Tagged: dating

True Life – I was a Stage Five Clinger, part 2.

I know, internet. I totally left you hanging right when we were getting to the juicy part.

I don’t understand how Cassandra could possibly be a Stage Five Clinger, you probably asked yourself repeatedly over the last two days. She seems like such a normal, well adjusted, fashionable, sanitary person. 

Well, you would be right, internet, and I’m modest, too. However, this is the story of how I was a Stage Five Clinger, and it’s still one of the most mortifying circumstances I’ve ever been in, so you’ll excuse me for beating around the bush.

So anyways, I had this insane crush on Cupcake, who was a year older than I was (I was 15, he was 16). We were on the same crew team (he was varsity, I was a wee novice), and I used to chat about him with my friend, Hillary Duff, using extremely clever nicknames that there was no way he would ever possibly figure out.

…of course he did. You saw that one coming, didn’t you? He totally knew. Everyone knew, apparently, and I, using my keen powers of observation, was completely oblivious to the fact that everyone totally knew about my giant crush FOR MONTHS.

Sigh. High school.

Anyways, one day after practice, Hillary Duff and I are in the parking lot talking about Cupcake, and Cupcake waltzes over and says, “Um, I know you’re talking about me.”

So of course I did Something Very Smooth.

Aka I ran for it.

Yes, Literally.

I am an embarrassment.

Luckily enough, Cupcake found my complete lack of social skills endearing, and he asked me out on a date.

Now, I mentioned before that I was a dating dummy. What I should stress now is that I was a moron, actually, because somewhere in my mind I’d managed to get the idea that going on a date with someone automatically make them your boyfriend.

No, I’m not making this up. Going on a date with someone makes them your boyfriend. I was (okay, am) socially inept. However, you have to admit it would make things much easier. No “are we monogamous?” conversations. No awkward “how do I introduce this person with using the B word?”. No dating for 2 years without changing your Facebook status. One date = boyfriend. Boom.

So we went on a date. My dad dropped me off at a local park and we went Geocaching. Never found the thing, but had a lovely afternoon. My dad picked me up. No kiss. No hug. No handholding. Not so much as a pat on the back.

I went right home and changed my Myspace status, because this was 2005 and Facebook wasn’t even a thing yet.

Oh yeah, you’re thinking, this chick is crazy. I bet she had a totally pimped out Myspace page. 

Yes, internet, I did.

And I’m not ashamed.

Yet I digress.

The very next day, Cupcake left on a week-long school trip to England.

By the time he had returned, everyone in high school thought we we dating.

Because I told pretty much everyone.

Because I’m a psychopath.

In all honesty, we could have seen this coming.

In all honesty, we could have seen this coming.

Now here comes the fun twist, internet.

Cupcake had made out with someone else on his trip. 


Now, in his defense, he knew that we weren’t actually dating, and since he’d been overseas, he didn’t know that I thought we we dating. I, however, thought he’d cheated on me.

I took to AIM the night I found out about Cupcake’s infidelity. I don’t have a transcription, but I’ll do my best.

me: how cud u?

him: ??? 😦

me: u cheated on me??!!


me: IT’S OVER!!

him: uh… okay?

Cue tears. Drama. Hysteria.

It wasn’t until almost SIX MONTHS LATER that I figured out that Cupcake and I had never ACTUALLY been a couple. And that everyone at school had secretly been laughing at me about the entire affair. And then of course I was so mortified that I couldn’t talk to the guy for three years after that.

…I’m really, REALLY oblivious.



True Life – I was a Stage Five Clinger, part 1.

I just looked at my site analytics and guess what my most popular posts are, internet? True stories about terrible, relationship related trauma.

Apparently you guys are jerks.

Anyways, I figured I’d regale you all with a tale of a young, naïve, sophomore year of high school Cassandra. Because if there is anything better than terrible stories about dating mishaps, it’s dating mishaps in high school. 

This is also the first true story I’ve told where there is any chance that the person involved could possibly read it. So if you find this, and you know who you are, you’ll know why I have to refer to you in this post as Cupcake.

I’m so sorry, Cupcake.

I should preface this tale by telling y’all that in high school, I had a very shady concept of how relationships worked. At the time of this tale, I had:

Gone on three dates with two different people, all terrible movies (Pirates of the Caribbean, Master of Disguise, Hitchhiker’s Guide to the Galaxy), and my mom came and sat in the row behind us.

Had a whirlwind month-long pseudo-relationship.

Experienced the worst kiss of my life.

