30 Embarrassing Dating Fails You Need To Experience Before You're 30

by Zara Barrie

My 20s aren't defined by cool jobs I had, how fast my metabolism was or how deeply I fell in love. My 20s are defined by my dating fails, babe.

When I 23, I vomited on a first date.

I blew chunks of barbecue chicken all over the sidewalk, and I was drenched in sweat, body trembling and wildly gagging as my date stood nervously to beside me, unsure of what to say.

When I was 25, I was really into wearing these over-the-top, sky-high, chunky heels.

Seconds before a date with a very chic fashion executive, I tripped over a crack in the pavement and the heel of my shoe snapped off. My date then found me hobbling on the pavement, broken heel in hand, stress-induced cigarette hanging out of my mouth and a look of terror across my face.

She was wearing Balenciaga motorcycle boots and pressed-velvet smoking jacket.

"Zara?" she asked as she took in the site of a crackhead-looking version of me. I stumbled into a deli, hid behind the canned foods and prayed to a God I didn't believe in to please let me disappear into the air.

When I was 27, I was finally getting it on with a girl I had lusted after for seven years.

I totally forgot I was on my period and bled all over the bedsheets.

Caught up in the blissful feeling of her body on top of my body, I totally forgot I was on my period and bled all over the bedsheets. It wasn't delicate, first-day bleeding either. It was alarmingly bright-red, third-day bleeding. It looked like a Hollywood crime scene.

These are just three examples of my embarrassing dating fails in my 20s.

And as traumatic as they were, I'm wildly grateful for the love mishaps of my youth.

Why? Well, they made for excellent content for my pending memoir, they taught me you can't die from embarrassment and, most of all, I learned the cool people who are worth your precious time will stick around... even when you bleed on their expensive sheets.

Cool people who are worth your precious time will stick around... even when you bleed on the sheets.

So here are 30 dating fails everyone needs to get out of their system in their 20s:

1. Accidentally calling your date your ex's name.

2. Accidentally spending the entire date talking about your ex.

3. Strutting around like you're the hottest shit on the planet, only to realize you have a giant bloodstain on the ass of your stark-white jeans.

4. Realizing you're on a date with someone who doesn't think this is an actual DATE. Meanwhile, you spent $50 on a blowout and 10 hours strategizing the evening with your friends.

5. Showing up for a Tinder date, only to realize you were catfished, and your date looks absolutely nothing like they did in the picture.

6. Overbooking your Tinder dates and realizing you have two different people coming to the same bar at the same time.

7. Farting on your date. I don't even need to get into anymore details. It always leads to a shame spiral of epic proportions.

8. Accidentally having too many "personality drinks" pre-date, going to your date wasted, trying to cover it up and failing miserably.

9. Coming to the bitter conclusion halfway through your date that you have no idea what your date's fucking NAME is.

10. Running into your hookup from the night before while on a date with someone you really like.

11. Breaking a heel before your date and hobbling into the restaurant with a snapped-off platform in your purse.

12. Accidentally saying "I love you" instead of "goodnight" on A FIRST DATE.

13. Your date reaching for your hair while you're kissing passionately and provocatively giving it a tug, only to have your clip-in hair extension come out in your date's hand. Your date screams bloody murder.

14. Having your date accidentally call you their ex-girlfriend's name twice in 20 minutes.

15. Going on a rebound date after you've just broken up with someone and bursting into tears before your second glass of champagne has the chance to come out.

16. Throwing up for whatever reason. Maybe you're drunk, maybe you're just sick or maybe you're just terrified. But regeardless, vomiting on a date fuels your desire to change your last name and immigrate to Australia.

17. Having your credit card declined on a date after you ordered the most expensive thing on the menu to seem "cultured."

18. Realizing you accidentally left your wallet at home and realizing that confessing to it sounds like the worst excuse possible.

19. Mispronouncing an exotic item on the menu and getting corrected by the waiter.

20. Running into your drunk friends, who feel the need to discuss loudly how wasted you were last weekend and how you took your clothes off and ran through the park naked. This, of course, happens when you're on a date with a civilized, older person.

21. Going on a sexy oyster and champagne date, having an allergic reaction to the oysters and having your face swell twice its size right before your date's terrified eyes.

22. Lying and saying "Ew, I don't smoke" on a date, only to be caught red-handed smoking at an outdoor bar three nights later.

23. Going on a sexy beach date, only to realize people aren't staring at you because your string bikini is chic; they're staring at you because your tampon string is hanging out the side of your scanty bikini bottoms.

24. Making a totally offensive, off-color joke because you're nervous AF and trying too hard. They now think you're a bigot.

25. Accidentally pocket-dialing a new person you've seen a few times the very moment you and your friends are discussing bodily functions, pubic hair, exes, crushes and bad hookups. You realize you've left them a 30-minute voicemail.

26. Accidentally taking a Xanax instead of an Advil before a third date with someone you really like, who is really sharp, and you become a zombie.

27. Having all of your antidepressants — Prozac, Valium and Wellbutrin — come tumbling out of your purse as your date stares at you in horror. Of course, you feel the need to yelp, "Oh, those are my friend's pills!"

28. Pressing your date to tell you ALL about their ex because you're curious and have terrible boundaries. Then, they tell you their EX IS DEAD, and the mood is ruined.

29. Trying to act super cool and aloof at a swanky restaurant, but choking on a piece of bread, causing a huge scene and needing the Heimlich maneuver instead.

30. Realizing midway through the date you hate the person you're on a date with. They've been shaming you about everything, and they're criticizing every single entity at the bar, but you still stay on the date. Maybe you even go home with them because you don't know how to say no yet.

When you come home the next morning, you're ashamed you let someone treat you so badly, and you vow never to waste your time with assholes like this ever again. And that epiphany alone makes going home with the wrong person so totally worth it.

Some lessons you need to learn the hard way.