Awesome Conversation Starters

Everyone knows by now that “Come here often?” doesn’t cut it when it comes to kick-starting a conversation. Never fear, tongue-tied friends: We’ve got a comedian, a former ambassador, a hairdresser, and others willing to spill their tips on chatting up (and dazzling) just about anyone.  You’ll find their useful advice below but first check this out:

Looking to get to know your date better? Running out of things to talk to your sweetie about? First date jitters and don’t know what to talk about? Well, here are 100 questions that can break the ice and get a conversation going. The most important thing is to have fun! You might be surprised by what you learn about the other person. Don’t force anyone to answer a question they don’t want to and don’t pry deeper if they are not willing to talk about a certain subject.

1. What was your best job?

2. What were your worst jobs?

3. Tell me all the places you worked

4. Tell me about your best friend

5. Tell me about your family

6. Tell me about your relatives

7. What was your first car?

8. Favorite movie star?

9. Favorite entertainer?

10. Favorite song?

11. What were your life changing moments?

12. First girlfriend/boyfriend?

13. First kiss?

14. What is the dumbest thing you have ever done?

15. Have you ever been arrested?

16. Political affiliation?

17. Have you voted for someone you wished you hadn’t?

18. Have you used drugs?

19. Do you like to shop?

20. Best way to relax?

21. Favorite thing to do alone?

22. Ever had a one night stand?

23. Do you save money?

24. What hobbies to you spend money on?

25. If you found a $100 what would you do?

26. Do you want children/more children?

27. Are you a good parent?

28. What makes a good parent?

29. Are you romantic?

30. Ever loose a pet?

31. Dog or cat?

32. Pets growing up?

33. Sleep in the nude?

34. Favorite midnight snack?

35. Do you exercise?

36. Did you ever see your parents making love?

37. Peanut butter and what?

38. What is one food you will never give up?

39. What is a food you can live without?

40. Favorite drink?

41. Perfect day?

42. How many cds do you own?

43. How many dvds to you own?

44. Favorite thing to spend money on?

45. What is the weirdest thing about you?

46. What is on your bedside table?

47. Are you cheap or thrifty?

48. Ever been in love with 2 people at the same time?

49. Grades in high school?

50. Favorite teacher?

51. Relatives in jail?

52. Toppings on pizza?

53. Black or white?

54. Glass half full or half empty?

55. Ever been to a food shelf?

56. Ever milked a cow?

57. Ever tipped a cow?

58. Bath or shower?

59. Mountains or the beach?

60. Plane, train or automobile?

61. Favorite all time movie?

62. Worse movie you have ever seen?

63. Best concert you have been to?

64. Beer, wine or coffee?

65. Best vacation?

66. If you could retire tomorrow what would you do?

67. Worse vacation?

68. Three places you would love to visit?

69. Worse boss?

70. If you could do anything what would it be?

71. Super powers you wish you had?

72. Ever had a massage?

73. Ideal romantic dinner?

74. Dumbest purchase you ever made?

75. Where did you find money when you were flat broke?

76. Ever sold blood?

77. What sporting event/concert/entertainment would you buy tickets to regardless of price?

78. Ever hit a jackpot on a slot machine?

79. Ever won the lottery?

80. What would you do with your lottery winnings?

81. Are you a neat freak?

82. Can’t stand being around people who_________?

83. Crowds or small groups?

84. How old do you want to live to?

85. Loose your sight or hearing?

86. Ever had a crush on a member of the same sex?

87. Pet peeves?

88. Most annoying habit?

89. Sexiest parts of a member of the opposite sex?

90. Major turn offs?

91. Tattoos?

93. Piercings?

94. Plastic surgery–would you/have you?

95. Computer geek?

96. Trekee?

97. Play an instrument?

98. Been in a band?

99. Most embarrassing moment?

100. Nude beach yes or no

More great dating ideas and advice can be found around here so browse around and read on!