However, all around me, my friends were dating people. Like, for real dating. Like, my best friend Miks totally held hands with a guy in the hallway walking to class dating. My other best friend slash mortal enemy Boomer totally made out with someone on the robotics team who had a CAR and gave her flowers for Valentine’s day DATING.

Meanwhile, I looked like this.

hnwcassandra HAIR

Ohhhh yeah. That’s some hair.

So clearly my milkshake was bringing zero boys to my yard.

I met Cupcake through mutual friends. He was a year older than me, a foot taller, and he no longer had braces. I immediately developed a HUGE crush on him.

To this day, thinking back, I still can’t put my finger on what it was that attracted me to Cupcake, as he in no way, shape, or form resembled anyone else I’ve ever have a crush on.

I think it was just that he was so freakin’ nice. Here I was, just some dorky loser sophomore, and a junior was being nice to me.


to be continued…

3 dating sites I would use if I was a Psychopath.

Welcome back to Psychopath Saturday here on hnwcassandra!

Today’s topic – dating sites.

Are you looking for love? Are you a little odd?

Okay, are you clinically insane?

These three sites may be for you!

1. Darwin Dating.

Are you kind of an asshole? Are you a massive egotist? How many hours, on average, do you spend obsessing over your personal appearance? Most of them?

If you’re like our friends over at Darwin Dating, you too can hone your search for love by using only the shallowest of criteria. According to their website, “Attractive people are at a disadvantage on normal internet dating sites. They have to wade through a plethora of ugly people and ugly people pretending to be attractive in order to find someone who matches their own attractiveness.”

That’s why ugly people are banned from using their site. How do you know if you’re too ugly to join? Because you get rated by their members.

They also have an extensive list of “ugly” qualities, including red hair, acne, and fat rolls.


2. Meet-An-Inmate.

Meet-An-Inmate.com caters to those who like to live on the wild side. They recognize that certain women have a predilection for bad boys.

Specifically, criminals.

Some of these inmates have extremely creative profiles.

Take Casey’s, for example.

At nights,  I’ll look out my cell window and sometimes an owl appears. At times, he will look up at me and I can see his striking eyes. Especially when it’s a full moon night. His eyes are like shiny diamonds, kind of like the eyes of a cat. Some nights it looks as if he has steam on his brow, I wonder what it would be like to be that own, to actually see what he sees, to be free, or even be able to talk to that owl. Sometimes he will give me that stare, like he wants to say you’ve came looking for trouble and here it is. As I sit here pondering the quandary I’m in. Friendships have come and gone. My desire to build strong relationships and good friendships.

That’s beautiful, Casey.

Very strange, but beautiful.

The website does have a disclaimer, saying, “by using this service, you agree to not hold us responsible for any costs, liabilities, attorney’s fee or damages that you may incur”.

Y’know, from becoming romantically involved with a convicted felon.

3. Can Do Better.

Can Do Better is the site for people who are already in relationships, but are either very insecure or are looking to move on and are unwilling to leave without another option in the bag.

It’s a site where you can put up pictures of you and your partner and people vote on whether or not you can do better. And then you can pick someone else from the Can Do Better pile.

I can’t even.

3 Craigslist ads I would reply to if I was a psychopath.

Guess what internet. It’s the long anticipated sequel to Psychopath Saturday. The first Psychopath Saturday was actually on a Sunday, but this is my blog and I do what I want.

These are actual, live, unedited Craigslist posts. They are all from places far away from me. Partially because I was too scared to look at the personal ads for my own area, but mostly because if any of these people read this, I don’t want them to be able to hunt me down.

hnw cassandra sherlock


hello – 20

Hey what’s up with it just looking for a good friemd to talk to and hamg out with so if that u and ur.young like me and want to make a new.hang out friend then get at me amd we can go from there anyways you should live close to *** and.be around my age and looking for a new friend to talk to and want to hang out with so if u want to get to know me then text me or email me and we can go from there *** six eight eight seven three 11 thanks hope o hear from u*** Note – I did take out the area code and location here, but if you are curious, click through to the original post.

Yes. YES. Starting off with a strong contender here. The creative spelling, the fact that they used the word “friend” three times, the inclusive of a phone number (!!!). This person is clearly a bold, entrepreneurial genius. He’s a rebel. He learned spelling and grammar (maybe?) and thought to himself No. I shall make my own way in life. The inclusive of a phone number speaks to a dangerous streak. This guy doesn’t play by the rules. He makes the rules.

