How To Mess Up a Dinner Date: A Beginner’s Guide to Dating Misery

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You have a date with someone you find enormously appealing. You don’t actually recall the details of how you happened to make the contact. You were at a party, talked to the woman a bit, and discovered her phone number in your pocket when you got home. You’d had too much to drink, so nothing in your memory bank suggests what you discussed. But, when you called her a few days later, she did agree to have dinner with you.

Now what?

Rather than tell you precisely what to do, I will take the opposite stance: don’t do what you read below!

Instead, reflect on the fact that people, perhaps including yourself, have engaged in the acts I am about to describe. These faux pas apply to both sexes. In the game of dating, we are all at risk of being that guy (or girl). Also, note that I’ve exaggerated some of this poor advice for the sake of making it more obvious. But again, don’t do it!

On occasion I will say just a few words about how to approach the dinner date experience so that you actually increase your chances of having a good time. I will highlight these affirmative suggestions by placing them in capital letters and italics so that you can tell them from the disastrous behaviors that make up most of this essay.

YOUR PRE-DATE GAME PLAN:

1. As a first step in destroying your confidence, consider that this woman does not really know who you are. Now, I don’t mean this in the sense that she has very little knowledge of your inner workings and life history. Rather, I’m referring to the chance of mistaken identity. She likely envisions a tall, handsome, witty character with whom she shared martinis, moonlight, and flirtatious banter (or was that the guy named Steve?). Regardless, once you arrive at her door, she is likely to realize two very important things: she is sober and you are not Steve.

2. Continue to ponder the possibility that your muse imbibed too many Cosmopolitans during your initial encounter a few days ago. Now reflect on the fact that your friends have often told you, “Dude, you’re way funnier when you are drinking.” You can now reasonably conclude that your date either does not know who you are or she does, but you looked and sounded a lot better when you both were intoxicated.

3. Having ruminated about the first two items for several hours (to the point of a ruinous case of pre-date jitters), jot down a list of every bad date you’ve ever had. Think back to all the humiliations, all the rejections, and especially the time that you got nauseous at Chili’s. Now extend your attention to your miniscule place in the universe, thereby further reducing your confidence.

4. Remember that one of the potential problems in meeting anyone new is that you can run out of things to say. Knowing this, write down a list of potential conversation topics. Then open your window and scream “Adios blow-up doll! No more inflatable girls for me. I have a date with a real live woman!” Make sure that you are loud enough so your neighbors can hear you.

5. Recalling that your date said on the phone that she loves Thai food, choose a dinner destination based solely on your own palate. Your reasoning? Women don’t eat in front of guys on first dates, right?

6. Remember that appearance is key to a successful first date. At the same time, however, consider that paying too much attention to grooming could be seen as a weakness. The solution to this dilemma? Rely on the words your incarcerated father once told you, that there is nothing to fear when you drench your body for 30 seconds with Axe Body Spray.

  • REAL ADVICE: DON’T DEFEAT YOURSELF BEFORE YOU GET STARTED. TRY TO REMEMBER WHY YOU WANT TO GO OUT WITH THIS PERSON AND REALIZE THAT SHE IS ALMOST CERTAINLY LOOKING FORWARD TO GETTING TO KNOW YOU AND HAVING A GOOD TIME. YOU CAN DRIVE YOURSELF CRAZY WITH ANTICIPATION AND PREPARATION. DO TRY TO LOOK YOUR BEST, BUT, IN THE END, YOU ARE WHO YOU ARE. IF YOUR DATE IS COMPATIBLE WITH YOU, SHE IS NOT EXPECTING THAT SHE IS ABOUT TO GO OUT WITH THE FIRST FLAWLESS PERSON IN HISTORY.

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THE DATE ITSELF:

7. If you are prone to hugging “hello,” go ahead. But remember — you want to make an impression. Therefore you must squeeze your date’s bottom a minimum of three times in quick succession during the embrace. Why three? Because you don’t want her (or him) to think that the first two squeezes were an accident. This will definitely get noticed. If you are a man, it will tell your companion that you are a rude, overconfident caveman. If you are a woman, it will inform your new acquaintance that you are in heat.

