10 Celebrities Share Their Best Dates And Their Worse

Find out how celebrities get through their best and worse dates

By Michele
10 Celebrities Share Their Best Dates And Their Worse

Just like us, celebrities have their own share of best and worst dates too. Best dates change your life for good for forever and bad dates teach you a lesson for life. That’s a major difference.

Dates go bad, as some people are difficult to understand or are not interested at all. While some people are not actually what they pretend to be. It’s a difficult thing to get connected at once.

But what a blessing it is to click at once –your personalities, sense of humor and way of carrying forward a conversation! Nothing better than this experience!

A List of Celebrities Best and Worse First Dates

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So here we have some interesting date stories that, I am eager to share with you. I hope you will find them entertaining.

Celebrities Best Dates

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A good number of celebrities have dated the right people and eventually made them their partners. What’s better than loving someone and getting loved in return? So, here is what different celebrities have shared.

Tom Brady & Gisele Bündchen

“This friend told me he knew a girl version of me,” Brady told in 2009. “And he said to me he’d found a boy version of me,” added Bündchen. Once face-to-face, the pair knew their friend had been on to something. “I knew Tom was the one straightaway. I could see it in his eyes that he was a man with integrity who believes in the same things I do,” the model told Vogue, recounting the story to Jimmy Fallon in late 2018.

Prince Harry & Meghan Markle

The couple revealed that they were set up on a blind date and knew very little about each other before they met. “It was definitely a set-up — it was a blind date,” Harry said during the couple’s revealing interview. “It was a blind date for sure.”

Emily Blunt and John Krasinski

James decided to take Emily to a shooting range. "On our first date, I decided, 'I'm gonna really hit the gas and bring her to a gun range,'" John told Conan O'Brien in 2012. "I think that I was so sure that I would never end up with her, that she would be like, 'this is ridiculous, I could have anyone, not you,' that I was like, 'you know what, I'm gonna blow it right away,' and then that way you don't feel bad." Even though John tried to show off his macho side, he told Conan that he yelped the first time he fired a gun. Well, it worked these two are now married with two young daughters.

John Legend and Chrissy Teigen

In a very candid interview with Wendy Williams in 2014, Chrissy told the talk show host about her first date with John, which was basically when they filmed a music video together. "We did the music video, we were together for like 12 hours," she said. "We spent the entire day together with me in my underwear and him in a full suit and I went to go say goodbye to him, to his hotel, and we didn't ever say goodbye that night." Years later, the couple is married and more in love than ever, and their daughter, Luna, is possibly one of the cutest babies in the world.

George Stephanopoulos & Ali Wentworth

“We met on a blind date,” Wentworth revealed it on The Tonight Show. “I had a birthday party, all girls, and everyone said, ‘You know, you have to start dating, Ali.’ And I said, ‘you know what, I live in L.A., it’s either agents or actors — I’m not interested. And one of them said, ‘You should go out with my old boyfriend, George Stephanopoulos.’ And I said, ‘No, thank you.'” Luckily, the comedian eventually agreed to meet the journalist.

Celebrities Worst Dates

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Celebrities have often landed themselves in trouble, due to poor decisions or consideration. Well, they must have learned something significant that they won’t be able to forget easily. Let’s see how bad it went for different celebrities.

Britney Spears

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“I have a friend at home and he randomly sets me up with people every now and then on dates. It’s just awkward because there are so many times that you meet people and it’s just too awkward and you just don’t feel right,” she shared on The Jonathan Ross Show. “I went with this one guy and he looked like a lizard. Like I was so scared … I was like, ‘Holy shit, he looks just like a lizard,’ and I had to go immediately.”

Jenny Slate

“I got set up on a blind date by the husband of my best girlfriend, and he set me up with a man that he didn’t know very well and she had never met,” Slate explained. “He comes around the corner inside the restaurant … this dude, and I’m not kidding, is dressed in full chainmail. He’s got a full authentic knight’s costume on, including a floor-length tabard, which I called a tunic and then he corrected me and was like, ‘It’s actually a tabard.” The comedian decided to stick it out for the meal. “I have a whole date with him,” she continued. “His chainmail is like getting caught on stuff.

I am feeling feelings which I never even felt as a teenager, which are like, you’re embarrassing me. I’m mortified, and also just mad. He’s trying my pasta with the chainmail clinking across and stuff, it’s insane.” After saying her goodbyes, Slate decided to nurse her bad date wounds right away: “I went back into the restaurant because I canceled my Lyft and was like; I’m going back inside to get drunk until I die, obviously. I went back in and was so weirded out that I think I ordered whiskey vodka which is not even a drink.”

Ellie Kemper

“The worst [date I’ve been on] was a setup, a blind date,” she shared. “When your friends pick someone out for you, they say, ‘Oh, you’ll like this guy.’ Then you meet him, and you’re going, ‘you thought I would like him?!’ This particular guy was rude and was much older than I was. He seemed pained to be there. I was like, ‘Why would this person even want to go on a date?'