So, yes, I may be selfish and self-centered, BUT… – 30 
...well, that’s pretty much it. Scratch the but.I’m visiting Craigslist as a convenient venue for meeting cool new people. In my normal social circles it’s the same people with different names, but on Craigslist, you never know what you’ll find.Before you start writing me – and I know you’re already having trouble resisting- understand that probably won’t write you back, partly because I don’t have time to sift through the torrent Craigslist produces and partly because I’ll have stopped caring by the time I get around to reading my mail.That said, you *should* write me because I’d like the option of hanging out if you happen to be cool or exceptionally attractive.Knowing that, you really should focus on writing something I won’t fall asleep reading.You should be open to meeting in person in the near future; if you’re too timid to exchange numbers, this isn’t the ad for you.Email me. Include an embarassing story I can use later.

This guy knows what he’s looking for. Cool people with embarrassing stories. Is that you? Probably not. But maybe. Try emailing him. He’ll write back. Or he won’t. He cares. Ish.

You know what women go crazy for? A man who plays hard to get. Someone who reminds them of their super cool high school boyfriend who, like, was so above caring, y’know? This person is cool and he knows it. He doesn’t even have to convince you. He already hooked you by the promise that he might write back. Or not. Whatever.

Baby Maker Still Wanted- 63

I am looking for a fertile woman to start a family. I’m 63, well educated, in good physical condition, and I think good looking (that would be for you to decide).You should be loving and family oriented.

I believe children should be raised by both parents, so if you think the father should

not be around, please do not respond. I am in this for the long run.

If interested, put “Family Time” in the subject line to avoid spam, or you will be deleted.

Thanks, and may God bless you.

This guy ain’t afraid to go for the jugular. He wants kids, and what he needs is a working womb. No personality required. Baby maker? That’s the endearment I want to be referred to by my man. He doesn’t even mention marriage. It’s the 21st century.

Marriage is so passé.

What do you think, internet? If you had to pick from one of these fine gentlemen which one would you go for?

The true story of the worst kiss of my life.

So I’ve been watching my stats recently, internet. Don’t you think I haven’t been.

These are the top ten posts of all time out of the last 82 posts (this is post 83, can you believe it?) along with their page views:

The WORSER worst date I’ve ever been on. 115
The true story of the first night I ever went out drinking, part 1. 103
Women’s Strength Training Anatomy – a review. 93
The worst meal I’ve ever had. 80
Friend dating. 72
Justin Bieber is not a douchebag. 68
Here goes nothing. 67
The true story of the worst date I’ve ever been on. 66
Grad school in memes. 65
My cat’s on Prozac. 64

Look at this list, internet. A lot of worsts. Dating. Drinking. Debauchery. And of course, memes and cats.


I figured today, given your preferences, I’d do a crowd-pleasing post about The Worst Kiss I’ve Ever Experienced. It’s a short but bittersweet tale.

Our story today takes place in a little pseudo-town called Govy (Government Camp). On Wikipedia Govy is referred to as an unincorporated community, whatever that means. It’s essentially a slap-dash ski town that has three or four different ski camps, 6 or 7 different demo shops, a pizza place, an ice cream shop, and a diner. That’s essentially it. If they have police or a fire department, you’d never know it (unless you were involved in a firecracker war with the dishwashers who worked at the Huckleberry in diner, but that’s a different story for a different time).

I went to a ski camp there in the summer of ’05 called MHSSC. It was a ski/ snowboard training program run off of the nearly mountain Mt. Hood (Fun fact- the hotel that The Shining was filmed in, the Timberline Lodge, is located at the base of this mountain. Awesome). It was a two week program where you got to train during the mornings on the glacier until the snow started to melt around noon, and then in the afternoons we got into plenty of debauchery and craziness and shenanigans like surfing and hiking and white water rafting and whatnot.

This is an actual picture of me from that summer, courtesy of Hubs. I figure if I put all of my least attractive pictures online myself, my family will have less blackmail fodder later down the road.

This is an actual picture of me from that summer, courtesy of Hubs. I figure if I put all of my least attractive pictures online myself, my family will have less blackmail fodder later down the road.

I was 15. I had, in fact, kissed some people. I had even french-kissed someone. I had bypassed the cootie contamination issue, but I was by no means experienced in the ways of love. Coming off of my first year in high school, I’d already fancied myself old and wise and had had my heart broken by my boyfriend of 37 seconds (it was meant to be, but alas, someone else’s boobs came in before mine did).

I was, however, not ready for the whirlwind of hormones that awaited me at Govy.

I met Murphy MacManus the first day of camp. He was tall and Irish and had blue braces and sunburnt skin. His voice crackled like feedback on a microphone. He even had a few ginger hairs growing on his scrawny torso. I was in love (probably).

