Dating can be so difficult in this day and age. It’s hard enough to: 
  • find someone on line that you are attracted to 
  • then getting them to chat with you, 
  • then keep the chat going, 
  • then trying to meet them,  
  • then having to wait until that meet, 
  • then be attracted to them on the meet, 
  • then getting an actual date, 
  • setting a date for that date,
  • then having to wait until that date,
  • getting a second date,  
  • then having to wait until that date,
  • then trying to find time to date when you decide to date, 
  • then someone not trying to stay in the relationship
Deep breath…It’s hard. 

Number one, cannot be said enough. Listen to your date. 

You’ll actually learn something, about them, and/or about yourself. 

Women love to be heard, that is a promise. If they say they are happy eating tacos, take them for tacos. They will then know they have been heard. We all appreciate being heard. 

Surprisingly, men like to be heard too.

Number two, have questions ready 

Have questions ready, but not too many. You don’t want to come across as if you are interviewing the person.

  1. what’s meaningful to you?
  2. what do you want from some you are dating?
  3. how long have you been separated/divorced?
  4. are you an introvert or extravert?
  5. do you like the arts, music, sports, reading, etc?
  6. do you like to cook?
  7. are you neat or a slob?
  8. which dating site do you like best?
  9. What’s your guilty pleasure food?
  10. Favourite music genre
  11. Who do you admire
  12. What was your first concert ever
  13. What’s the best ticket stub you have stashed in your cigar box?
  14. How much do you hate online dating?
  15. Camp or hotel
  16. Sandals or high heels
  17. Truck or car
  18. Dog or cat
  19. Beer or wine
  20. Levis or designer jeans
  21. Harley or crotch rocket
  22. Beach or casino
  23. Sports or ballet
  24. Do you know who (insert your favourite musician/artist/sports star etc) is? (ex Mick Jaggar)
  25. Mac or PC
  26. Sweet or salty

More question suggestions:

Man Telligence (KyleG)

  1. What Do You Like to Do in Your Free Time?
  2. Who Is the Most Fascinating Person You’ve Met?
  3. What Was the Last Book You Read that you really liked?
  4. What Are Some Movies You Really Enjoyed?
  5. What Amazing Adventures Have You Been On?
  6. What TV Series Do You Keep Coming Back to And Re-Watching?
  7. Among Your Friends, What Are You Best Known For?
  8. What Music Artist Do You Never Get Tired Of?
  9. What Are Some Obscure Things That You Are or Were Really Into?
  10. What Are Some Things Everyone Should Try At Least Once?
  11. What Are You Always Game For?
  12. Where’s the Strangest Place You’ve Ever Been?
  13. Where Would Your Friends or Family Be Most Surprised to Find You?
  14. What Do You Like but Are Kind of Embarrassed to Admit?
  15. If You Could Go Back in Time as An Observer, No One Could See You, And You Couldn’t Interact with Anything, When Would You Want to Go Back To?
  16. What’s Been the Most Significant Plot Twist in Your Own Life?
  17. How Much Social Interaction Is Too Much for You?
  18. What Pets Have You Had?
  19. What’s Your Favorite International Food?
  20. How Many Siblings Do You Have?
  21. Who Is Your Favorite Author?
  22. What Was the Last Show You Binge-Watched?
  23. If There Was an Olympics For Everyday Activities, What Activity Would You Have A Good Chance at Winning A Medal In?
  24. What’s Your Favorite App on Your Phone?
  25. If You Could Give Yourself A Nickname, What Nickname Would You Want People to Call You?
  26. What Country Do You Never Want to Visit?
  27. What Is the Most Beautiful View You’ve Seen?
  28. What Did You Do Last Summer?
  29. What Did You Do For (Last Holiday)? Or What Will You Do For (Next Closest Holiday)?
  30. Best and Worst Flavor Ice Cream?
  31. What TV Shows Did You Watch When You Were A Kid?
  32. If You Opened A Business, What Type of Business Would You Start?
  33. What’s Your Favorite Thing to Do Outdoors? How About Indoors?
  34. What’s the Most Spontaneous Thing You’ve Done?
  35. What’s Your Go-To Funny Story?
  36. What’s Your Favorite Quote or Saying?
  37. If You Unexpectedly Won $, What Would You Spend It On?
  38. Are You A Morning Person or A Night Owl?
  39. What’s Your Favorite Restaurant?
  40. What Would Be Your Dream Job?
  41. What Would Your Perfect Vacation Look Like?
  42. What Would Your Perfect Morning Be Like?
  43. Who Is Your Kind of People?
  44. What Odd Talent Do You Have?
  45. What Would You Like to Know More About, But Haven’t Had the Time to Look into It?
  46. Have You Ever Joined Any Meetup Groups?
  47. What’s the Most Relaxing Situation You Could Imagine?
  48. Where Was Your Favorite Place to Go When You Were A Kid?
  49. If You Found A Briefcase Filled with Million In $ Bills in Front of Your Door, What Would You Do with It?
  50. What’s the Worst Advice Someone Has Given You?
  51. Besides Your Home and Your Work, Where Do You Spend Most of Your Time?
  52. What Do You Care Least About?
  53. What Are People Often Surprised to Learn About You?
  54. What Would You Do with The Extra Time If You Never Had to Sleep?
  55. When You Were A Kid, What Seemed Like the Best Thing About Being A Grown Up?
  56. If You Could Send One Letter to Yourself in The Past Without the Goal of Making Yourself Rich (No Lotto Numbers, Stock Picks, Etc.), What Age Would You Choose and What Would the Letter Say?
  57. How Different Do You Act When You Are with Acquaintances Vs. People You Are Comfortable With?
  58. What’s Your Go-To Series or Movie When You Want to Watch Something but Can’t Find Anything to Watch?
  59. What Do You Like to Eat to Cheer Yourself Up?

