5 Bad Date Stories That Will Make You Feel Better About Yours

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Girl cheering up her friend

Laugh to get through.

Dating has never been my forte, as I'm forever believing that I'm not meant to do the juggling thing. But every now and then I get in a little groove of dating, and although nothing good really ever comes of it as far as building goes. I do end up with the most hilarious bad date stories that I'll one day be able to share with my kids when they're old enough to endure their own dating struggles. 

If I were a little more consistent in my dating life, I'd probably go as far as to say I deserve some type of camera crew following me around because things get that real.

I've had cross-dressers ask me out, and I've actually been out with potentially closeted men. But you know what? I never let those types of little things stop me. Fortunately, I have a personality where I can laugh it off — and sometimes you seriously have to.

Because I know someone somewhere probably has a similarly terrible dating life ever, I decided to share these 5 of my hilarious bad date stories that are bound to make you laugh and feel 10 times better about your own situation.

1. Famished for Love

After months of this guy trying desperately to talk to me and my resisting because of petty mishaps (like him asking me what a hiatus was as opposed to looking it up himself), I finally gave this guy Gary a chance to take me out.

The first red flag should've been when he blew me off to make up for the many times in the past that I had crushed his ego. However, I tried to be understanding, and we rescheduled with plans for dinner on a Thursday night.

Living in Hampton, Virginia, there weren't too many options so we settled on Joe's Crab Shack. While my date was initially excited to get himself a drink, his excitement quickly deflated when he noticed the drink prices and settled on water ... for both of us.

The next thing I knew I was being forced to share the Ragin' Cajun Steam Pot that I on any given day would be able to finish off by myself in five minutes tops. We sat there like animals rushing to grab food as if we were playing in the Hunger Games ourselves, making sure we got our fill.

Although I was annoyed I made the best of the date and after coming to the obvious realization that neither of us was full, he ordered us another bucket to share AND THAT'S WHEN IT HAPPENED.

That's when he picked up the plate with leftover seasoning and sauce on it and began licking the plate in circular motions. That's when I knew there would never be another date.

I will shamelessly lick a plate clean in the comfort of my house but in the middle of a public restaurant? Lord, I was mortified. And, this is when I realized I shouldn't have relaxed my standards, which had kept me from going out with this guy for the previous two years.

2. Lady in Code Red

This was one of my first real dates. I was in college, and I was excited by the effort that the guy made.

Joe picked me up from my apartment, and we went somewhere thoughtful (a military museum on the beach). A gentleman, no doubt.

But as we were walking around the beach we bumped into another couple taking a romantic trek and things got super awkward fast.

Joe randomly blurted out how he wanted to perform oral sex on the man we saw walking along with his female partner. From what I can remember (because I do think I might've tried to mentally block it out) his reasoning was because he loved seeing other men actually court women.

As the night went on he continued to tell me how his father always thought he was gay growing up, but he didn't think that he himself just thought he had feminine tendencies.

About that time, I politely claimed to be tired and went home never to go out with that interesting fella again.

And you know what he might not have been gay, but I wasn't willing to be the girlfriend he decided to come out on years later. Sorry-not-sorry.

3. So Sorry

I was about to move away from New York when I went on a date with a guy named Miles, whom I'd met through a mutual friend.

We had some of the best conversation I'd had in awhile, and things weren't awkward at all.

He was sweet, but we were both in transitional positions since I was moving away in two weeks and he had just broken up with a long-term girlfriend about three weeks earlier. So, we agreed that we were both on this date with the intention to be open to possibilities in the future without looking for anything in the present.  

We extended our date by going to a game bar with giant Jenga and Connect Four. He posed as my photographer for the night, taking any silly picture of me that I asked him to, which is always a win for a modern girl and we hit it off. 

I didn't expect anything to go further, because of the whole bad timing thing.

However, when we pulled up in front of my apartment he had something quite different in mind as he leaned in for what I thought was going to be a kiss on the cheek, he actually tongued down my closed mouth (which I actively refused to open) and then embarrassingly apologized after I yelped "what the hell! You wet my whole face. What was that?"

He profusely apologized and even sent a text apologizing but that would definitely be the last time he texted me. I probably shouldn't have been so blunt about it, huh?

4. Illiterately Misread 

Will invited me to the spa, and it was a setup where you pay a set fee and have access to the pool and hot tub, but that fee didn't include a massage.

He clearly put zero thought into the planning process because when we get there all the massage tables were booked. So, we were forced to sauna hop and suffocate from the ridiculously high levels of chlorine that filled that pool.

This annoyed me, as I anticipated a massage and probably because I wasn't that into the guy.

As the night went on, we grabbed some food and he talked about his ailing grandfather ad nauseum. Meanwhile, I'm texting my ex — yeh, a clear sign that I just wasn't interested.

After grabbing dessert, which included ice cream, I told him goodnight and ran in my apartment without the slightest invite for him to eat his dessert before it melted.

I had allowed this guy to leave a bag at my apartment so he didn't have to carry it around, and when we got back he came in to get it. He took this as a cue to sit down. Me? Well, hell no — I'm just thinking in my best Mean Girls voice "You can't sit with us!" but he was so painfully oblivious to my yawns that I went into my room put on my dingiest, most kiddy looking mou-mou and wrapped my hair to get ready for bed, and began hinting at being tired. 

Now, had we been together this might be a sign for sex but because I'm a woman the likelihood that I'm going to set the mood for first time sex in a mou-mou and scarf is very unlikely.

And what's even more unlikely is that I'd want to sleep with a man after a year of us hanging and never kissing or even hugging. Yet once this guy left my house he felt that he had "misread the signs."

He literally sent me four paragraphs saying he should've made a move on me because that's what I wanted. 

Fast forward months down the road, as this guy still continues to ask me out even though I'm a grade-A asshole. (Yes, I know I'll probably be served a cold dish of karma.)

5. Awkward

This one isn't so bad, but it was still pretty awkward.

I was on this unheard of dating app called Clover for awhile and I finally found someone (Jason) who I didn't feel awkward communicating back and forth with.

But that changed once we weren't behind hiding safely behind text messages. We finished our date and I clawed my way out of riding the train with him to spare me any more awkwardness.

We both knew this wasn't going anywhere else, but after a couple of days he messaged me on the App and was like "oh, I see you're already looking for new guys. I see you online." 


Who does that? We went on one date ... just let the sh*t go.

As awful as each one of these dates has been in the moment, I've found a way to laugh about this moments, and no I don't even wait years after the fact. I just laugh it off right in the moment and share with my friends because this is what being single is all about: Laughing and laughing hard at all the wrong people until you find someone to laugh with. Kidding. Kind of. 

*All names have been changed to protect the identity of the individuals.