Our whirlwind romance lasted an entire 3 days, which in summer camp time, is practically a year. He even let me share his headphones when we listened to music on his Discman on the bus. What we had was real. 

Sadly, it was not to be. We went on a date after white-water rafting one night to the Huckleberry Inn Diner. I bought us a huckleberry milkshake to share and a piece of huckleberry pie. To this day that pie ranks on my top five pies of all time (piemakers 1-3, you know who you are).

The huckleberry shake was so good we ended up ordering a second.

That’s where it all went downhill.

Full and satisfied, we walked down the street homewards when Murphy MacManus grabbed me and locked me in a passionate embrace, and what should have been the highlight of my teenette life took a rapid turn as his kiss deepened. First of all, he was about a foot taller than me, so he had to bend down at an awkward and frankly unreasonable angle. Secondly, oh my goodness, he used his tongue like someone trying to get the last little bit of peanut out of a jar. I mean, I don’t want to get too graphic here, but his tongue was in it to win it. Thirdly, I cut my lip on his braces. Fourthly, I was full of milkshake.

I pulled away from him but it was too late. His passionate kiss had triggered my gag reflexes. I spewed huckleberry milkshake all over my American Eagle flip flops.

It remains the 3rd most embarrassing moment of my life.

Poor Murphy MacManus gallantly helped me back to my dorm room, but the moment was ruined forever.

Ah, young love.


The WORSER worst date I’ve ever been on.

Seriously. I just posted a blog about the worst date I’d ever been on. It’s barely been two weeks since I wrote the blog.

Oh, but internet, just last night the worst date I’ve ever been on was gloriously and theatrically upstaged. It was the Emperor of worst dates. If worst dates were Disney villains, this was Scar. If worst dates were Doctor Who baddies, this was Dalek Caan. If worst dates were unfortunate situations, this date was freshly buttered toast dropped upside-down onto a fraternity floor and you’re out of bread. 

You get the picture.

I have a part-time job as a caterer for a local catering company. I get to do a lot of things for this job, but I’m generally put on the bar because I’m both over 21 and a fairly decent multi-tasker. Last night, I was working the bar for a reception at the local university. It was some big-shot symposium on sustainable architecture or something, and most of the attendees were students and grad students enrolled at the school. I get put on architecture gigs a lot for some reason, so I knew the building and a lot of the students and the professors and it was a pretty relaxed event. I got to chitchat a fair amount with the people coming in.

So this guy kept coming over and I had to open his beer bottles and whatnot, and we had a choppy conversation, but the conversations I had with people were sort of running together because I had to interact with so many people. He was kind of cute, but not really my type, and at the rate at which I had to keep opening bottles of cabernet, I really was not paying attention to what he looked like anyways.

At the end of the night, I was breaking everything down with my coworker as the remaining 5 or so people were straggling out, and he came over (let’s call him James Franco) and said to me that there was a party at a bar downtown that he was going to and his friends egged him on to ask me out to it. Usually I go out with my friends to our usual bar where we sit in the same corner and drink the same drinks on Saturdays, but heck, why not. So I said yes.

After the van was unloaded and the catering business was put to bed, I got home and called my girl Varenka and convinced her that she really needed to put pants on and be my wing-girl, so she convinced her man-toy (let’s call him Rory) to come out with us for an hour. I texted James Franco and he said he was going to the club with his friends at 10 and he’d see me there. Cool beans.

V-renks and Rory and I rolled in around 10:30. No James Franco. It was pretty dead for a Saturday in there and it was NOT our scene. It was like walking into one of those crazy posh theme bars they make fun of in sitcoms. Everything was artfully grunged and buffed and destroyed and polished and painfully hip, and there were two 40 year old virgins playing techno in the corner surrounded with so many strobe lights they both had to wear sunglasses. Yet we persevered and ordered a very overpriced round of weak cocktails with lots of fancy garnishes on them.

This dude didn’t even show up until 11:15, which you may note was over an hour late. He came solo and mistook another Asian girl as me, which was as painfully awkward as you could imagine. He shook Varenka’s and Rory’s hands and sat next to me on a very hip vegan leather couch and balanced his tiny cocktail on the very hip patina’d metal chest that was there instead of a table.

James Franco did everything wrong. Everything. Even forgetting that he was an hour late and his friends never showed up. To sum:

– Tactless Asian jokes he tried to justify by indicating amount of time spent with Asians- check.
– Lying about his age (27) – check.
– Conveniently forgetting to mention he wasn’t a student here- check.
– Telling me he was only in town for four days and that he was “looking for a good time”- check.
– Asking me where I lived and how I was getting home (!!!) – check check.
– Being boring and awkward- the most checks.

