to the bowling alley and did karaoke on their first date! How fun does that sound?! Towards the end of the date, Meghan asked her security to give her a minute alone. She and Daryl shared a very memorable kiss and that was that! The two have been engaged since December of 2017. This is a friendly reminder that sometimes the best dates are the most simple and fun.

4 Swoon: Viola Davis' Dream Man

Have you ever wanted to meet your “person” so badly that you literally pray? You just want some power somewhere to send someone your way! This actually happened to Academy Award-winning actress Viola Davis. She says she was the “loneliest woman in the world” and she prayed for a man who had all the characteristics she wanted. Three weeks later, she met him! They shared a scene on a television show and explored Los Angeles together. They have now been married for 15 years! If you’re looking for “the one”, you might just need to have a little faith!

3 Swoon: Carey Mulligan's Childhood Pen Pal


If you had a childhood pen pal, chances are it never became anything more than a friendship and exchanging letters. This is not the case for actress Carey Mulligan and her husband, singer Marcus Mumford. They both attended a church camp around the age of 12 and were pen pals! They rekindled their friendship later in life and have now been married for 6 years. Get this, with their busy schedules, they keep in touch by writing letters! What a wonderful and personal way to keep in touch. Who wouldn’t want to write love letters to the person they love?!

2 Swoon: Joanna Gaines' Dad's Auto Shop

HGTV lovers, it is time for your favorite couple! Chip and Joanna Gaines are the do-it-yourself couple that you wish you were a part of. The way they met is one of the cutest! Joanna was working at her dad’s auto shop in Texas. Chip came in and saw her picture behind the counter and claimed he knew he would marry her just from that picture. Go ahead, wipe the tears from your eyes! He eventually asked her on a date but ended up being an hour and a half late. What?! Joanna didn’t seem to mind. The two wed back in 2003 and have five children. What a great example of following your heart!

1 Awkward: Kelly Osbourne's Broken Wrist

How terrible does breaking a bone sound while on a date? Not great is the answer and Kelly Osbourne knows all about it! She was 16 years old when she went on a date in some high-heeled Louboutins. This already sounds like a bad idea. Her date went in for a kiss and Kelly backed up, falling down some stairs and onto the street. Ouch! She broke her wrist and then literally ran away from her date. What a story!

References: People.com, Usmagazine.com, Dailymail.co.uk, Eonline.com, Bustle.com

More in Entertainment