  • REAL ADVICE: WHATEVER YOU DO, DON’T DO ANY BOTTOM SQUEEZING OF THIS NEW PERSON, UNLESS YOU WANT HER TO CALL THE POLICE OR KICK YOU IN THE GROIN!

8. Upon arriving at the restaurant, realize that you left your list of conversation topics at home and that you have no recollection of what it included. If you are a drug abuser, this is the perfect time to go to the restaurant men’s room and snort a quick line of coke.

9. When you return from the W/C, begin to focus on your facial expression and body language. Your internal monologue should sound something like:

a. “Am I moving my hands too much?”
b. “Did I just scowl?”
c. “Is my eyelid twitching?”
d. “Did I leave some coke on my face?”

  • REAL ADVICE: IF YOU CONCENTRATE ENOUGH ON WHAT YOU ARE SAYING AND DOING, HOW YOU LOOK, AND EVERY CONCEIVABLE INADVERTENT LAPSE FROM SOME IMAGINARY STANDARD OF BEHAVIORAL PERFECTION, YOU WILL BE UNABLE TO ACCOMPLISH WHAT YOU SHOULD BE DOING: ENJOYING THE COMPANY OF A POTENTIALLY INTERESTING AND LOVELY PERSON WHO WANTS TO GET TO KNOW YOU.

10. Back to what you shouldn’t do: be very conscious of the possibility that you may become uncontrollably aroused by the feminine charms of your companion, to the point of levitating the rather low table at which you are seated, thus drawing the attention of everyone in the restaurant. Should this happen, do one of the following:

a. Make no eye contact at all with your companion.
b. Keep your eyes laser-focused on the woman until she asks you if you have a staring problem.
c. Look at and speak to her cleavage, not her.

11. Sprinkle the conversation with the “F” word. You know, “this” and “F that;” “F him” and “F her.” Use the words “whore” and “bitch” enough to give your companion a good sense of your opinion of women. Belch whenever possible. Sneeze on to the femme fatale’s food. Take things off her plate without asking.

12. Your dating disaster will only be complete if you offer Ms. Right some illegal drugs. Carry a full array of products in your brief case. She will consider the offer enormously thoughtful of you.

13. From the beginning to the end of the night tell your heart-throb that she is beautiful, gorgeous, stunning, etc. Ignore her when she implores you to stop. Keep doing it until she begins to scream the “F” word you taught her in step #11.

  • REAL ADVICE: DO GIVE A SMALL NUMBER OF COMPLIMENTS, BUT BE SENSITIVE TO WHETHER YOUR DATE IS COMFORTABLE WITH THIS. WHATEVER YOU DO, DON’T GO OVERBOARD. WITH EVERY ADDITIONAL COMPLIMENT, YOU RISK MAKING YOURSELF SEEM EITHER INSINCERE OR TOO ENAMORED OF YOUR COMPANION TOO SOON IN THE RELATIONSHIP. ALLOW THERE TO BE SOME MYSTERY AS TO YOUR FEELINGS, NOT SLAVE-LIKE DEVOTION FROM THE START OF THINGS.

14. Talk politics or religion from an early point in your dinner. Take impossibly extreme positions, always being careful to communicate that anyone who doesn’t agree with you is an idiot. Pick a fight if you can.

15. Do not let your new friend speak. Interrupt her whenever possible. Dominate the discussion. Talk only about yourself. Ask her no questions about herself and show no interest when she does manage to say something. Discuss past girlfriends and how lucky they were to have you in their lives. Praise yourself and your wisdom ad nauseam.

Alternatively, put yourself down at every opportunity. Look to this woman for reassurance. Lapse into a fetal position. Display as much self-doubt as you can. Tell her in great detail about your lifetime of therapy. Make it clear that unless she is falling in love with you, your life will be forever meaningless.