Varenka and Rory left around 11:30, and I tried – really I did try – to not hate the entire experience, but between the awful music and the awful atmosphere and the fact that he bought me a Jack and Ginger instead of a Jameo Ginger and kept inching closer to me on the awful couch, I just couldn’t do it. So I pulled the Midnight Cinderella routine, refused the company back to my car (!!!), and lit outta there like the prizewinner at the Kentucky Derby.

The clincher, I think, was the follow up text I got this morning asking if I was around to “hang out” tonight. No, James Franco. I moved to Siberia. Find some other floozy to unimpress.

That’s the last time I go out to a hipster bar with a lying, pervy architect. Ugh. Never again, internet.

The true story of the worst date I’ve ever been on.

This story is meant as a cautionary tale for fellas who want to woo a special lady. It’s not great to under impress a girl, but it’s even worse to overshoot the landing.

I will say as a preface that I was really rooting for this one to work out. It happened a little over three years ago when I was going through a bit of a rough patch in life, having just broken up with my first “real” boyfriend of sorts.  I will not name names, but for clarity I will refer to him as one of my favorite actors.

Morgan Freeman was a fraternity president, an accomplished musician, a chef, and a very accomplished scholar. We met at a pageant of sorts in which I was playing the ukulele and he was playing the guitar. I’m pretty sure he won. I came in second. No, I’m not making this up.

Just like this.

Just like this.

Anyways, Morgan Freeman and I totally hit it off, and push comes to shove, he invited me back to his room in the frat to play music.

Calm yourselves, internet, nothing untoward happened. We actually played music. Beatles, mostly.

It was really nice. I had a fantastic time. We were jiving and the conversation was flowing and all that good jazz. I remember being impressed because his room was ridiculously impressive for a frat house, and I think he told me his mom was an interior decorator or something like that. Super posh. I went home to my fantastic roommate all revved up, and then we probably watched a hockey game and ate goldfish and drank a really horrible cocktail and went to bed or something.

So Morgan Freeman texted me the next day asking me if I’d like to do dinner. And that’s when Things Went Downhill. Because of course I said yes, and in my head I was picturing a slice of pizza, and if things got really impressive, ice cream. And in his head there was apparently a 5 course candlelit meal with a string quartet and a dozen roses.

Gentlemen, here’s some life advice. Impressing women is not always about buying the gal roses and champagne. Sometimes, it’s about knowing whether or not she even likes roses and champagne, or if she’d far prefer dandelions and an ice cold beer.

I’m mostly a dandelions and beer kind of girl. So when Morgan Freeman told me he wanted to cook dinner, I said okay, but I was a little apprehensive. Then when he told me he was planning on making a blueberry wine marinated rack of lamb with an impressive assortment of sides, I said I’d make dessert, when what I really meant was You’re cooking what now? 

This is the part where some of you are shaking your heads and thinking I’m an ungrateful snot. Maybe I overreacted slightly, but in my mind, the first date is about getting to know each other, not impressing your date with a crazy meal, especially if your date knows about as much about making dessert as a business executive in L.A. probably knows about ice fishing. Let’s just say that I stressed out about what I was going to make the entire meal and when the chocolate mousse I decided to make (I was so naive) was about as cooperative as a cat in a bathtub, I was in full panic mode.

Meanwhile, Morgan Freeman was waltzing about my tiny kitchen with the grace of a true pageant winner, going on and on about exotic cheeses, and I felt so out of my element that I kept adding vodka to my screwdriver. It didn’t help that he showed up in a button down shirt with a nice sweater and pressed khakis (!!!) and I hadn’t even bothered to brush my hair.

So good.

Oh Morgan. You don’t have to cook to impress me.

Add to this scene my pajamaed roommate running in and out grabbing things from her pile of school books, the neighbours having some sort of rave next door, and the fact that my notoriously finicky oven kept misbehaving. By the time the food was ready to eat, I was already tipsy, we had run out of conversation starters, and my mousse had lost what little stamina I’d managed to beat into it and had melted into a goopy puddle. Disaster.

Happily, the meal he’d prepared was really, really good. Unhappily, we we both so stressed out and on edge that we barely touched it.

Like a true gentleman, he rallied to my deflated mousse, but by the time we parted ways with one of those awkward hug – handshake – only-one-person-goes-in-for-a-kiss situations, I’m pretty sure we were both ready to call it a night.

Moral of the story – Dudes, know your ladies. Pick something out for a date that puts both of you in a non-stressful situation. And if you ever have to “just whip up” a dessert, for the love of all that is holy DO NOT try to make mousse.