Nikki Reed

“When I was in second grade, I went on a date with this guy. I thought it was a date, but he didn’t,” said Reed. “And I wrote on a piece of paper, ‘Do you want to be my friend or my boyfriend or nothing? Circle one.’ And he circled ‘nothing.’ That was probably my worst date ever!”

Michael Kors

“In my twenties, I went to meet my date at a really chic, fashionable restaurant. I wasn’t dressed up necessarily, but I had a nice shirt and jeans. My date showed up in cutoffs and a tank top,” he recounted. “I knew half the people in the restaurant, who were all looking at me like ‘Who is this guy with Michael Kors?’ It was so embarrassing. My tip: Always have your first date at a casual place.”

5 Best First Dates Venues for Couples

So it's your first date. Everything matters when you are meeting someone for the very first time –clothes, body language, hygiene, venue, and attitude. Before we discuss some attention-grabbing outfits for first dates, let me help you choose an interesting venue that will make your date a special and a memorable one.

1. An Amusement Park

Don’t worry; you will get plenty of hand-holding time in the horror house, the roller coaster or any other similar ride. An amusement park is also a perfect place for knowing each other better; as you will spend considerable time together eating, having fun on the rides and playing games.

2. A Sports Game

A professional league game will cost you too much. So, I advise you to attend any minor league game. At the game, you will have a lot of time to talk to each other, see the players in action and also have some snacks. Minor leagues are not that electrifying hence; you can take it casually and spend more time with your date.

3. A Trivia Night

I think it’s one of the most interesting venues for first dates; as they tend to remain emotionally competitive. Together you can enjoy some drinks and have a good time at the trivia night. During pauses, you can chit-chat and see each other’s hidden intellect.

4. Picnic Spot

If you are up for some adventurous date, then a picnic spot is perhaps the best venue. I highly recommend choosing a secluded and romantic spot, where you can spend a whole day together. Set up a camp, manage your food-spread, light fire and show your inner scout. It can be a lot of fun. Just imagine seeing the sunset together, cooking your food, hearing sounds of nature and being away from the hustle and bustle of the city.

5. Coffee Spot

There is no need to go for any high-end place where you do not feel comfortable. Choose a laidback coffee shop where you can easily talk to each other for a considerable time. Order your favorite coffee and get emotionally connected with each other.

5 Outfits for First Dates

Choosing the right outfit, for your first date, is another challenging task. You have a lot of questions in your mind like: do I look good in this color? Is the fabric fitting well? What type of tops, bottoms and other accessories looks appropriate? Do I look smart in this outfit or not? And a couple of similar questions! Don’t worry anymore; I have saved you from this pre-date madness by picking the right outfit choices for the first date.

1. Long Midi Dress and Casual Sneakers

No, it isn’t too casual! After all, you have to make yourself comfortable too. Wear a decent colored/patterned midi dress and opt for sneakers of the same color or you can even go for a contrast. It’s an ideal outfit; if you are planning to go for a hike or camping or some café.

Tie-Waist Blouse and Short Skirt

There are several printed and embroidered blouses available. Get one that fascinates you the most and is suitable according to the venue that you have mutually decided upon. When it comes to the skirt keep it simple and in one-tone. Let the blouse steal the show. Just don’t make yourself look weird.

Dressy-Blouse and Relaxed Fit Jeans

You got a nice pair of jeans, but don’t know how to dress a little better for the first date? I suggest you go for a dressy-blouse made of velvet or silk. It is a unique combination of elegance and comfort. So, you won’t worry at all about being over or underdressed. There are countless colors and styles that you can choose from. Just keep it well-balanced.

Shirtdress and Chic Heels

Planning your first date after work? Well, then a shirtdress accompanied with chic heels is certainly the right choice. You can skip the hassle of going back to your home and changing. Choose a classic shirtdress according to the weather and wear a heel – probably bright-colored and attractive. It’s a stress-free and comfy outfit for a date.

Boxy Blouse and Leather Skirt

Want to spice your outfit a bit? Alright then, you need to opt for a boxy blouse in one tone – probably a lighter one and a dark colored leather skirt. To further kick it up, wear mid-calf boots of leather too. You are going to certainly rock it!

Related Article: Top 30 Dating Questions for That Mind Boggling First Date​​​​​​​
Top 30 Dating Questions for That Mind Boggling First Date

Make your first date night easy with these top dating questions.


Your first date needs to be the best one, from your side at least. Shower, apply perfume, get dressed properly, choose a peaceful venue and manage everything gracefully. Stay mentally active and don’t get nervous about how you are carrying yourself. Be confident in who you are.

Also, you need to have a positive and friendly attitude; as you are looking for someone to spend time with in the future. Don’t throw yourself all over the place; listen to your date too. Show respect and if you aren’t inclined towards each other know when to politely say ‘No’.

Wishing you all the best for your first date!