My Worst Date
My Worst Date

My Bloody Valentine

by Damien Wood 2 years ago in dating

The Worst First Date Ever

My Bloody Valentine


It was early February of 2011. I was having lunch with my friend, Tristan, at McAllister's deli, when the subject of a mutual female acquaintance of ours came up. She was in our Anatomy and Physiology lab group, but I never hung out with her much outside of class. However, she was good friends with Tristan. I honestly thought the two of them had been dating in the month after she broke up with her previous boyfriend, so what Tristan said to me next caught me completely by surprise in more ways than one.

"Say, Damien, you know that Kelly has a thing for you, right?" he said.

"What?" I replied. "As much time as the two of you spend together, I thought you guys were dating."

"Dude, are you really that clueless?" he asked.

"I... guess so," I answered. "What do you mean?"

"Oh my God, dude!" he exclaimed. "I'm gay!"

"What? Really?" I asked.

"Yes!" he shouted, sounding exasperated. "Really dude, how often do we hang out? You mean to tell me you really haven't figured it out by now?"

"Um, I guess I just never thought about it," I replied. "So... Congratulations, I guess."

"Fuck off," Tristan replied, fixing me with a piercing glare.

It was true that it had never crossed my mind that Tristan might be gay. He was a bit more effeminate than most guys I knew, but I just figured it was because he was an emo rocker. His hair was about ear-length, dyed bright green and combed over to one side. He wore eye shadow and black clothes with a wallet chain between the front and back pockets on his pants. Ever-present around his neck was a leather choke-necklace with metal spikes.

"What, dude?" I said. "What do you want me to say? I don't really care if you're gay."

"Okay," he said, his expression softening. "Anyway, what do you think about Kelly?"

"I think she's very attractive," I replied. "But I don't know her well enough to know if I'd like her as a person."

I actually thought that Kelly was way out of my league. She was twenty years old, three years younger than I was. Her hair was strawberry-blonde and she had the brightest blue eyes I had ever seen. She was also fairly tall, about 5'11", and had a striking figure. Also, she was very intelligent, as evidenced by how well she did in our Anatomy and Physiology lab group. We were all very thankful that she was there to help us out because, if she hadn't been in our group, the rest of us would most likely be close to failing.

"Well, maybe you should take her on a date," Tristan suggested. "She actually wanted me to ask you out for her."

"Really?" I asked. "That seems like a rather girlish, high school thing to do."

"Don't be a dick," Tristan replied. "Besides, she's a lot nicer than most of the girls you've been with. Remember the girl who tricked you into getting a chlamydia test?"

"Ouch! Good point," I said, wincing at the memory of what had happened to me a year ago. "Well, I suppose the worst that could happen is that I end up having the worst date ever."

"Don't be so optimistic," Tristan replied sarcastically. "I'll tell you what though, I'm pretty sure she'll put out for you. She's been whining to me for almost two weeks about how she needs to get laid. Plus, she knows you're a carpet muncher."

"How does she know that?" I asked.

"You're reputation precedes you, man," he answered. "Plus, I told her. Anyway, I'll set it up so that we hang out during lunch in a couple of days. Just give her a chance, dude. I think you'll like her."

True to his word, Tristan invited Kelly and I to lunch in the college cafeteria a couple of days later. Apparently, he hadn't told Kelly about his brilliant plan to bring us together. She was the last to arrive at our corner table. When she saw me sitting there she turned beet red and sat next to Tristan. I was amused to see her so embarrassed, but also confused. She was far more attractive than I was, so I had no idea why she could possibly have such a crush on me.

"So, Kelly," Tristan said. "Valentine's Day is this weekend and both you and Damien are single. Why don't you two go on a date?"

"Tristan!" she exclaimed.

"What?" he replied. "You wanted me to ask him out for you, didn't you?"

"Yeah, but..." she stammered.

"Really smooth, buddy," I said, chuckling.

"Well, it's true," Tristan replied. "I know for a fact that neither of you has a date. And I'm getting pretty tired of hearing about how much you want Damien to ask you out, Kelly. So how 'bout it?"

"Yeah, how 'bout it, Kelly," I teasingly said. "I promise I don't bite."