  • REAL ADVICE: NEW RELATIONSHIPS GENERALLY WORK BEST WITH A GRADUAL APPROACH TO SHARING INSECURITIES AND VERY PERSONAL INFORMATION. A FIRST DATE IS NOT THE SAME THING AS WRITING A MEMOIR OR ENTERING THE CATHOLIC CHURCH’S CONFESSIONAL BOOTH AND ASKING FORGIVENESS FOR ALL YOUR SINS. DO TAKE YOUR TIME IN GETTING TO KNOW THIS NEW PERSON.

16. See how many other hot women you can flirt with in the course of the evening. If your date fails to notice, be sure to point out the babes and mention the physical attributes that appeal to you.

17. Keep your cell phone on the dinner table and check it frequently. Text while you talk. Use the phrase “Did you say something?” as often as possible.

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18. When the bill comes, say that you forgot to put enough money in your wallet, but “I will totally make it up to you during the porn flick I picked for later in the evening at my apartment.”

19. At the end of the night, despite numerous signs that your female friend can’t wait to be away from you (including her mentioning that she is going to move to Paraguay tomorrow), make every effort to be a stud. Specifically, try for a good night kiss that would make a plumber proud; or, if you prefer, a surgeon who wants to get deep enough inside her mouth to perform a tonsillectomy.

POST DATE WRAP-UP:

Congratulations! You have not only guaranteed your own loneliness, but managed to give your date a case of Post Traumatic Stress Disorder. Once she recovers she will tell others about you. With any luck, most of the female population of your community will be on the alert, having seen your photo on Facebook. It is only a matter of time before small children will point at you in the street, laughing so uncontrollably that they begin to burp up their lunch.

  • REAL ADVICE: OK, THE DISASTER DESCRIBED IN THIS POST IS A GROSS EXAGGERATION. BUT, KNOWING WHAT NOT TO DO CAN HELP YOU AVOID CREATING A REGRETTABLE EVENING FOR YOURSELF AND YOUR FUTURE LADY FRIEND.
  • MORE REAL ADVICE: ON THE OFF-CHANCE THAT YOUR CONFIDENCE HAS NOT BEEN FULLY DESTROYED BY DATING EXPERIENCES ANYTHING LIKE THIS, THERE ARE SEVERAL STEPS YOU CAN TAKE: SEARCH YOUR PERSONALITY AND BEHAVIOR FOR POSSIBLE SIGNS OF OVERCONFIDENCE, INSINCERITY, OR INSECURITY. VOW TO CHANGE. ASK FRIENDS (AND EVEN WOMEN YOU’VE DATED) WHAT TURNED THEM OFF. FIND A GOOD THERAPIST. ALL THIS TAKES INCREDIBLE COURAGE AND EFFORT, BUT CAN BE VERY INFORMATIVE. AS I HOPE YOU’VE LEARNED, RUINING A DATE CAN TAKE JUST AS MUCH ENERGY.
  • ONE LAST BIT OF REAL ADVICE: DON’T MAKE A DINNER DATE A MATTER OF LIFE OR DEATH. IF YOU DO, YOU WILL DIE A LOT!

This essay comes from Chapter 24 of the forthcoming Encyclopedia of Ruining Your Life.

The top image is a Joker by David Bellot. It is followed by a Goofy Smirk by Bruce from San Francisco. The final painting is entitled The Desperate Man by Gustav Courbet, dating from 1843. All are sourced from Wikimedia Commons.

2 thoughts on “How To Mess Up a Dinner Date: A Beginner’s Guide to Dating Misery

  1. I don’t date. As a writer and member of a writer’s group, whenever I accept an invitation from a fellow male writer for coffee or dinner, I see it as an opportunity in building friendship.

    During my last dinner-meet, as I perceived it, the conversation headed in a direction that left me extremely uncomfortable. It became clear that a simple writer-writer friendship was not in our future.

    There will be no second chance.

    Like

  2. There is certainly no oversupply of good men, so it is hard to argue with your decision.

    Like

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