7 Awkward Dating Situations and How to Deal With Them

Dating fails

So, you’ve done the hard part, you’ve arranged the date. Now you should rest easy, right? Wrong. There are so many awkward situations and dating fails that can happen on a date and they may not be so easy to smooth over when facing a complete stranger. If you find yourself in an awkward position – don’t freak out! It takes confidence and experience to brush over life’s little embarrassing discrepancies.

1. Covering yourself in food

You’re a messy eater. It might be endearing to some, but not on a first date. Do yourself a favour and take a look at the menu from an educated perspective. You know yourself better than anyone else so eliminate all of the messy food that you think may be a risk (pasta, noodles – things like that). Take your time when eating and remember the manners your mamma taught you, no one wants food spray all over them. Let’s keep it classy people!

2. No conversation

The conversation may not be flowing, you might want to make a sneaky exit under the table and out through the kitchen window, but don’t be disheartened. Try to find something you both have in common. In some situations, anything will do. It’s good to ask questions and observe, but don’t be a dull Deborah. If my sparkling advice has not saved your date and it starts to feel like a chore, it’s time to call a cab.

3. Mention of exes

Just don’t do it, it’s as simple as that. You may have a funny story to tell, but mentioning an ex, despite how “over it” you are, is awkward and seems like you’re still hung up on them. Your hilarious memories can wait until you’ve developed more of a bond, and even then, some people don’t like any mention of exes whatsoever. I’ll let you into a little secret: if I mention a story with an ex, I refer to them as a “friend” in the story. Cheeky, right?

4. Wardrobe malfunction

You may have spilt red wine on a white dress, you may have noticed your fly has been undone for the whole night – keep calm and hope your date hasn’t noticed. If this has ever happened to you, you will know that this is one of the most humiliating things that can happen in your adult life (or at least it seems so at the time). Be subtle when you excuse yourself to the bathroom and see if you can fix it with the contents of your handbag or pockets. If you can’t, you will have to make a judgment call between making an excuse to leave, trying to hide it or point it out and hope for the best.

Another fashion faux pas may involve arriving at the meet point too dressed up or down for the venue. In this situation remember -confidence is key, you might stick out like a sore thumb, but why let that ruin your night?

5. Paying the bill

Everyone has different thoughts on the matter, but let’s face it, whether you’re a feminist or not you should both offer to pay your share. The debate began when asking some friends at work, and the answer varied depending on gender mainly. Most women said they would offer to go halves but ultimately would still expect their date to pay. Another factor to take into consideration is who invited who out? We now live in the 21st century, when a woman is more than capable of paying the bill or at least her fair share, but this can be seen as emasculating to proud men. I have heard an abundance of cringe bill splitting stories – my advice would be to not expect anything, and if you can’t afford it you shouldn’t be going out in the first place.

6. Morning breath

Things may have progressed to an over-night rendezvous and you don’t have your toothbrush (or you do have it, but it’s all the way in the bathroom). Suck it up and act normal, chances are your other half is probably feeling the same way! Unless your breath has a stench of a Portaloo after a festival, most people won’t mind. Besides, trying to hide it with your hand for example will only draw more attention.

7. First time using the toilet

Ventilate, ventilate, ventilate. This should really be thought of as a victory as you have now entered a stage of comfortability that a lot of people feel shy about. Think of it this way, everybody has to use the bathroom, so regardless of where you are, nature will take its course. To be honest, you are basically living together after this stage and I think it’s adorable.

Things are really getting serious if you fart in front of each other, particularly with no humility. If you manage to reach this stage of a relationship, you are no longer dating and are in fact past the honeymoon stage. Congratulations! This means that all of your miniature awkward moments have contributed to a healthy relationship that can appreciate the odd trip on a step.

I know it’s easier said than done, but in any embarrassing situation (and not just romantic ones) you want to try to brush it off.  You’re out to have a good time, don’t dwell on the silly little details and focus on the bigger picture, like do you fancy them or not?! Think of these little hiccups as a test of chemistry; and unless your partner has no tact whatsoever, it should be forgotten about very quickly. Major brownie points if you can laugh it off together – maybe one day you might be laughing about your dating fails at your wedding. But don’t say that to your date, that’s embarrassing.

Charlie is a graduate in Media and English Literature, an excitable blogger and closet comedian. Also, Netflix enthusiast, friend to dogs, foodie, book club aficionado and wannabe jetsetter. Follow her on Twitter and check out her blog Miss Moore.


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