"Okay," she mumbled. She then gave me her phone number and wrote down directions to her apartment. We finished our lunch, making awkward small talk about lab as we did so. When we got up to leave I went over to Kelly and smiled.

"Don't be so nervous," I told her. "I'll be a perfect gentleman. I promise." She smiled back warmly and gave me a friendly side-hug.

I arrived at Kelly's apartment at 5PM on Valentine's Day to pick her up. We both loved seafood, so we had decided to eat at Red Lobster. I had brought a single rose with me, thinking that a whole bouquet and a box of chocolates would be a bit presumptuous. When I knocked on the door, her roommate answered. After giving me a contemptuous look-over, she stepped aside and let me in.

Her apartment smelled faintly of lavender and marijuana. As I looked around, I noticed that it was neatly made up. This didn't surprise me, as fastidious at school as Kelly was. However, the coffee table was littered with soda cans, junk food and a large bong. Kelly's roommate motioned for me to sit in the armchair next to the coffee table. "Kelly should be out in just a few minutes," she informed me.

"Thanks," I replied. Kelly's roommate proceeded to sit on the couch and take a huge rip from the bong. She then looked at me appraisingly as she blew out the smoke.

"So you're the date?" she asked.

"Yeah," I replied. "Do I meet your approval?"

"You're not as cute as her ex," she accusingly replied. "You better not be as big of a piece of shit as he was."

"I'll do my best," I answered sardonically. Kelly emerged from her bedroom at that moment, looking absolutely gorgeous. Her hair was made up in a wavy pattern. She wore simple pearl earrings, a spaghetti-strap red dress that was cut just below the knees and matching, two-inch, red heels. Her make-up was lightly, yet tastefully done. I felt underdressed, wearing a simple dress shirt and black jeans.

"I'm ready," she said, smiling.

"You look amazing," I told her.

"Thanks!" she replied. She gestured toward her roommate. "I see you've met Rhonda."

"She seems like a wonderful person," I answered with mock sincerity. Rhonda scoffed and took another huge rip from the bong. Kelly hid a smirk behind her hand. "Oh, I almost forgot," I said, handing her the rose.

"Aw, you shouldn't have," she replied, blushing as she took the rose. She then looked around the apartment. After she saw that she had nowhere else to put the rose, she walked over to the coffee table and put it in Rhonda's bong.

"Hey!" Rhonda protested.

"Maybe it will make the smoke taste better," Kelly suggested. I found myself laughing in spite of the fact that she'd just dumped the rose in bong water. Kelly then looked at me and said, "Shall we?"

Kelly seemed to loosen up on our drive to Red Lobster. I asked her if she liked "The Killers" and she replied with and enthusiastic, "I love them!" I smiled and put in their Sam's Town CD. We mostly talked about school on they way: how difficult the class was, how the lab was excruciatingly long, how funny it was when the professor accidentally illustrated multiple axons stimulating a single one as multiple penises ejaculating all over a single unfortunate one.

The dinner itself was pleasant, but largely uneventful. We made small talk getting to know one another better. I turned out that we had a lot more in common than we thought. We had pretty much the same taste in music and movies. She was also an avid Quentin Tarantino fan, which further endeared her to me. I was also delighted to find out that even though she acknowledged that vegan diets are healthy, it's ridiculous to expect the rest of humanity to refrain from eating meat.

After dinner we decided to see No Strings Attached. We skipped the popcorn and just got a couple of drinks. I was delighted that she was completely comfortable watching the sex scenes with me. She even leaned over and cuddled up to me less than halfway through the movie. As the movie was reaching its conclusion, I thought to myself, "Wow, I think I like this girl. She's smart, funny, and incredibly beautiful. I don't know what I was so worried about. I think this may be the best date I've ever been on!"

When we got back to my car, she turned to me and said, "Thank you for tonight, Damien. It was a great dinner and an even better movie."

"It was no trouble at all," I replied, smiling. "I think I enjoyed myself just as much as you did."

"Really? Because it looked like you were gonna cry a couple of times," she teased.

"What can I say?" I replied, scrunching up my face like I was about to cry. "That musical number reminded me of my high school prom."