Denise Fennell, stand-up comic and lead actress from the Off-Broadway hit,Tony n’ Tina’s Wedding
“The art of what I do, as far as improv, is about initiating conversation with strangers. I look at someone and try to find something on his or her body that I can connect with; I look at clothes — shoes, ties, whatever. I think guys find it endearing if you say something like, ‘I bought my dad the same shirt.’ It’s less of a come-on that way. I also think girls can get away with sillier things. I’ll stare at people until they notice me and say, ‘What are you looking at?’ and it totally works in terms of breaking the ice. You have to realize that the worst thing that can happen is he (or she) won’t respond and then you didn’t have a chance anyway — so you’ve got nothing to lose.”

Cristophe, celebrity hairdresser to Bill Clinton, Nicole Kidman, and Liv Tyler

“Don’t play it cool. Being intimidating and aloof is no way to start a dialogue, or a relationship. Being casual and friendly goes a long way towards establishing trust with someone. Also, use the fact that everyone has an image or fantasy of who they are inside. Tell the person he or she reminds you of a certain celebrity and maybe continue the conversation by asking, ‘If you could be any celebrity, who would it be?’ You’d be surprised by some of the answers you might get! It taps into who a person really feels he or she is, or aspires to be. It’s about finding out what someone’s dreams may be. Then you can start connecting.”

Jill Kargman and Carrie Karasyov, socialites and coauthors of the book, Wolves in Chic Clothing
Jill: “Eavesdropping can be a clever entry point into a conversation. Let’s call it the ‘accidental eavesdrop’ because you don’t want to be rude. But especially somewhere like New York, where people are literally on top of each other, it’s easy to overhear something and join in with something fun and clever. It’s a good tactic.”
Carrie: “Do something crazy with your girlfriends. My friends and I used to play a game where one of us would go up to a guy the other thought was cute and say, ‘My friend over there is psychic and we can prove it.’ We had a whole system worked out, but the guys would go along because they’re always up for an outrageous story.”

Danny Millan, owner of Where Brooklyn At! clothing company and former NYC lounge owner
“Treat the person you want to talk to as a human being — as opposed to someone you’re trying to pick up. You can just say, ‘I’m not trying to hit on you, but you’ve got a beautiful smile.’ And if that’s the end of the conversation, let it be the end of the conversation. Be respectful and don’t force it. Everyone appreciates being told something nice, no strings attached. Be earnest, give a real compliment, and maintain eye contact when you’re talking. Women are very quick to pick up on these nuances.”

Donald P. Gregg, former ambassador to South Korea
“I think showing you have a sense of humor is a real door-opener. A willingness to be self-deprecating is often helpful. And remember that sometimes it’s a question of not saying too much — not falling all over yourself. Being low-key is good. And remember: staring over your shoulder or looking beyond the person you’re talking to as if to see who else is there — that’s a killer.”

Dr. Joy Browne, clinical psychologist, syndicated national radio show host and author of Dating for Dummies
“Pick something in the environment around you that you can comment on; for example, say, ‘Isn’t that the ugliest painting you ever saw?’ It’s something another person can focus on, comment on, and it’s also non-threatening. Or just be bold! Once I was invited to a party. I walked in and there were about 50 women — attractive, smart, well-dressed — but virtually no men. I walked up to the little cluster of men and said, ‘My friends and I are over there in the back, and they triple-dog-dared me to invite you guys over.’ The worst that someone can say is no, but so what?”

Paula Froelich, columnist for the New York Post and author of It!: Nine Secrets of the Rich and Famous That’ll Take You To the Top
“Start with a compliment; there just aren’t enough compliments going around. A guy once looked at me and said, ‘I’m sorry to interrupt, but I just want to tell you I think you are really beautiful.’ It was short, simple and sweet and I was so flattered I was speechless, which rarely happens. But make sure it’s sincere and honest. Having a good conversation is about finding common ground, and that requires listening. You may only be interested in his or her body, but you won’t get any closer to the body if you don’t work the brain.”


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