I’ve enjoyed dating, and think I’m pretty good at it. But once it in a while, I do something really stupid, embarrassing, or just plain terrible. I guess it happens to all of us. We get a little nervous, anxious, and make a few mistakes.
We all have bad dating stories, but rarely do we blame our self. It’s always something the other person does. So I think it’s only fair to divulge some of my personal worst dating disasters. Hopefully, they will serve as lessons for all of us.
The Pub Crawl (Pub Golf)
Even though I screwed this up big time, it was still one of the best days of my life. The pub crawl or pub golf was an extraordinary experience. It was a golf themed event so people dressed up in their coolest, goofiest, and sexiest golf outfits. I wore khaki pants, a Nike warm-up jacket, a golf glove, and the kicker was a plaid beret. It was a painful gift from a former girlfriend. I am not a beret guy. I didn’t have good use for it, until now.
I didn’t know many participants, but was just glad to be at the bar. It turned out to be 21 guys and 21 girls. Everyone was cool, and 2/3 of the girls had the killer of combination of being single and also really cute. And they looked especially hot in their golf attire. It was an incredible stroke of luck. I would be spending the day with attractive and available women, and we’d all be getting drunk at the same time. Unreal!
The pub crawl was extremely well organized. We were split into groups of six, 3 guys and 3 girls per group. Each bar served as a hole. We were given score cards to indicate what score we would receive. For example, for par, it was one drink per person. For birdie, it was one drink and one shot. And the list went on.
Each bar got progressively more challenging with types of drinks (Irish Car bombs, Absinth, chug offs, etc), and I was up for the challenge. Our team birdied the first four holes. We were on fire.
As the liquor flowed so did the conversation. I hit it off with a new girl at each bar. I was having the time of my life. I felt like Tiger Woods. Each girl was cute, sweet, and fun to talk with. It was like speed dating, but with alcohol and the coolest girls ever. I ended up garnering four phone numbers. The crawl was a success, but I was in way over my head.
A few days later, I examined my collection of numbers, and that’s when I blew it. Instead of focusing on the girl l liked the most, I figured why not call of them. I was single. I was cool. I was funny. At least this is what was floating in my head.
I had fun talking to them. I was being mathematical and skeptical at the same time. There was no way all four would like me again or even call me back. I assumed three dates would be okay, and one would be very good. I just wasn’t sure who the “very good” would be.
So I contacted all four girls. Unbeknownst to me, THEY ALL KNEW EACH OTHER. It made sense since we all went to the same event. But because I’m a complete idiot, I never really thought about that. A private source (my friend who knows them and later told me the story) informed me about the debacle. As soon as I asked them all out, they contacted each other and confirmed that I was pretty much a jerk. I should’ve just sent a group email and cut out the middle man. At least that would have been more direct. Obviously, none of the girls responded.
They were right. I was a jerk. I blew it. It was a lot like golf. I got to the green in just a few shots, and had a chance for a birdie. But then I four putted my way to the triple-bogey. I was just in way too deep. I can barely handle one girl let alone four. But I guess pub golf can be a tricky game sometimes.
The Bottle of Wine
It was my fourth date with Jeanne and I was ready to bring her to my favorite restaurant in LA: The Sauce Place. It was one of those mom and pop Italian places that only took cash and where you could bring your own booze. They were known for their delicious desserts, and I absolutely loved the marinara sauce.
Jeanne immediately liked the place and was impressed when I pulled out a fresh bottle of wine. The waitress handed me an old school corkscrew—I guess I would be opening the bottle.
I screwed up on my first attempt to uncork the wine. Jeanne laughed and I shrugged it off. It wasn’t too big of a deal. But then it got worse. I tried and failed once again. Either this corkscrew was busted or I was a complete moron. I started to get angry and then I panicked. I tried again. The screw finally went in, but now I couldn’t pull the damn cork out. I was pulling with all of my might. My face was flushed. I was sweating. I was pissed. Meanwhile, Jeanne was slowly hiding behind her menu in embarrassment.
I was now in a one-on-one battle with this bottle of wine. I finally pulled one more time, and ripped the cork out of there. There was only one problem. Half of the cork still remained inside.
The waitress eventually came over and used a knife to fish the cork out. Tiny pieces fell into the bottle, but at least we could finally drink it.
The night was a bust, and somehow got worse. I raved about the desserts all night long. After dinner, Jeanne’s eyes widened as she decided between the gelato, cheesecake, and homemade cannolis. That’s when I realized I didn’t bring enough cash, and there was no ATM within sight. When the waitress stopped by for our dessert order, I quickly dismissed her and asked for the check. Jeanne stared at me in confusion.
I dropped Jeanne off at her apartment and we hugged good night. She flashed a bright smile even though I knew she was faking it. I was disappointed because I really liked her. If it weren’t for that damn bottle of wine, everything would’ve been fine.
I waved goodbye and assumed I’d never see her again. I called a few days later and left a message. To my shock, she called me right back. And we ended up dating for nearly a year.
A few months later I asked her the big question: “Why did you want to go out with me after that horrible wine incident?” The answer: She thought it was cute.
I’ll always remember this story. It’s taught me the greatest lesson of all: if you do something stupid on a date, something embarrassing, something painful and you’re with the right person, they’ll think it’s cute. So it’s okay to mess up sometimes.
I met this super cute girl at a bar. She went to school in Boston, liked the Sox, and had a killer body. We went on a date to discover that we actually didn’t have much in common. We disagreed with just about everything, and although it made for decent conversation, it was stressing me out.
