How to Handle 10 Awkward Valentine’s Day Dilemmas

by Bebe Brown on February 13, 2019 in Lifestyle,
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Dating is challenging enough these days, and getting things right on Valentine’s Day is even more important. But what happens when things don’t exactly go according to plan and you find yourself in a really awkward situation?

Don’t panic! Help is at hand from Austin-based Sharon Schweitzer, an international etiquette and modern manners expert, and founder of Access to Culture. She offers this advice for some of those potentially uncomfortable situations.

1. You’re a traditional guy and a modern woman asks you out for Valentine’s Day

In today’s world, this is perfectly acceptable. 20 years ago this might have turned a few heads, but in 2019 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.


If you run into your ex while you are on a Valentine date night, be polite and courteous no matter what you think of the person. Photo James Discombe/Unsplash

3. 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.”

4. Your date has spinach in their teeth

You’re eating dinner and notice that your date has a big piece of leafy green spinach stuck between her teeth. Do you say something or let it go? It’s best to nicely say something because if they see the spinach in the bathroom mirror, for example, they will be embarrassed at first, and then upset that you didn’t tell them. Say something like, “This food is so good but the spinach keeps getting stuck between my teeth. Oh, by the way, there’s a very small piece sitting right there between your teeth. You have beautiful teeth by the way. How do you get them so white?” 

Spinach in their teeth? Better to tell! Photo Hian Oliveira/Unsplash

5. 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. 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.

6. Laugh at those things you can’t control

Maybe you spilled your soup all over your nice 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.

7. Awkward conversations

Don’t ask your Valentine’s 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.

Be careful with alcohol when you are with your Valentine. Photo Justin Aikin/Unsplash

8. 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 an Uber or start dancing on the tables, you’re not going to impress your date.

9. You are absolutely miserable on this date

Although you might not necessarily care for your date or you’re not 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 phone 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.”

10. Good breath equals good kiss

If you decide to go in for the goodnight kiss, make sure you have a breath mint handy to erase the memory of the garlic bread you ate with dinner.

Cover photo Sharon McCutcheon on Unsplash