How to Handle 10 Awkward Date Moments

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Nobody ever wants to encounter an awkward situation while out on a date.  Imagine running into your ex while out with your new boyfriend.  Or, you lean in for the goodnight kiss and notice your breath stinks of garlic. 

Perhaps you knock over your date’s glass of red wine all over his pants.  Whatever the case, these things happen, and it’s not so much the event itself that spoils the date, but your reaction to it.  How should you compose yourself during an awkward situation on a date?  

Here is some advice on how to handle 10 different dating disasters.    

  1. You’re a traditional guy and a modern woman asks you out: In today’s world, this is perfectly acceptable. 20 years ago or so this might have turned a few heads, but in 2020 women can and should ask men for a date.  
  2. Who pays the bill?  The server places the bill on the table and there’s silence and you both look at each other.  Don’t let this happen.  As a sophisticated host, arrive early and provide a credit card, or call the restaurant in advance. Women in male-dominated cultures must do so if they extend the invitation.
  3. You refer to your date by the name of your ex: Imagine being out on a date and you accidentally refer to your date by the name of your ex.  There’s only one thing to do besides hope they don’t walk out on you: apologize profusely and don’t ever do it again. 
  4. Laugh at those things you can’t control: Maybe you spilled your soup all over your nice Polo shirt.  Maybe you walked into a glass door.  Perhaps the comedian at the show pulled you on to the stage and had a little fun with you.  Don’t let these awkward situations get the best of you. Your demeanor and how you handle it tells your date a lot about you. 
  5. Be careful with alcohol: A glass of wine or cocktail with dinner is perfectly acceptable; however, don’t drink to the point of no return.  Alcohol might calm those date night jitters, but if you have to call for a cab or start dancing on the tables, you’re not going to impress your date.  
  6. You momentarily forget your manners: It happens.  You’re out on a date and you burp, shove the food in your mouth, chew with your mouth open or put too much water in your mouth and it flies out and lands on your date.  Catch the mistake and apologize before your date says something.  When you own up and take responsibility, it speaks volumes about the kind of person you really are.   
  7. Awkward conversations: Don’t ask your date how many kids they want to have or how much money they make.  Stay away from talk about sex, politics and religion.  Stick to lighter topics likes books, food, movies, hobbies and sports.  Ask questions that help you get to know your date better.  
  8. You run into someone of meaning: Maybe it’s your boss, your parents or girlfriends. You’re caught off guard.  How do you handle the situation?  Keep it short and make an introduction.  “Hi, NAME.  Please meet Mike, my date for the evening.  We have to catch the 9:00 movie. Talk to you soon.”
  9. You run into your ex: This is one of the most awkward situations possible, but you can handle it like a pro.  You have two choices: 1. Hope they don’t notice you and say nothing at all.  2. You cross paths.  Although it’s awkward, there’s a lot riding on this moment as your date will see what you’re really made of.  Be polite and courteous no matter what you think of the person.  Say hello.  Ask how they are doing.  Introduce your date.  Close it out by saying, “It was nice to see you.  We really must be going.  Have a good evening.” 
  10. You are absolutely miserable on this date: Although you might not necessarily care for your date or be having the time of your life, it’s a few hours at most so try to make the best of it.  Refrain from pulling out your Smartphone and texting your friends or surfing the web.  If all else fails and the date has no end in sight, simply say something like, “I apologize.  I do need to get going soon as I have a big presentation at work tomorrow morning.”

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