Caffeine Confidential: The Best of the Worst

Want to know how this whole Dating Diary began? Start here.

I feel like there are two perspectives from which most dating stories come from: a rant of the absolutely atrocious, and a ballad of the struggles that led to true love. This, and my experiences, are neither. I’m still single. There have been less than ideal dates, but nothing truly awful. This is from a perspective of self-empowerment.

But I know the awful shit is the funny part… you want to read and cringe along and be thankful it isn’t you. Guess what? It’s even better if you can find the hilarity in your own situations and laugh at yourself. I like to think of it as character building. So, without further ado, the best of the worst parts of those dates.

Most awkward and hilarious of all is the guy who told me he thought I had autism. We had been texting prior to setting plans to meet up, and I inevitably threw out my favorite bitchy call-to-action: “hey, do you want to meet for a drink or coffee? I don’t want to text a pen pall for 3 weeks… I can usually tell if I’m into someone after just meeting.” (Remember that whole personal challenge about how un-apologetically “me” I can be? Testing, testing…) I followed it up by mentioning that I didn’t mean that harshly, and just have a hard time with subtlety (as anyone who remotely knows me is already aware). We met for drinks a couple nights later at a bar in my neighborhood, and at one point the man next to us asked about our first date and what word the dude would use to describe me. He said I’m endearing in person… and should have just shut up right there. Of course, then I wouldn’t have a story to laugh at myself about every time I drink wine with my roommates. He continued to tell me that when I told him I have a hard time with subtlety, he had to give himself a pep talk because he’d never been on a date with a girl with autism or Asperger’s before. Apparently after meeting me he realized that I am neither… I promptly chugged my wine.

Then there was the guy who had all the potential in the world (Italian, super smart, charismatic, attractive, gentlemanly, fun…) but ended up trying to shove his face on mine and make out at least 10 times at a dive bar when his ex girlfriend showed up. My frustrations with having to push him away and leave ended up on Twitter (my sorority would be so disappointed; so little has changed since undergrad). Of course, my life is a joke and the story can’t end there… his friends saw my Twitter rant and not only sent it to him, but I apparently have a group chat fan club of 20-something men talking shit about how I’m crazy. (Update: they’ve since found this blog and let’s just say the reactions were also not positive.)

Then there was the guy who told me my “cackle” of a laugh was adorable. The guy from Tinder who asked for my Instagram account and immediately stopped messaging me back after looking at my account (is it THAT bad?). The guy who took me to dinner, found out I hated milk, informed me his family runs a large milk distributor in Florida, and never messaged me again. I guess my dairy preferences just took things too far.

So, yes, sometimes parts of dates go badly. Sometimes people disappoint you, or point out things they find less than wonderful about you. Maybe you’re also self conscious of your dorky laugh or a little insecure of your crippling awkwardness. It definitely sucks having drama spring up around speaking out or standing up for yourself. But here’s the thing…

Not everyone will like you. Not everyone will agree with you. Everyone has their own non-negotiables, and their own preferences for a partner, and you’re not going to meet all of those. Just like so many people will not meet those for you. That’s okay… because unlike pairs of jeans or girlfriends, where we can have multiple variations in our lives with different levels of suitability… we only need one “person”. (Let’s just not get into polyamourous/open relationships right now because my head hurts just texting more than one guy at a time.) Only one of the 7 billion people on this planet needs to fit (and if you’re my Tinder match who thinks spaceship-green-headed-aliens-contacting-Earth are real, you have even more options!)

So thank you, attractive-Italian-makeout-boy, for reminding me that despite my love for affection, I am still in control of who I give it to and when. (Also thanks for the site views, PhanClub!) Thank you, Instagram Creeper, for not wasting both of our time after decided that whatever it was about the lifestyle I portray on social media doesn’t align with yours. Until that one-in-seven-billion happens, I get to spend every day in love with my own sense of humor, and ability to laugh at my own life in a dorky cackle, and my loud-mouth, unfiltered bluntness.


The original posted earlier this week cut off the ending of the post, which is sort of the entire point of this. I blame the coffee-shop wifi. I’ve since updated it to add in the remainder of my point, because this was never about shit-talking men. I’ve also added a few comments in italic parentheses throughout the original, courtesy of my giant mouth and lack of fucks given. 
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