100 Conversation Starters for Dating, Making Friends, and Being Social

Making friends, dating, and networking successfully relies heavily on our abilities to communicate with others. Knowing what to say, and what is appropriate to ask in order to get a conversation going, can make or break that first chance we have to make an impression.  Talking to someone we barely know is intimidating to say the least.  I usually don't have this problem, as I am a born talker, however, many people I meet in the large social group I am involved in do not have the social skills needed to get that first conversation going.

So, I made a cheat sheet for you with 100 simple questions to ask someone you just met.  Some of the questions are more appropriate for someone you would like to date rather than someone you met for business, but most of these are pretty useful in any situation!


1. What would your dream vacation entail?
2. What's your favorite thing to do in your spare time?
3. If you could only listen to one song/cd/artist for the rest of your life, which one would it be?
4. Have you ever had a lucid dream?
5. What's more romantic, the top of the Eiffel Tower or a moonlight tropical island?
6. Have you ever been friends with someone you didn't like because it was easy/convenient?
7. If you could learn a new language effortlessly, what would you learn?
8. If you could live a day in the life of any celebrity, who would you pick and why?
9. What's the worst movie you have ever seen?
10. What did you want to grow up to be when you were a kid?
11. What would you wear to a 90's party?
12. Cats or Dogs?
13. If you could leave one lasting impact on the world, what would you want it to be?
14. Have you ever shoplifted anything?
15. What's the craziest thing you and your friends have ever done?
16. If we were to take a road trip right now, what would your dream destination be?
17. How old were you when you had your first kiss?
18. What would you say your signature drink is?
19. If your best friend showed up at a party wearing the same outfit as you, would you be upset?
20. What's your favorite outdoor activity?
21. What's the best concert you've been to?
22. Have you ever had a dream where someone close to you did something that upset you and you woke up angry at them?
23. Did you ever mix pop rocks and coke as a kid?
24. Would you rather fly to an exotic location or take a cruise there?
25. What country is #1 on your list to visit?
26. Have you ever met anyone famous?
27. Would you rather spend a weekend with Aerosmith or Lady Gaga?
28. What's the most trouble you ever got into as a kid?
29. If your life was a movie, who would play you?
30. What's one big thing you want to accomplish in the next 10 years?
31. Do you play any musical instruments?
32. Who's sexier, the lead singer or the drummer?
33. Would you ever travel someone where you couldn't speak the language and no one spoke English?
34. What's you ultimate guilty pleasure?
35. Would you ever sabotage a friend's diet?
36. If you found a wallet full of money lying on the street, would you keep it or try and return it?
37. James Dean or Brad Pitt?
38. Among your friends, which sex and the city character are you?
39. If you had a theme-song, what would it be?
40. Do you know all the words to your national anthem?
41. Why is it that when you have those dreams about being naked at school/work, no one ever offers you some clothes?
42. Would you rather go out on a date with Batman or Superman?
43. What's the craziest fad you've ever followed?
44. What the worst style you've ever worn?
45. Have you ever had a fortune cookie fortune come true?
46. Would you rather spend a week camping or at a spa?
47. What was your favorite cartoon when you were a kid?
48. Would you hang out with Mr. T. if you met him at a bar?
49. What is your all time favorite movie and why?
50. Do you have an embarrassing song that you love to listen to?
51. Do you think Marylin Manson/Eminem listens to his own music?
52. Do you think relationships that start online are stronger or weaker because you get to know each other's interests first?
53. How long after the relationship ends is it OK to make a move on your best friend's ex?
54. Would living in the same city as your parents be a good or bad thing?
55. Do you dream in color?
56. Do you have any strange hobbies like stamp collecting?
57. Did you have a favorite doll as a kid?
58. Did you have a favorite ninja turtle?
59. What's your favorite accent?
60. If you were named ruler of the whole world, what would you do?
61. What was the scariest movie you saw as a kid?
62. Did you have a monster in the closet or under the bed?
63. What's the most embarrassing thing your parents have ever done?
64. If you were in a rock band, what would you play?
65. Who was your first TV crush?
66. Would you rather live somewhere that was always too hot or always too cold?
67. What's your favorite season?
68. What's the meanest trick you ever played on someone?
69. Climbing mountains or scuba diving?
70. Rock and Roll or Pop?
71. Have you ever dumped a friend's boyfriend for her?
72. What era do you wish you had been born in?
73. Who's your favorite fictional character?
74. If cost didn't matter, what would your ideal house look like?
75. What's cooler, surfing or snowboarding?
76. What historical figure would you want to dance with?
77. Did you like the Austin Powers movies?
78. What do you think of tattoos on women?
79. Would you ever go on a reality TV show?
80. What stereotype were you in high school?
81. Do you have a favorite pair of socks?
82. Is smoking still sexy?
83. Skiers or Snowboarders?
84. What is your idea job/occupation?
85. Which is more romantic, Paris or Venice?
86. Would you rather have one true love or an endless stream of lovers?
87. Did you ever have a crush on a famous musician?
88. If the world was going to end tomorrow, what's the one thing you'd have to do today/tonight?
89. Do you think two people can meet and instantly know each other?
90. Do you have a cause you are really passionate about?
91. Would you ever live on an island?
92. If getting your dream job meant moving to the other side of the globe, would you take it?
93. What's your favorite amusement park ride?
94. What's the best book you've ever read?
95. Would you visit ruins that had a reputation of being haunted?
96. Have you ever told a really big lie to a close friend?
97. Would you be comfortable having a butler?
98. Would you rather have a private jet or a private yacht?
99. Would you ever go diving with sharks?
100. If you won 10 million dollars in Vegas, what's the first thing you'd do?


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