"Ah! You're terrible!" she exclaimed. We stood their laughing at our little inside joke for a few seconds. When we finished laughing our eyes locked. I had seen that look before, so I was pretty sure she wanted me to kiss her. Throwing caution to the wind, I went for it. My assumption proved correct as she put her hands around the back of my neck and pulled me in. When we pulled apart, I felt an amazing tingling sensation in the back of my neck.

"What do you want to do now?" I asked.

"It's getting late," she replied. "Why don't you take me home?"

"Oh, okay," I said, feeling disappointed.

We pulled up in front of her apartment about fifteen minutes later. I put the car in park and looked over at her. "Well, here we are," I said. "Can I walk you to the door?"

"I would like that," she replied. I turned off the ignition and we both got out of the car. We held hands on the way up the stairs and to the door. When we arrived, we turned to face each other. She was looking at me expectantly, so I leaned in for another kiss. Before I could reach her, she put two fingers up to my lips. "Want to come inside?"

"Sure," I answered, trying not to sound like the excited little boy that I felt like. She winked at me as she opened the door and let me inside. Rhonda was thankfully nowhere to be found. Kelly went to the kitchen to grab a bottle of wine. I asked her teasingly, "Aren't you too young to drink?"

"I'm sure you waited until you were the legal age to drink," she replied sarcastically. "Besides, it's Rhonda's. I imagine she's probably downed about three or four of these by now, so I doubt she'll miss this one."

"Oh, I wondered what happened to her," I said. Kelly looked at me, raised an eyebrow and smirked. I sheepishly admitted, "Okay, I honestly didn't even care."

She turned on the TV to some movie channel, but I couldn't tell you what was playing. We had a few glasses of wine and made small talk for a while before our hormones finally took over. Before I knew it, we were wrapped in each others arms and making out. I managed to kick off my shoes as the booze fueled our passions. When I started to feel her breasts, she pulled away from me. She then stood up, took me by the hand and led me to the bedroom.

Once she closed the door behind us, we began frantically disrobing. I managed to tear a couple of buttons off my shirt in my haste to get it off. She easily slipped out of her dress, bra and panties. I noticed that her underwear was the same shade of red as her dress. When we were both naked, she pulled me to the bed.

"Go down on me," she whispered after a few more minutes of making out and caressing each other. I happily obliged. Working my way down her body, I kissed her neck, shoulders, breasts, sternum, navel, mons pubis and finally made my way to her inner thighs. When I felt like she was finally ready I started licking the labia themselves.

I started with the outer labia, slowly warming her up. I then licked the inner labia, working my way around the clitoris. She gasped in ecstasy as I found the right spot, guiding me with her body and squeezing my head with her legs. She had a slight, musky scent about her, which was normal in my experience. However, when I licked between her inner labia, I noticed a slight, coppery taste.

"What the hell is that?" I wondered. When I pulled away to look, she grabbed the back of my head and thrust my face back into her. I did my best to try and ignore the taste, but it kept getting stronger and stronger. When I finally couldn't take it anymore, I forcefully pulled my head out of her surprisingly strong grip. I looked down and, to my horror, saw fresh blood between her legs and on the sheets.

"Please, don't stop!" she exclaimed, trying to grab my head and pull me back in. However, I managed to jump back off the bed and stand up.

"Ugh!" I screamed. "What the... Oh, my God! What the literal, bloody fuck!" I reached up and gingerly touched my lips. To my disgust, I found that they were caked in blood. I started gagging as the realization of what had just happened hit me. One of my worst nightmares had come true: I had just inadvertently earned my red wings.

"What's wrong?" Kelly cried from the bed.

"You... Look at my face!" I exclaimed. "Look between your legs! Look at your sheets!" She looked from my face, to her sheets and finally between her legs. The looked on her face went from puzzlement to horror as the realization of what was happening dawned on her.

"Oh, shit!" she gasped. "It must have just started." Adrenaline was coursing through my body, causing my mind to race.

"Is that the reason you were wearing all red tonight?" I asked incredulously. "So that if you spotted it wouldn't show?"


"Ugh! I'm going home!" I proclaimed.

