The SW Experts | 8 Awkward Dating Moments and How to Get Over Them Quickly
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awkward dating moments

8 Awkward Dating Moments and How to Get Over Them Quickly

awkward dating moments
1. You Wear your Favorite Heels on your First Date

Have you ever had that awkward dating moment on your first date, when you walked up to your date and just realized that you’re somehow towering over them. What happened? You’ve decided to wear your favorite heels, the ones every gal pal of yours is raving about.

You did check your date’s height, you vaguely recall the two of you being of similar height, but once you opened the wardrobe, all previous thoughts flew out the window.

We love heels we hate heels, but we can’t resist heels. Carrie Bradshaw, we blame you.

You notice his confused look. You’re just about to say hello and exchange pecks on the cheek and it feels awkward. Get over the moment, by stepping out of one shoe, which will restore your height, do the pecks and put the shoe back on. If he’s got a good sense of humor he’ll appreciate it. Better yet, it might even become a funny conversation starter like”Hey, do you always take your shoes off when you meet your date?” However, if you’ve got boots, it’s another story. Bring your boots to the party. Mention the fact that they might be high heeled, but they’re your favorites and you hope he doesn’t mind you strutting in them. It could make him feel special.

2. The Meeting Place is a Venue That is Closed.

You’ve arrived at the venue. The door is looked, the windows are dark, you peer in to see an abandoned space and wonder if it’s a bad joke. Especially since your date apparently lives just around the corner. You might feel awkward standing there shifting your weight from one leg to the other. Don’t. Venues appear and disappear in a flash if business goes down. Call him or text him straight away and agree on a new meeting spot or just meet there and walk somewhere together.

3. He Doesn’t Look Like His Profile Photo

awkward dating momentsYou’ve arrived a touch early to the pub and it’s a cold November evening. You decide to go in and have a drink. There are a few people around the bar, some men on their own. Also there is a new one coming through the door every 2 minutes. You’re trying to figure out which one is him, based on his profile photo. Is it him, the one with the green jacket? Or him, with the piercing blue eyes? Surely, it’s the one with dark brown hair. You decide to call him, to see who’s phone rings. Nobody’s in the room. However the next man through the door is holding the phone to his ear, looks at you and starts walking in your direction. Could that be him? The resemblance is minimal. After the initial greet, you blurt out that he doesn’t much look like his photo. Of course not, he’s grown a short beard. He gets into the defensive and returns the favor. You don’t look like your photo either. “Really?” you say. “Maybe because my hair is now curly.”But what you think is, ouch, do you look worse? He must be thinking the same. Awkward. The best is to laugh it off. Joke about it, since we’re not talking about being 20 pounds or 20 years different (and we know that happens a lot too). Just ask “Does your twin brother always send you on his dates?” And for good measure, add “My twin sister does that all the time.” Even if he believes you for a split second, you’re bound to get a smile in the end.

4.You Want To Meet For Coffee, He Wants a Drink

I don’t know how it is with you, but I find waiting for a guy in a bar rather awkward. I much prefer a coffee shop for that matter. Why wait? Well you give yourself time while travelling. You don’t want to be late. Chances are you get there first. Ogling strangers by yourself in a bar is just not fun, is it? He doesn’t do coffee. Awkward. Get over the moment quickly, by suggesting that he can meet you in the coffee shop and you can both walk over to a nearby pub or bar. Job done.

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5.The Awkward Dating Moment When You Share Too Much

We have a work CV, a bio and more recently an online dating CV. Everybody wants to know about how did you end up on a dating site, how long you’ve been there and what’s your experience of it. As if it were a weird experiment. Which it is, no doubt, but it’s a sign of the times. Thus, embrace it and go with it.

If you kept your dating dairy details at a bare minimum and you find that he’s talking about the ex wife’s mental illness, or her cheating ways, or about sex positions with his longest fling, it’s awkward. Get over the moment, by writing him off as someone not ready to date yet. And suddenly you can relax as you don’t have to work on your date impressions any longer. Cut the evening short before too many drinks, unless you fancy the pants off him, despite his blabber. It’s been known to happen.

6. Mid Date You Realize You Want Different Things

He wrote to you about his hectic lifestyle, his travels and about the fact that he’s looking for a relationship. You meet, he buys the drinks. They’re followed by dinner. He doesn’t talk much. So, you talk to fill the silence. And as the drinks pile up you try, and in your opinion, manage fairly well to be ever so funny. And then it dawns on you. He’s not here for you to get to know him. He just wants a lay. Awkward.

Regroup. The bill arrives. You offer to chip in. He refuses, but your message is clear. You’re not the entertainer for the night any longer. You buy him a night cap and you put it in words as well. Gently. Just so there are no misunderstandings.

7. He Won’t Take His Eyes Off You

You liked his photo. He has deep blue eyes. The trouble is that he doesn’t take his eyes off you for a second. For him, connection is paramount. And you can only blame yourself, since the moment you met, you locked lips passionately. That’s what weeks of emailing can do to some.

It can build up expectations to a mighty high.

Do you feel the connection you felt when emailing? Erm, not really. Awkward. Get over it quickly, by suggesting to go to a gallery or a movie. There you can both stare at something else. Or excuse yourself and cut the date short. Pre booked phone calls with friends who check on you aren’t a bad idea after all.

8. He’s at the Same Dating Event After He Shunned You

You’ve gone out once and he never called. And there he is, at the same speed dating event you’ve signed up for. Awkward. You can confront him. You can pretend you’ve never met. Or you can just get over the moment quickly by acknowledging that the world is a small place and character is a precious commodity. Just the same, if you’ve left someone hanging without telling them where they stand, be prepared to bump into them any time anywhere, or better yet, pick up that phone.

And here is and awkward dating moment we yet have to find a way to get over quickly: He suddenly approaches and kisses you and you press your lips together in defense. Awkward.

Words can mask feelings, but body language is much more telling. What would a quick way of getting over the moment be? The challenge is yours. Tell us your take.


My Dating Photos