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10 Most Awkward Things That Could Happen on a First Date

A fact that I’ve slowly come to embrace is that I’m kind of clumsy. So you can imagine over the years that I’ve learned how to gage how awkward things could ever get. This personal list consists of the worst-case scenarios that could happen on a first date. Disclaimer: some of these may or may not have already happened to me.

1. Your friends So when you’re like 13 you think no one could possibly embarrass you more than your parents. WRONG-O! One of my most painfully awkward moments on a first date happened when two of my best friends “inconspicuously” started following us. Yes, they followed us. My friends spotted me meeting my date in front of my building and decided it would be a great opportunity to see who I was going out with. They ran to catch up with us and walked very closely behind us and giggled. It was so painfully awkward that I just came clean and admitted to it. To this day, I’m still plotting my revenge on them.

2. Your phone Although I’ll admit having text “previews” on your iPhone is very convenient it is also a recipe for disaster. My friends and I have no filter, at all. So it only takes one text to completely embarrass you in front of your date. So here’s how I imagine this awkward situation going down: you’re showing him a picture of your adorable dog when a text from your roommate comes saying “HAY HOW IS UR DATE GOING? HUH? HUH?” Not only does it sound like your friend is crazy (which she is) but it also sounds like you’ve been telling everyone and their mother about your date. Which would freak anyone out.

3. Your shoes One thing I always think about when I put on heels is “what if I trip?” I remember going out to dinner with my family one night and thinking I looked like the hottest thing on earth with my huge heels. I had my nose so high in the air that I failed to look at the ground, I tripped and absolutely ATE IT in the middle of this super fancy restaurant. I completely ripped my jeans on the knees. What if this were a date? HOW COULD YOU EVER RECOVER FROM THAT? Wear comfortable shoes ladies. 

4. The unsolicited relationship talk Let’s say you both try to take the T to your first date destination. This is a nice choice, it gives you both some time to talk and it’s economically friendly. Nothing could go wrong, right? NOPE! That cute old lady your date just gave his seat up for could be the beginning of your awkward date. She could pop that question: “You two are so cute, are you boyfriend and girlfriend?” And at this point you’re both thinking “HEY LADY! Boyfriend and girlfriend? Puh-lease! We hardly know each other.” But where do you go from there? The date feels like it’s been absolutely tarnished.

5. Your big mouth If you’re anything like me, you can be slightly opinionated. That could lead you to say something that may or may not offend him. And it could be anything from “I think white cars look like refrigerators on wheels” to “Running is such an un-manly sport” to offend him. So try to keep those irrelevant pet peeves to yourself. At least for the first date.

6. Your big mouth part two There’s nothing that makes for 10 seconds of awkwardness like a burp. So maybe don’t order the sparkling water.

7. Your big mouth part three For the love of Pete, do not order something off of the menu infused with raw garlic and onions. Do you want to put on “Man Repellant?” Not only will you be paranoid about bad breath, but also he may or may not have to suffer your newly acquired scent.


8.  Your bladder It’s half an hour into your date and you start to ask yourself why you ordered three iced teas. They are finally catching up with you and you know if you give into your bladder, you’re probably going to have to get up to go to the bathroom five times. How on earth are you going to explain going to the bathroom five times? Are you supposed to say something? Do you acknowledge the fact that you consumed three iced teas or the fact you have a tiny bladder? These are questions I don’t really know the answer to. So I just order water because there is only one allotment for bathroom usage.

9. Your hello Coming from Miami (where you give everyone a kiss on the cheek to say hi), I’m never really sure what the protocol is when it comes to greetings. Do you handshake? Do you wave? Do you hug? High-five, perhaps? I never really know. You haven’t felt uncomfortable until you go in for a hug when someone goes in for a handshake. My advice, just wait until they start saying hi to determine which form of greeting is appropriate. 

10. Your liver Although everyone loves their sangria. Don’t be a “sangria stage-five clinger.” So it tastes just like juice buuuuut, when you stumble out of your chair because you are too drunk to function that may be a deal breaker.

The bottom line is, awkward things happen. It’s a first date, sometimes things go wrong. But there’s nothing funnier than going home to your best friends and laughing about it. Or even better, if your date likes you because of your awkwardness. Who knows? Maybe you’ll hit it off and the two of you will laugh about these moments for years to come. We can’t always control the things we do, I mean there are some tricks of the trade here and there, but for the most part be who you are. Anyone you like should like you because you’re you!  


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