"Oh, my God!" she said, suddenly sounding aggravated. "Do you really think that you are the first guy this has ever happened to? Why don't you stop being such a fucking pussy and come finish me off?" I stood there momentarily stunned. On the one hand I was disgusted. On the other hand, my masculinity had just been challenged. She then rolled her eyes and said, "I promise I won't make you go down on me anymore."

In the end, my sense of masculinity won out over my disgust. After all, I was still a young man with everything to prove. I looked up at her and said, "Fair enough. Just let me go wash out my mouth real quick."

After rinsing out my mouth with plenty of mouthwash and water, I returned to the bedroom. I went over to my pants and pulled a condom out of the camera pocket. When Kelly saw me do this, she asked, "What the fuck do you need that for?"

"What? I was gonna wear it anyway," I replied. "Besides, I'd rather not have period blood all over my dick."

"Ugh! Whatever! Just hurry the fuck up!" I suppose the adrenaline had kept me hard where my disgust might have otherwise caused me to lose my erection. I had the condom on in a few seconds and was in bed with her an instant later. We didn't wasted any more time with foreplay and were done within a few minutes. The sex was less passionate than before and more angry. I'm not sure if I gave her the orgasm she had been wanting, or if she faked it. At that point I could have cared less.

After we had taken a shower and gotten dressed, we stood in her bedroom for a few moments in awkward silence. "You can sleep here tonight," she finally said. "I'll change the sheets so you don't have to sleep on the couch. I know this is weird, but I don't want you driving home after drinking all that wine with me."

"Thanks for that," I replied. I had calmed down considerably in the past half hour. I was no longer angry or disgusted, just ashamed at what I had done and how I had behaved earlier. What I really needed at the moment was a cigarette. "Do you wanna smoke a cigarette with me outside? Maybe get some fresh air?"

"Sure," she replied. "I don't smoke that often, but I could use one too. Should we finish the wine as well?"

"Why not?" I replied. "We might as well." We tried to clear the air between us as best we could while we were outside. I think we were both embarrassed about what had happened. I asked her, "So why didn't you tell me you were on your period? Don't you think I would like to have known that before I got my face all bloody?"

"I honestly thought I wouldn't get it for a couple of days," she replied. "I'm really sorry. It wasn't intentional."

"So you wearing all red was just a coincidence?" I asked quizzically.

"I wanted to look my best for you," she answered. "I had a crush on you even before my ex broke up with me. I hope you aren't too mad at me."

"No," I said after pondering it for a few seconds. "I'm not. I was pretty pissed at first, but if you didn't know, you didn't know. It's over now."

"Was it really that bad?" she asked.

"That was the grossest tasting thing ever," I replied. "I can't think of anything quite that bad happening to me before."

"What about the girl who tricked you into getting tested for chlamydia?" she asked, barely concealing a smirk.

"Who told you about that?"

"Tristan," she replied, now breaking out into a giggle.

"That fucking asshole!" I softly exclaimed. "Fair enough. It wasn't quite as bad as that." We both shared a laugh, then finished our cigarettes in silence.

"Want to go to bed now?" she asked.

"Sure, I'm exhausted," I replied. I then turned to face her. "Look, I don't want there to be any hard feelings between us. I still think you are amazing, in spite of what happened tonight. In fact, I had a really good time with you up until that unfortunate... incident. So would you... I dunno... Would you like to have breakfast with me tomorrow?" She seemed to ponder my question for an eternity, but it was probably no more than a few seconds. "You don't have to if..."

"I would love to," she finally answered. "I think it's best if we put this behind us because I really like you too."

"Great," I said, breathing a sigh of relief. "Can I ask you a favor though?"

"Go for it," she replied.

"If we ever, you know, hook up again, would you at least give me some warning if you are close to your time of the month?"

"I guess so," she said, giggling. "I guess I owe it to you after this."

"Also, let's never speak of this again after tonight."

"Deal," she replied, grinning from ear to ear. With that said, she took me by the hand, led me inside and off to bed.

In spite of that traumatizing ordeal, Kelly and I ended up dating for about six months or so. We had a very good relationship and only ended it because she ended up pursuing the rest of her degree at an out-of-town university. True to her word, she warned me every time I was about to go down on her when she was close to her time of the month.


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Read next: 'Chocolate Kisses'
Damien Wood

I've come to find that writing is a potent form of catharsis for me.

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