Use Funny Dating Tips to Break the Ice on the First Date

Edited by Donna, Maria, Eng

Ways to Use Humor Break the Ice On the First Date

Use humor to break the ice on the first date.


Whether it is a blind date, a date arranged because the two of you have been texting each other on social media or a date with someone you have known for some time, dating can sometimes feel a bit awkward. It is mostly because you don't know each other very well and are not sure what to expect.

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Here are some ways that you can break the tension on the first date by using humor.

  1. 1
    Try using a little "water cooler humor" to break the ice by bringing up the news or a late night show host's best jokes from the night before
    .
    Start by asking your date if he or she has seen the news today and then bring up the funniest or most absurd news item that you can think of. Weird news is everywhere today and discussing it using that "Can you believe it?" tone can really help break the ice. You can also refer to the monologues of late night talk show hosts and quote them to make him or her laugh.
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  2. 2
    Start off by telling him or her that you want to conduct a compatibility test by asking a few questions
    .
    Here are some examples of the kind of thing that you want to ask" "What's the best way to hang toilet paper? Under or over?";"You are ordering a pizza. Pineapple or no pineapple?" ; "Gilligan's Island. Who do you like better? Ginger or Maryann?"; "Apple or IBM?" This will not only lead to some quite funny exchanges, but it is also a great way to get to know each other.
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  3. 3
    Ask him or her to describe the worst date they have ever been on
    .
    If this gets you both laughing, then return with your own tale about a terrible date. If this is succeeding in breaking the ice, then go onto asking him or her what the second worst date and what the third worst date was. One caveat with this is to change the topic if he or she starts to talk too much about his or her ex. You do not want to remind the person of unpleasant memories or have the date turn into a confessional.
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  4. 4
    Ask him or her to make a list of the five biggest pet peeves and then you do the same
    .
    If he or she does not respond right away, then begin with your own list. It helps if you make the pet peeve pertain to your present circumstances. For instance, if the service is slow at the restaurant you are at, say something like, "Well number one is slow service at restaurants!" You can think up a humorous pet peeve list at home beforehand, as in, "People who pay for their groceries using dimes and nickels, when there is a line-up at the grocery store," or "People who publish memes about hating memes."
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  5. 5
    Ask, "What was your favorite food as a kid." This is usually a funny answer, you can follow up by asking for a second favorite food, and you can also ask if the person still eats the food today
    .
    Marvel at how weird the food was back then as in, "Can you believe we used to eat whipped cream cheese that came from a spray can?"
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  6. 6
    Ask him or her what the weirdest food he or she has ever eaten and why
    .
    This can turn up some hilarious responses as well as help you to get to know each other better. A typical thing that you might say is, "Dirt. But I was four." Keep it light by funny. If your date says something like "Snails!", you can respond by going "But those are my favorite!"
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  7. 7
    Ask him or her which actor or actress they hate the most and why
    .
    This can be quite humorous and usually leads to an interesting discussion about movies and what the person likes most in pop culture as well.
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  8. 8
    Ask him or her which favorite celebrity you remind them of and why
    .
    Remember to keep your own sense of humor when you get the answer, because it may not always be what you want to hear.
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  9. 9
    Ask him or her what their favorite "worst song" is of all time and why
    .
    The idea here is that the song is too corny to be cool to be liked, yet can be associated with a great memory.
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  10. 10
    Ask him or her what her favorite "worst" bad horror movie and why
    .
    This can draw you both into a conversation about corny old movies and perhaps a discussion to watching one together in the future.
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  11. 11
    Ask him or her what the very worst thing he or she ever did in high school
    .
    This type of question usually leads to a very humorous tale about some wicked hijinks and it can also help reveal the hidden naughty side to your date's character.
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  12. 12
    Ask him or her what he or she would do if they suddenly won a hundred million dollars in the lottery
    .
    Usually, the answer to this question is quite humorous and you can also find out a lot about the other person's dreams and desires and where they see themselves in the future as they answer this.
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  13. 13
    Ask him or her what three things they would bring with them if they were stranded on a desert island
    .
    This usually leads to a funny answer that will have you both laughing, and also gives you an idea of what most matters to the person.
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  14. 14
    Ask him or her what their astrological sign is and if there is one astrological sign in the zodiac that they hate the most or that they seem to think is eviler than another
    .
    Whether they believe in astrology or not, this usually leads to some kind o spirited or lively discussion about "that evil Scorpio" or "two-faced Gemini" that they have known.
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  15. 15
    Keep it simple by telling him or her a joke and then asking if he or she wants to hear another
    .
    Usually, the person will say yes or respond back by telling a joke of their own.
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  16. 16
    If you notice something funny happening around you, point it out immediately
    .
    If a woman has a piece of toilet paper caught on her shoe, then make sure he or she sees it. If a dog walks by wearing a funny pair of boots, point it out. This is known as being aware of situational humor, and being perceptive can help you point it out and make your date laugh.
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  17. 17
    Break the ice with a little self-deprecating humor
    .
    A good example would be, "I don't know about you but I am so bad at parking my car that people beg me to park in the handicapped spot."
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  18. 18
    Try whining a bit, in a good-natured way, about one of the many ills of modern day society
    .
    For instance, "Remember when you would order coffee and there was only small, medium or large. Now you have to speak Italian before you have any idea what size you are getting."
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  19. 19
    If you sense your date is not shy about things, try playing a game of Truth or Dare with him or her
    .
    For this to work, you have to keep the dares non-sexual and within the context of where you are. For instance, you can ask your male date a question such as, "Is that your natural hair color or do you dye it?" If she takes the dare, you can make her pick up a fork off of another table in the restaurant or something similar. Keep the questions a bit personal and the challenges simple and within the context of where you are. A woman could ask a man, "How many women have you ever stood up for a first date?" If he takes the dare, it could be something like, take off both of your shoes and stand up beside the table in your sock feet. Keep in mind that this type of playing around is not for everybody as the game is a bit personal and also a bit immature.
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  20. 20
    When he she goes to the washroom or outside for a minute, text her and go "Miss me yet?" This should make him her smile because it is a bit too early in the relationship for you to be texting something so blatantly out-of-place and inappropriate.
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Tips and Tricks

Sharing a glass of wine together can help life seem a little less serious.


  • Order a cocktail first thing, to help relax your date, put him or her in a better mood, and also make him or her more receptive to your jokes
  • If the person you are about to date does not have a great sense of humor, then you are better to play it straight, as there are people out there that find funny people to be defensive, insecure or even disrespectful
  • Avoid derogatory humor, especially about the other's person's profession or appearance
  • Avoid using sarcasm about anyone or anything, or you could come off a negative or bitter
  • Save the dirty jokes for when you know each other much better
  • One way to avoid having too many long silences and awkward conversations on a first date is to make sure that you are on a date that involves some activity, such as bowling or hiking
  • If you are in a bar or a pub that has trivia games onscreen, this can help start conversations and break the ice
  • Men should keep in mind that women are not that responsive to sexist humor nowadays, as in: "There's something wrong with my bed. You're not in it!"
  • Make sure that any jokes that you do tell sound natural and not like you memorized them from online
  • If he or she is not laughing at your jokes, it means that he or she is finding you annoying, so try being serious instead
  • It is usually best not to try to make your date laugh by making fun of others, as most people find that to be unfair play
  • If you are not so funny yourself, you can also take her to a funny movie or a comedy club, to get you both in a good mood

If you have problems with any of the steps in this article, please ask a question for more help, or post in the comments section below.

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Categories : Dating

Recent edits by: Maria, Donna

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