The biggest mistake I’ve ever made is not making this blog anonymous.
That said, I wish I had more freedom to post about dating aspect of my life because it is hiiiiiiiiiighly entertaining and I’m pretty sure the readership would allow me to quit my day job and blog forever. Plus you readers seem to enjoy it! Out of respect for all parties involved, I’m a 9-5er (ahem 8-6er) and sit in a cube staring at Excel sheets all day.
I would however like to highlight some of my more memorable/hilarious/horrendous/wtf dating moments and contribute to the ‘Sh*t [insert group of people here] Say‘ movement on YouTube. Here’s to hoping that those guys either a) don’t read my blog, and/or b) don’t realize I’m talking about them! But really… it’s just too ridiculous not to share.
Here we go:
“I’ll let you get this one…” said to me by a guy that had [at one point] piqued my interest as he passive aggressively had me buy tickets to a show that he told me he already purchased tickets for. I have no problem pitching in and will always (always, always) offer but he didn’t even let me get that far! Needless to say, that was the only “one.” Next.
“If you’re looking to ease back into dating… I’m a really easy guy to date” said to me a couple weeks after my breakup of the century. I wonder how long he sat around thinking of that line, or how many times he’s used it before. Nevermind, I don’t want to know.
“Yeah – I’ll miss you too. But I’m kind of more one of those ‘out of sight, out of mind’ people. So I mean… I’ll be really excited when you come visit, but other than that it’ll probably not be a huge deal.” We never went out, but really boys?? I can take a hint but you could have at least lied a little!
“I want to tell you that I like you, but I don’t want to be another Sarah Iverson Statistic” — Can someone tell me what that means exactly??
I was out with a group of people very recently and here is a conversation with a guy I had met earlier that night:
Him: Hey! So I know your ex. (Of course you do. Mind you I had never met this guy, I’m in a new city, far away from anyone that would have even known I had an ex.. much less who he was.)
Me: Oh really? That’s great ((fake smile))
Him: Yeah… he’s a really great guy
Me: Yup – he is
Him: I’m really sorry about everything that happened. (It’s been over a year) He really is such a good guy.
—————————- silence —————————————
Him: So would you like to go on a date with me tomorrow?
Me: No thank you.
“I know this is weird, but it feels kind of good to see you hurting — I feel like you are kind of getting a glimpse of what I’ve been going through” — says the guy that apparently had a crush on me for a long time and it was never reciprocated. This might be why it didn’t work out between us…
“Sweeeeet Caroline!!!!! I had to do a Google search to see who sang that!” — text from a guy before we went to a Sox game. He is obviously not the one for me. Extremely unfortunate, really.
There was a guy that chased me around for a couple months and we eventually went on a date. Tables turned.. I became interested and he wasn’t. Not going to lie, I was pretty bummed UNTIL a couple months later a group of us were answering the question “What are the 5 things you are most thankful for?” #3 for him: “I’m really thankful for my genes. ((silence)) You know, like genetics…” – Extremely great guy but he has not crossed my mind since.
“OH! I’ve never seen Dumb and Dumber!” — One of the very few guys I’ve ever asked out, and he is quite possibly the most awesome guy EVER … but youch… that one cut deep.
“So I have a great idea for our first date! And I hope this isn’t weird, but you’d meet my parents” ……………….. I was busy that evening 
Still a very very good friend of mine 🙂
Let’s be real though… dating stories go both ways. Some of the more epic failures on my part:
—“Hey it’s pretty cold out here, I’ll be in Bed Bath and Beyond looking at Crockpots” The guy was running late and THAT was my text to him. Let the records show that no predate text should include the word ‘Crockpot’ … or Bed Bath and Beyond for that matter. Lesson learned.
–I was on a first date with an awesome guy and started talking about being left on the side of the road on the day I thought I was being proposed to. Then I got teary eyed. Nothing says ‘let’s do this again sometime!’ better than bringing up your ex. Probably shouldn’t have been going out on dates at that point…. Awwwwwwwwwwwwkward!
–I tried to use a computer issue I had to flirt via email with the hottest guy I’ve ever known in real life. I ended my email with ‘It’ll be a Dalmatian Plantation!’ … Because what guy doesn’t love a damsel in distress that can quote 101 Dalmatians?! (For the record, it was totally relevant and funny because it rhymed with the computer error message that kept popping up on my screen)
—“I just have a lot of baggage right now that you shouldn’t have to deal with… I’d rather you be my copilot than my skycap.” Yup. That was my college self. Totally killed the mood because I couldn’t stop laughing after that, but also proud of how quickly I was able to think on my feet!! He married the next girl he dated and we are both better off 🙂
Now that I’m living in a new city I’m hoping I can (lovingly) publicize more of these incredibly awkward moments while still maintaining interest from at least SOME guys! It’s a fine line, really. In the meantime, my brother did some pretty funny posts about his worst dates… you should check them out!
The Single Life: Worst Date Countdown #3
The Single Life: Worst Date Countdown #2
The Single Life: Worst Date Countdown #1
Anyone care to share horrible dating stories? You can’t say it’s because you don’t want them to see it… I promise they don’t read my blog. LET’S HEAR SOME!
highfiverson 