50 Difficult Trivia Questions to Impress, Quiz, and Test Your Family & Friends

With Thanksgiving and Friendsgiving right around the corner, the gathering preparations are in full effect. From curating the perfect menu filled with classics and new recipes to finalizing the perfect seating chart, the holiday season is a perfect opportunity to incorporate a fun trivia game to keep the conversation at the dinner table flowing.

Card games such as Yung Miami’s bestselling Resha Roulette can spice things up with provocative dares and never-have-I-ever-style questions. While not exactly the usual trivia, this is a fun time once the drinks begin to flow. However, for a traditional Thanksgiving, Resha Roulette may not be the most appropriate if grandma is sitting next to you. Therefore, keeping things family-friendly is still a fun option, going around the table to test your loved ones’ knowledge of you, history and any other life component. Even if you plan on having friends over for a casual kickback, there’s nothing like quizzing your pals and hearing the banter that erupts in the room. Here are a few difficult trivia questions to impress everyone during your next get-together.

Sports Questions

1. Who was the first player to win an NFL MVP? (Jim Brown, Cleveland Browns, 1957)
2. Who was the first baseball player to hit a home run? (Ross Barnes of the Chicago White Stockings, now the Chicago Cubs, 1876)
3. What year did Michael Jordan win his first ring? (1991, Chicago Bulls)
4. Which player currently has the most touchdowns in NFL history? (Jerry Rice, 208)
5. When was Floyd Mayweather’s last boxing match? (June 2023 against John Gotti III)
6. What number does Damian Lillard currently wear? (0, Milwaukee Bucks)
7. Who is considered the “Father of Basketball Coaching?” (James Naismith)
8. How many interceptions did Patrick Mahomes have in his rookie year? (0)
9. Which performing-enhancing drugs was Alexander Emmanuel Rodriguez (A-Rod) accused of using? (testosterone and Primobolan)
10. Name at least one of the oldest living professional NBA players. (Bailey Howell, 87)

Personal Romance Questions

These aren’t difficult trivia questions that bank on you knowing your stuff in the realm of sports or history. Rather, you’ll have to know the person who’s asking fairly well. These can be tricky, but they can also lead to some interesting conversations.

1. Who was my first kiss?
2. When did I break up with my first boyfriend?
3. Which person did I ghost and never spoke to again?
4. Who was my favorite boyfriend/girlfriend, and why?
5. What was the name of the guy who I ghosted for having bad breath?
6. Who is the last person I mentioned having a crush on?
7. Who was my favorite sneaky link?
8. How long did my last situationship last?
9. What is the name of the person I dated five years ago?
10. When did I predict I would get married?

Music Questions

1. What was Cher’s first number-one hit? (“I Got You Babe” with Sonny Bono, 1965)
2. How old was Tina Turner when she released “What’s Love Got to Do With It? (44, 1984)
3. What year did Dolly Parton release her first album? (1967, “Hello, I’m Dolly”)
4. Name three one-hit wonders from the 90s (Sir Mix-a-Lot, Mark Morrison, Vanilla Ice)
5. Which album is considered Adele’s “divorce” album? (30, 2021)
6. What year did TLC call out the music industry during an award show? (1996 Grammy Awards)
7. How many times has Beyoncé been nominated for Album of the Year at the Grammys? (3)
8. On what records did Jennifer Lopez use Ashanti’s vocals? (“Ain’t It Funny” and “I’m Real”)
9. When was the first American Music Award ceremony held? (February 19, 1974)
10. Who produced the Waiting to Exhale soundtrack? (Babyface)

Personal Career Questions

1. Which co-worker do I hate at my job and why?
2. Why did I get passed up for my last promotion?
3. What was the name of the company that I quit without notice?
4. Do you remember the name of the co-worker I had a workplace fling with?
5. What was the first thing I purchased when I got my latest raise?
6. What year did I land my first fast-food job?
7. Do you remember the name of the first job I had?
8. At what age did I start working?
9. What is my favorite color to wear to work each day?
10. How many pairs of black dress slacks do I own?

Fashion Questions

1. What year did Naomi Campbell walk her first runway? (1986, designer Jasper Conran)
2. Name two fashion shows that Tyra Banks has walked in. (Victoria’s Secret and Chanel)
3. What was the name of the Chinese designer that Cardi B forgot the name of after he designed her gown? (Sensen Lii from the label “Windowsen”)
4. Who has the most American Vogue covers? (Lauren Hutton, 27)
5. True or false: Crocs and Balenciaga collaborated for a collection. (True)
6. Name three Black 90s artists who modeled for Tommy Hilfiger. (Mary J Blige, Usher, Aaliyah)
7. Which designer created the famous black sparkly boots Beyonce wore during the Renaissance tour? (Marc Jacobs, Kiki Boots)
8. What was the name of Nelly’s first fashion line? (Vokal)
9. When were Timberland boots introduced? (1973)
10. When did the fashion brand True Religion begin? (2002)

Difficult trivia questions aren’t just a great way to give your brain a workout — they’re also a great way to get everyone in the room talking, guessing, laughing, and maybe even disagreeing on the answers. Give these a try the next time you need to break the ice and keep the conversations going.

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