My flirting skills were weak that night. I was tired, had a long day, and wasn’t feeling it. It was no excuse, but she was driving me nuts. After another debate, I joked around, said that she was driving me nuts, and if we kept disagreeing I was gonna “kill” her. No matter how cute, charming, or funny you are, this is not a good line to use on a first date. My hope was that it would be cute, silly and flirty, but it definitely came through as weird, creepy, and awful.
As I walked home alone, I realized she now had a dating story. She had a tale about the weirdo who threatened to knock her off. I felt like a complete moron. The only saving grace was that she did respond to my apology text and said everything was okay. But I think she only sent it out of fear.
I was on a date with a pretty Asian girl. We were downing our drinks, and flirting, talking about our favorite places to travel. She made eye contact and smiled a lot. Things were going in the right direction.
That’s when I told her my passion for writing. She asked if I was working on anything. I told her about this blog. She instantly took out her new age phone, pressed a few buttons, and my blog stood before us. She perused through it, landed on my DEALBREAKERS post, and chuckled a few times. Then she asked me lots of defensive questions. Then things got a little uncomfortable. Then I never heard from her again. I learned my lesson: never show off my blog on the first date.
The Blog II
Of course, I broke that rule again. This time my blog served as a connection at first. She loved my writing, and that made me feel great. She encouraged me to submit to magazines, newspapers, and even write a book. All was well until she critiqued my latest post entitled THE BOY COLLECTOR and she took offense to it. She thought it was misogynistic (it probably was), and I was calling her out (I wasn’t.) And then she feared if I wasn’t, I soon would. She assumed that I would embarrass her on my blog. I promised I would never do that (until now), but by then it was too late. Things got awkward, and I was paranoid that she would overanalyze all of my blog pieces. I proposed dedicating a blog post to her, but by then I realized this relationship was just not going to work. Once again I learned to keep my blog to myself.
The Double Header
One night, I tried to be suave and plan two dates in a night. My theory was that one girl would cancel anyways so it was more of a safety plan. But to my surprise both girls actually followed through. So I had my first date at 7pm and the next at 830pm.
The 7pm date was actually going well. But I kept excusing myself to text to my second date that I was running late. I was constantly checking my cell phone. My date caught onto this, and could definitely tell I was not paying attention to her. In my head, I was being smooth, but I definitely wasn’t. She probably didn’t know I was scheduling my second date of the evening, but she did know I was being a jerk.
The first date was a failure, but at least I had a second chance with the 830 girl. I arrived on time, but she never showed up. I finally received a text. She was going to flake, and I wondered if she pulled the same stunt as me. Maybe she was already on a successful date so she didn’t need me as a backup. I guess I deserved that. Karma’s a bitch.
The Easter Call
Never call a girl for the first time during Easter dinner. I learned this lesson with Eliza Dushku, but you can click here for the full story. Once again, I am an idiot.
The Sweaty Pig
I was enjoying my friend’s concert when I realized I was late for my date. It was about 20 blocks away (a mile or so), and it started in ten minutes. I hated being late, and out of principle, I just couldn’t take a taxi (it was too short of a distance) so I ran for it.
At the time, I was running everywhere: to meet friends to watch football, to the ATM, and now to dates.
The good news was that I was physically fit and showed up on time. The bad news: I was a sweaty pig. The girl greeted with me a hug and literally slipped off of me. I was a nasty mess. For the first ten minutes, I caught my breath, and mopped down my brow with a napkin. She looked at me with disgust as she tried to make conversation.
I had embarrassed myself with my sweaty pig routine. But at least I was punctual. Rightfully so, I never heard from her again.
The Tucson Girls
About a decade ago, I drove cross-country with one of my best friends. He and I ended up in Tucson, Arizona for the night. It was one of the best places I’ve ever been. It was a land filled with healthy, fit, tan, and gorgeous college girls.
The bars were stocked with these beautiful goddesses from the University of Arizona. Not only were they beautiful, but they knew how to party and had loose morals too. It was a stark contrast to my days at Tufts where the girls didn’t like me and had much higher standards.
My buddy and I met a pair of buxom blondes. They liked that we were traveling cross-country and showed their affection by buying us drinks and touching my leg. In my head, I kept thinking of the perfect line so we could go back to their place. As I scoured my brain, one of the blondes abruptly asked: “Wanna come back to our place?” It was brilliant. Why hadn’t I thought of that?
The girls jotted down the address on my bar receipt. I calmly placed it in my pocket, but I could barely contain my excitement. The blondes had to walk a friend home, but we would meet them at their place in an hour.
My buddy and I galloped back to our motel, sprayed on some cologne, and pre-congratulated each other on a job well done. We had permanent grins. It was the perfect night.
Then we jumped in our car and drove to their place. But we never arrived.
We searched and searched, but we never saw them again. The address did not exist.
In her haste, the buxom blonde forgot one number on the address. But we didn’t know which one. We drove for hours, knocking on doors, waking up people, praying, fighting, and finally giving up.
In my haste, I never got a phone number, and realized I blew it. I contemplated whether the girls were just messing with us, but I think it was an innocent mistake. They probably waited by the door for us and wondered why we never showed. Then they gave up and settled for a good old-fashioned pillow fight in their bras and panties.
I still have the address somewhere in my closet in an old shoebox. It serves as humble pie and what might have been.
So the next time you’re on a date and you screw up, do something stupid, or make a fool of yourself, just think of me, and maybe you’ll feel better. And if not, at least you’ll have a good story for your friends.