Top 5 Awkward Dating Moments and How To Overcome Them

Ever been on a date that just went all wrong? For one reason or another things started rolling downhill. So what do you do? Throw in the towel and walk away? Or, can you redeem yourself? What if you’re on the receiving end of the awkward situation? Do you stick around or is it a red flag? So much to think about, huh? Dating isn’t easy, but it is fun … and the only solution is to not take yourself too seriously. Easier said than done, right? Well, not too long ago I got a question about bouncing back from a bad date, and the advice that I gave was that it is possible.  All it takes is to lighten up the awkwardness or even just let it slide.

Top 5 Awkward Dating Moments and How To Overcome Them

Awkward-Dating1. Bodily Functions Gone Wrong

Ok, this is embarrassing. What is? Well, let me see … Ever farted by accident (or not so accident but didn’t think it would be noticed)? Ever got sick to your stomach on a date and ended up running to the restroom several times a night? What about you were so nervous that you sweat profusely? Has your date been so hot that you couldn’t help but, um, stand on attention? Did you get your period and didn’t notice? Burping? Snots? Well, we’ve certainly all been there! Both on the receiving end and on the doing end. So what do you do with that awkward dating moment?

Well, best thing to do is try and avoid it by not going on a date if you’re having gastro-intestinal problems. Also, be careful not to eat or drink something that might make you sick. Proper hygiene practices also help, if you know you have weaknesses then take care of it before the date. If you’re on the receiving end, then try and be merciful because typically it’s an accident and they are mortified that it happened. If it’s not an accident, like burping and farting on the date, well, then, that’s a red flag. You decide if that’s something you can tolerate.

2. Spilling Food or Drink

Sometimes we accidentally spill food or drink on ourselves, or, God forbid, on our date! Yikes! Imagine!? It happens. No big deal, but, completely embarrassing. I mean you didn’t do it on purpose, but could you have avoided it? Yes, probably. How? Well, make smart food choices that aren’t messy and difficult to eat. You also don’t want to over drink which might lead you to do things that embarrass you. If you spill on yourself then clean it and laugh about it, people like someone who can laugh at themselves. If you spill on your date just apologize and help them clean it up. The whole point is not to make a big deal about it. This awkward dating moment needn’t be that awkward.

3. To Kiss or Not To Kiss

Great dates always end in a kiss, right? Well … not always. What happens when you go in for the kill and they move away? You respect their wishes, that’s what. If you awkwardly go in for the kiss and they pull away or turn their cheek don’t take it so hard, they might not be ready for it, or they think it’s too early for that sort of thing. Just make sure to respect their boundaries and pay attention to the cues they send you. Usually, you will know whether or not to try. Don’t be ruled by lust and a kiss, especially a first kiss, needs to be sweet and not porno. This awkward dating moment can actually be turned around, just approach the whole kissing thing respectfully and not aggressively and all will go well.

4. Running Into An Ex

This has happened to me before, it was definitely awkward! Do you say hi? Do you not? Your date will definitely see your reaction and want to know why. You don’t want them to think you still like your ex so you want to be discreet and let it roll off your shoulder. The important thing is not to react. Leave your past in your past and focus on your present. Your date should be all you’re thinking about. If your ex comes over to say hi then say hi, introduce them to your date as an old friend or whatever and keep it short. If your date’s ex makes an appearance then don’t make a big deal out of it and don’t make it more awkward than it has to be. This awkward dating moment is inevitable, so don’t give it more attention than it needs.

5. Your Date Doesn’t Look Like Their Picture

This is a reality of the online dating world. People make inaccurate representations of themselves. They put pictures of themselves that don’t accurately show what they currently look like. How many times have you met up on a date and your date looked much older or larger or whatever? I know it’s happened to me, one guy put a completely different picture of himself. I’ve been on several dates where the guy actually made a point to say that he was happy I actually looked like my picture. Have we really stooped THAT low? What do people expect? That their personality will win the person over even if they misrepresented themselves? More of than not, it means the end of that date and no second date. So if you’re on a date and they don’t look like their picture or they’ve misrepresented themselves, then see it as a red flag and choose whether or not you’re willing to look past it. If not, then this awkward dating moment is a walk away moment. If they start with a lie, then bigger deceptions are most likely in the cards as well.

awkwardThese are just a few of the most common awkward dating moments and how to overcome them. Make sure that you take everything that comes lightly and don’t take yourself too seriously. Awkward moments happen, just go with the flow and learn to laugh at yourself, it will not only make you feel better, it will make your date feel better as well. What do they say? “Don’t sweat the small stuff because it’s all small stuff”!



Readers: Have you ever had any awkward dating moments? How did you overcome them?

Your Sister in Dating Bliss,

Single Dating Diva

Copyright Single Dating Diva


  1. I actually went on a date and was feeling a little nauseas but decided to go anyway. After some pizza the nausea came on stronger, but We were having a great conversation, and when I told him I wasn’t feeling well he suggested we take a walk in the park nearby. While walking he took advantage of the romantic moment and went to kiss me. It happened to be in the exact moment I had to barf…literally kiss then me running to the tree to throw up. Of course I was utterly humiliated but he was super cool about it. Despite the pretty bad ending to a first date we ended up dating for 2 years and laughed about it a lot later on. Silly things like that aren’t worth losing someone great over! Great post and excellent advice.


    • Thanks for sharing your story Meena! It’s a perfect example of how an embarrassing moment doesn’t have to be the end of the world. If both of you can move past it, then it will be something to definitely laugh at later.


  2. aaah, to kiss or not to kiss. that is the question. I HATE that awkward end of the night moment (or I did before I was married). Usually I just never kissed them until after the third date. That way I knew for SURE it wasn’t too soon. That way I didn’t have to worry about if they didn’t like me (if they didn’t like me they wouldn’t go out with me a third time). And if they wanted a kiss on the first date it made them wait. Looking back, I guess I was a bit of a kissing snob.


    • Thanks Aaron! Everyone has to do things at their own pace … sometimes you’re in the moment and you just “feel it” other times it’s a bit more awkward. Important thing is to be respectful … and NOT be a kssing snob! LOL!


  3. I’ve actually dripped ice cream on myself on a date and gone on dates with guys who turn out to look nothing like their profile pictures. Some mishaps are understandable because they are mistakes (usually), but the profile picture thing is just an outright lie and intolerable in my book.


    • Thanks BSG! Some awkward moments are totally accidents and we should be more forgiving of them, but if something is intentional then I’m definitely not so forgiving either.


    • Thanks Melany! Those are terrible ones because you don’t even know you have them! I am one of those people, though, who actually tell people when they’ve got food in their teeth or a bat in the cave or their fly is low … you know, because I’m nice like that HAHA


  4. #5 is probably the worst! You always want them to look like their photo (unless they look better which is rare). I can’t think of too many awkward things that I did on the first date, but I did have a date get a little popcorn piece stuck in her teeth and got super-humiliated when I told her. I didn’t want it to just stay there and she appreciated that, but was still blushing uncontrollably.


    • Thanks Q! Honestly, I’d rather someone tell me if I have something stuck in my teeth or anything where it isn’t supposed to be. Maybe it’s a bit embarrassing but imagine how distracting it is for the other person if you’ve got food in your teeth, that’s all they will be able to focus on hahaha


  5. The kissing question can be a hard one to navigate. There’s a fine line between a man who takes action into his own hands– sexy– and a man who doesn’t read any of your signals– or if you’re trying to get him to read a signal and he’s refusing to pick up on it. I guess if it were easy to figure out, we’d all be coupled up! Thanks for the great post!


Comments are closed.