Here are funny first date questions to ask:

  • What Fad Did You Never Really Understand?
  • What’s the Silliest Fear You Have?
  • If You Lived To 100, Would You Rather Keep the Body or The Mind of Yourself at Until You Were?
  • What’s the Strangest Phone Conversation You’ve Ever Had?
  • What Machine or Appliance in Your House Aggravates You the Most?
  • What’s the Worst Movie You’ve Ever Seen?
  • What’s the Most Ridiculous Thing You’ve Done Because You Were Bored?
  • What’s Happening Now, That in Years People Will Look Back on And Laugh About?
  • If the Company You Work For / The College You Go to Had an Honest Slogan, What Would It Be?
  • Which Is the Cheesiest Pick Up Line Someone Has Used on You?
  • What Is Your Weirdest “Quirk”?
  • If You Ruled the World, What Would You Change?
  • What Is Something You Have Tried, But Will Never Do Again?
  • What’s the Weirdest Thing You’ve Ever Eaten and Liked?
  • If You Could Be A Man/woman for Just One Day, What Would You Do?
  • What Is the Most Embarrassing Thing That Happened to You in School?

Here are random first date questions:

  • . Cutest Animal? Ugliest Animal?
  • . What’s Your Favorite Piece of Furniture You’ve Ever Owned?
  • . What Household Chore Is Just the Worst?
  • . How Techie Are You?
  • . What’s Expensive but Totally Worth It?
  • . Before You Make A Call, Do You Rehearse What You Are Going to Say?
  • . When Was the Last Time You Sang to Yourself or To Someone Else?
  • . When Was the Last Time You Walked for More Than an Hour?
  • . What Would Make for An Excellent New Ice Cream Flavor?
  • . What’s the Most Interesting Fact You Know?
  • . What’s Your Favorite Smell?
  • . What’s the Most Amount of People You Had to Present Something In Front Of?
  • What’s the Strangest Way You’ve Become Friends with Someone?
  • What Sports Would Be Funniest If the Athletes Had to Be Drunk While Playing?
  • What’s Your Favorite Band NAME (Not Necessarily Your Favorite Band)?
  • How Well Do You Cope When You Don’t Have Your Phone with You for An Extended Period of Time?
  • If You Had the Power to Change One Law, What Law Would You Change?
  • How Would You Feel If You Were in A White Room with People All Dressed in White?
  • If You Had Power to Transform into A Bird, What Type of Bird And Which Bird Would You Want To Become?
  • If You Were in A Forest, What Are the Three Emotions You’d Feel?
  • Do You Squeeze the Toothpaste from The Middle or The End?
  • Have You Ever Felt Like You Met Someone in A Previous Life?
  • If You Could Read Minds, How Would You Use the Gift?

Here are would you rather questions to ask on a first date:

  • Would You Rather Live Full Time in An RV Or Full Time on A Sailboat?
  • Would You Rather Have an Incredibly Fast Car or Incredibly Fast Internet Speed?
  • Would You Rather Have True Love or Win the Lottery?
  • Would You Rather Marry A Nice Guy or A Flirty One?
  • Would You Rather Spend Months Living in A Nursing Home or Spend A Weeks Eating Only From Taco Bell?
  • Would You Rather Go to An Amusement Park or A Family Reunion?
  • Would You Rather Work Behind A Desk or With Your Hands?
  • Would You Rather Be A Hard Worker or A Smart Worker?
  • Would You Rather Live in A Cabin in Alaska Or on A Tropical Island?
  • Would You Rather Have No Sense of Smell, Or Have A Sense So Strong You Could Smell Everything Around You Like It Was in Front of Your Face?
  • Would You Rather Go for A Bungee Jump or Hot Air Balloon Ride?
  • Would You Rather Live for Months in A Light House, Accessible Only by A Mile Boat Ride, Or Live for Months in The Most Crowded Room of A Youth Hostel?
  • Would You Rather Be Able to Stop Time at Will or Age at Half the Normal Human Rate?
  • Would You Rather Be Confined to Your Home for One Month and Only Able to Communicate with The Outside World Via Fax Machine or Unable to Go Back To Your Home For Months?
  • Would You Rather Have Many Causal Friends or One Close One?
  • Would You Rather Have A Mansion or A Cozy Home That Has Just the Right Amount of Room?
  • Would You Rather Have an Exotic Meal in A Five-Star Hotel or A Delicious Chocolate-Cake from A Local Bakery?
  • Would You Rather Be Someone Else’s First Love or Their Last Forever?

Here are deep first date questions to ask:

  1. What Would You Do If Had Enough Money to Not Need A Job?
  2. What Are Some Accomplishments That You Are Really Proud Of?
  3. If You Could Give Everyone Just One Piece of Advice, What Would It Be?
  4. Do You Prefer to Work in A Team or Alone?
  5. How Have You Changed from When You Were in High School?
  6. When Do You Feel Most Out of Place?
  7. What Says the Most About A Person?
  8. If You Could Have the Answer to Any One Question, What Question Would You Want the Answer To?